UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549
FORM N-CSR
CERTIFIED SHAREHOLDER REPORT OF REGISTERED MANAGEMENT INVESTMENT COMPANIES
Investment Company Act file number 811-21982
Guggenheim Strategic Opportunities Fund
(Exact name of registrant as specified in charter)
227 W. Monroe Street, Chicago, IL 60606
(Address of principal executive offices) (Zip code)
Amy J. Lee
227 W. Monroe Street, Chicago, IL 60606
(Name and address of agent for service)
Registrant's telephone number, including area code: (312) 827-0100
Date of fiscal year end: May 31
Date of reporting period: June 1, 2016 - November 30, 2016


 
Item 1.  Reports to Stockholders.
The registrant's semi-annual report transmitted to shareholders pursuant to Rule 30e-1 under the Investment Company Act of 1940, as amended (the “Investment Company Act”), is as follows:


 

GUGGENHEIMINVESTMENTS.COM/GOF
... YOUR WINDOW TO THE LATEST, MOST UP-TO-DATE
INFORMATION ABOUT GUGGENHEIM STRATEGIC
OPPORTUNITIES FUND
The shareholder report you are reading right now is just the beginning of the story.
Online at guggenheiminvestments.com/gof, you will find:
·  Daily, weekly and monthly data on share prices, net asset values, distributions and more
 
·  Portfolio overviews and performance analyses
 
·  Announcements, press releases and special notices
 
·  Fund and adviser contact information
Guggenheim Partners Investment Management, LLC and Guggenheim Funds Investment Advisors, LLC are continually updating and expanding shareholder information services on the Fund’s website in an ongoing effort to provide you with the most current information about how your Fund’s assets are managed and the results of our efforts. It is just one more small way we are working to keep you better informed about your investment in the Fund.


   
(Unaudited) 
November 30, 2016 
 
DEAR SHAREHOLDER
We thank you for your investment in the Guggenheim Strategic Opportunities Fund (the “Fund”). This report covers the Fund’s performance for the six-month period ended November 30, 2016.
The Fund’s investment objective is to maximize total return through a combination of current income and capital appreciation. The Fund pursues a relative value-based investment philosophy, which utilizes quantitative and qualitative analysis to seek to identify securities or spreads between securities that deviate from their perceived fair value and/or historical norms. There is no guarantee that the perceived fair value will be achieved. The Fund’s sub-adviser seeks to combine a credit-managed fixed-income portfolio with access to a diversified pool of alternative investments and equity strategies.
All Fund returns cited—whether based on net asset value (“NAV”) or market price—assume the reinvestment of all distributions. For the six-month period ended November 30, 2016, the Fund provided a total return based on market price of 15.76% and a total return based on NAV of 13.58%. NAV return includes the deduction of management fees, operating expenses, and all other Fund expenses.
As of November 30, 2016, the Fund’s market price of $19.22 represented a premium of 2.56% to its NAV of $18.74. The market value of the Fund’s shares fluctuates from time to time and may be higher or lower than the Fund’s NAV. Past performance is not a guarantee of future results.
From June 2016 through November 2016, the Fund paid a monthly distribution of $0.1821. The latest distribution represents an annualized distribution rate of 11.37% based on the Fund’s closing market price of $19.22 on November 30, 2016. The Fund’s distribution rate is not constant and the amount of distributions, when declared by the Fund’s Board of Trustees, is subject to change based on the performance of the Fund. Please see Note 2(i) on page 50 for more information on distributions for the period.
Guggenheim Funds Investment Advisors, LLC (the “Adviser”) serves as the investment adviser to the Fund. Guggenheim Partners Investment Management, LLC (“GPIM” or the “Sub-Adviser”) serves as the Fund’s investment sub-adviser and is responsible for the management of the Fund’s portfolio of investments. Each of the Adviser and the Sub-Adviser is an affiliate of Guggenheim Partners, LLC (“Guggenheim”), a global diversified financial services firm.
We encourage shareholders to consider the opportunity to reinvest their distributions from the Fund through the Dividend Reinvestment Plan (“DRIP”), which is described in detail on page 71 of this report. When shares trade at a discount to NAV, the DRIP takes advantage of the discount by reinvesting the monthly dividend distribution in common shares of the Fund purchased in the market at a price less than NAV. Conversely, when the market price of the Fund’s common shares is at a premium above NAV, the DRIP reinvests participants’ dividends in newly-issued common shares at the greater of NAV per share or 95% of the market price per share. The DRIP provides a cost-effective means to accumulate additional shares and enjoy the benefits of compounding returns over time. Since the Fund endeavors to maintain a stable monthly distribution, the DRIP effectively provides an income averaging technique
 

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 3 


   
(Unaudited) continued 
November 30, 2016 
 
which causes shareholders to accumulate a larger number of Fund shares when the market price is depressed than when the price is higher.
To learn more about the Fund’s performance and investment strategy, we encourage you to read the Questions & Answers section of this report, which begins on page 5. You’ll find information on GPIM’s investment philosophy, views on the economy and market environment, and detailed information about the factors that impacted the Fund’s performance.
We appreciate your investment and look forward to serving your investment needs in the future. For the most up-to-date information on your investment, please visit the Fund’s website at guggenheiminvestments.com/gof.
Sincerely,

Donald C. Cacciapaglia
President and Chief Executive Officer
Guggenheim Strategic Opportunities Fund
December 31, 2016

4 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
QUESTIONS & ANSWERS (Unaudited) 
November 30, 2016 
 
Guggenheim Strategic Opportunities Fund (“Fund”) is managed by a team of seasoned professionals at Guggenheim Partners Investment Management, LLC (“GPIM”). This team includes B. Scott Minerd, Chairman of Guggenheim Investments and Global Chief Investment Officer; Anne B. Walsh, CFA, JD, Senior Managing Director and Assistant Chief Investment Officer; James W. Michal, Senior Managing Director and Portfolio Manager; and Steven H. Brown, CFA, Managing Director and Portfolio Manager. In the following interview, the investment team discusses the market environment and the Fund’s performance for the six-month period ended November 30, 2016.
What is the Fund’s investment objective and how is it pursued?
The Fund seeks to maximize total return through a combination of current income and capital appreciation. The Fund pursues a relative value-based investment philosophy, which utilizes quantitative and qualitative analysis to seek to identify securities or spreads between securities that deviate from their perceived fair value and/or historical norms. There is no guarantee that the perceived fair value of the Fund’s portfolio investments will be achieved.
GPIM seeks to combine a credit-managed fixed-income portfolio with access to a diversified pool of alternative investments and equity strategies. The Fund seeks to achieve its investment objective by investing in a wide range of fixed-income and other debt and senior-equity securities (“Income Securities”) selected from a variety of credit qualities and sectors, including, but not limited to, corporate bonds, loans and loan participations, structured finance investments, U.S. government and agency securities, mezzanine and preferred securities and convertible securities, and in common stocks, limited liability company interests, trust certificates, and other equity investments (“Common Equity Securities,” exposure to which is obtained primarily by investing in exchange-traded funds, or ETFs) that GPIM believes offer attractive yield and/or capital appreciation potential, including employing a strategy of writing (selling) covered call and put options on such equities. GPIM believes the volatility of the Fund can be reduced by diversifying across a large number of sectors and securities, many of which historically have not been highly correlated to one another.
Under normal market conditions:
·
The Fund may invest without limitation in fixed-income securities rated below investment grade (commonly referred to as “junk bonds”); the Fund may invest in below-investment grade income securities of any rating;
 
·
The Fund may invest up to 20% of its total assets in non-U.S. dollar denominated fixed-income securities of corporate and governmental issuers located outside the U.S., including up to 10% of total assets in fixed-income securities of issuers located in emerging markets;
 
·
The Fund may invest up to 50% of its total assets in common equity securities, and the Fund may invest in exchange-traded funds (“ETFs”) or other investment funds that track equity market indices and/or through derivative instruments that replicate the economic characteristics of exposure to Common Equity Securities; and


GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 5

 
   
QUESTIONS & ANSWERS (Unaudited) continued 
November 30, 2016 
 

·
The Fund may invest up to 30% of its total assets in investment funds that primarily hold (directly or indirectly) investments in which the Fund may invest directly, of which amount up to 30% of the Fund’s total assets may be invested in investment funds that are registered as investment companies under the Investment Company Act of 1940 (the “1940 Act”) to the extent permitted by applicable law and related interpretations of the staff of the U.S. Securities and Exchange Commission.
GPIM’s process for determining whether to buy a security is a collaborative effort between various groups including: (i) economic research, which focus on key economic themes and trends, regional and country-specific analysis, and assessments of event-risk and policy impacts on asset prices, (ii) the Portfolio Construction Group, which utilize proprietary portfolio construction and risk modeling tools to determine allocation of assets among a variety of sectors, (iii) its Sector Specialists, who are responsible for identifying investment opportunities in particular securities within these sectors, including the structuring of certain securities directly with the issuers or with investment banks and dealers involved in the origination of such securities, and (iv) portfolio managers, who determine which securities best fit the Fund based on the Fund’s investment objective and top-down sector allocations. In managing the Fund, GPIM uses a process for selecting securities for purchase and sale that is based on intensive credit research and involves extensive due diligence on each issuer, region and sector. GPIM also considers macroeconomic outlook and geopolitical issues.
The Fund uses financial leverage (borrowing and reverse repo) to finance the purchase of additional securities. Although financial leverage may create an opportunity for increased return for shareholders, it also results in additional risks and can magnify the effect of any losses. There is no assurance that the strategy will be successful. If income and gains earned on securities purchased with the financial leverage proceeds are greater than the cost of the financial leverage, common shareholders’ return will be greater than if financial leverage had not been used. Conversely, if the income or gains from the securities purchased with the proceeds of financial leverage are less than the cost of the financial leverage, common shareholders’ return will be less than if financial leverage had not been used.
What were the significant events affecting the economy and market environment over the past six months?
Behind the performance numbers for the past six months are a multitude of events that unfolded throughout 2016, including an increase in U.S. corporate default volume, several quarters of negative earnings growth, the British vote to exit the European Union, and stubbornly low inflation across the globe. That was on top of one of the worst selloffs for U.S. corporate bonds since the financial crisis in the first six weeks of the year, or that the S&P 500 was down almost 11%. We continue to believe that the turnaround in market performance was a result of global central bank easing.
The surprise end to the fractious U.S. election season leaves many questions unanswered about the new administration, but as it relates to the economy we are particularly alert to the possible market impact of resurgent fiscal policy. We will learn more as we move through the transition of power, but in the meantime several market positives should support asset performance in 2017. The domestic economy just turned in the highest growth rate in two years, early indications point to a strong Christmas selling season, corporate earnings have rebounded, and the energy sector is stabilizing with the oil market recovery.
 

6 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
QUESTIONS & ANSWERS (Unaudited) continued 
November 30, 2016 
 
U.S. real gross domestic product (GDP) grew by 3.2% in the third quarter, according to the second reading, up from 1.4% in the second quarter. We expect output to rise by around 2% on average in coming quarters, a bit faster than the trend rate over the past year, as drags from past dollar strength and an inventory adjustment cycle fade. The policy outlook has become more uncertain with the election, though early indications that fiscal easing will be prioritized in the new administration suggest that the risks to real GDP growth in 2017 and 2018 are now skewed to the upside.
The labor market continues to strengthen and the unemployment rate declined by just 0.4 percentage point to 4.6%, but labor force participation has not grown as much as hoped, and started to trend downwards in November. In the year through November, the labor force participation rate increased by just 0.1 percentage point. Job openings data, another measure of labor market health, has been looking better.
In November of 2015 it was about 5.2 million job openings for the month. By November 2016, it had risen to a little more than 5.5 million job openings for the month. A higher level of job openings tends to indicate a more robust labor market.
GPIM expects the U.S. Federal Reserve (the “Fed”) policymakers to follow their recent rate increases (including a quarter-point increase in the key rate on December 15, after the period ended) with three, and possibly four, more hikes in 2017. While this would be faster than markets are now pricing in, it would still leave rates below levels prescribed by standard policy rules. Fed Chair Janet Yellen commented recently about temporarily running a “high-pressure economy” in the hope that enabling robust business activity and a tight labor market may result in an increase in the productive capacity of the economy. If this scenario materializes, it could entail unemployment dropping further, and inflation overshooting the Fed’s 2% goal. This perspective, as well as the president-elect’s proposed changes to fiscal policy and the likely impact to future real rates, accounts for much of the backup in long-term interest rates, although ongoing asset purchase programs by the European Central Bank (ECB) and Bank of Japan (BoJ) will likely continue to support bond prices. The monetary policy divergence will continue to support the U.S. dollar.
How did the Fund perform for the six months ended November 30, 2016?
All Fund returns cited—whether based on net asset value (“NAV”) or market price—assume the reinvestment of all distributions. For the six-month period ended November 30, 2016, the Fund provided a total return based on market price of 15.76% and a total return based on NAV of 13.58%. NAV return includes the deduction of management fees, operating expenses, and all other Fund expenses.
As of November 30, 2016, the Fund’s market price of $19.22 represented a premium of 2.56% to its NAV of $18.74. As of May 31, 2016, the Fund’s market price of $17.61 represented a premium of 0.63% to its NAV of $17.50. The market value of the Fund’s shares fluctuates from time to time and may be higher or lower than the Fund’s NAV. Past performance is not a guarantee of future results.
From June 2016 through November 2016, the Fund paid a monthly distribution of $0.1821. The latest distribution represents an annualized distribution rate of 11.37% based on the Fund’s closing market price of $19.22 on November 30, 2016. The Fund’s distribution rate is not constant and the amount of
 

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 7


   
QUESTIONS & ANSWERS (Unaudited) continued 
November 30, 2016 
 
distributions, when declared by the Fund’s Board of Trustees, is subject to change based on the performance of the Fund. Please see Note 2(i) on page 50 for more information on distributions for the period.
Discuss performance over the period.
During the period, the Fund saw positive performance primarily attributable to the continued tightening of credit spreads across fixed income sectors, as well as the Portfolio’s high carry. The credit rally continued through the period despite one of the worst selloffs in government bond markets since the 2013 taper tantrum. Return from spread tightening during the period was chiefly driven by the Portfolio’s investments in collateralized loan obligations (“CLO”), bank loans, and high yield corporate bonds.
The CLO market rebounded during the period. Volatility during early 2016 kept many CLO issuers on the sidelines. As a result, traditional CLO debt investors entered the third quarter well behind internal CLO spending targets. Adding to demand, investors continued to increase allocations to floating-rate CLO debt in response to rising USD LIBOR and negative yields in Japan and Europe. Not surprisingly, CLO spreads tightened significantly during the period. Already hoping to issue or refinance CLOs ahead of the December 2016 risk retention deadline, CLO issuers were only too happy to meet strong CLO demand. September represented the highest monthly CLO issuance since June 2015.
Bank loans and high-yield bonds delivered strong returns during the period. Generally, the biggest gains came from lower quality assets. Bank loan discount margins have tightened and prices have been buoyed by strong collateralized loan obligations (“CLO”) demand and loan mutual fund inflows. In fact, S&P Leveraged Commentary & Data shows that visible demand for loans has outpaced net supply for the longest such stretch since 2009.
The high-yield corporate bond market market followed a fairly predictable path. The continuation of a depressed commodity-price environment ultimately pressured earnings in oil, gas and metals, causing a wave of defaults to materialize. Based on the 1998 default cycle, we predicted that defaults would peak in 2016. Since peaking at 5.7 percent in August, 12-month trailing default rate for all U.S. speculative-grade borrowers rated by Moody's has fallen to 5.5 percent. It is expected to decline further in 2017.
Given the upward trend in the 10-year U.S. Treasury note and the anticipation of three to four additional rate hikes in 2017, over half of the Portfolio has been floating rate with limited interest rate duration risk.
Discuss the Fund’s approach to duration.
Although the Fund has no set policy regarding portfolio duration or maturity, the Fund currently maintains a low-duration target, but adds opportunistically to attractive long duration assets when it can take advantage of short-term fluctuations in interest rates.
What is the Fund’s leverage strategy?
Since leverage adds to performance when the cost of leverage is less than the total return generated by investments, the use of leverage detracted from the Fund’s total return during this period. The purpose
 

8 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
QUESTIONS & ANSWERS (Unaudited) continued 
November 30, 2016 
 
of leverage (borrowing and reverse repo) is to fund the purchase of additional securities that provide increased income and potentially greater appreciation to common shareholders than could be achieved from an unlevered portfolio. Leverage results in greater NAV volatility and entails more downside risk than an unleveraged portfolio.
As of November 30, 2016, the amount of leverage was approximately 31% of total managed assets. GPIM employs leverage through two vehicles: reverse repurchase agreements, under which the Fund temporarily transfers possession of portfolio securities and receives cash which can be used for additional investments, and a committed financing facility through a leading financial institution. There is no guarantee that the Fund’s leverage strategy will be successful. The Fund’s use of leverage may cause the Fund’s NAV and market price of common shares to be more volatile and can magnify the effect of any losses.
Index Definitions
Indices are unmanaged and reflect no expenses. It is not possible to invest directly in an index.
The Standard & Poor’s 500 Index is a capitalization-weighted index of 500 stocks. The index is designed to measure performance of the broad domestic economy through changes in the aggregate market value of 500 stocks representing all major industries.
The Bloomberg Barclays U.S. Aggregate Bond Index is a broad-based flagship benchmark that measures the investment grade, U.S. dollar-denominated, fixed-rate taxable bond market, including U.S. Treasuries, government-related and corporate securities, mortgage-backed securities or “MBS” (agency fixed-rate and hybrid adjustable-rate mortgage, or “ARM”, pass-throughs), asset-backed securities (“ABS”), and commercial mortgage-backed securities (“CMBS”) (agency and non-agency).
The Bloomberg Barclays U.S. Corporate High Yield Index measures the U.S. dollar-denominated, high yield, fixed-rate corporate bond market. Securities are classified as high yield if the middle rating of Moody’s, Fitch, and S&P is Ba1/BB +/BB + or below.
The Bloomberg Barclays 1-3 Month U.S. Treasury Bill Index tracks the performance of U.S. Treasury Bills with a remaining maturity of one to three months. U.S. Treasury Bills, which are short-term loans to the U.S. government, are full-faith-and-credit obligations of the U.S. Treasury and are generally regarded as being free of any risk of default.
Risks and Other Considerations
Investing involves risk, including the possible loss of principal and fluctuation of value.
The views expressed in this report reflect those of the portfolio managers only through the report period as stated on the cover. These views are expressed for informational purposes only and are subject to change at any time, based on market and other conditions, and may not come to pass. These views may differ from views of other investment professionals at Guggenheim and should not be construed as research, investment advice or a recommendation of any kind regarding the fund or any issuer or security, do not constitute a solicitation to buy or sell any security and should not be considered specific
 

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 9

 
   
QUESTIONS & ANSWERS (Unaudited) continued 
November 30, 2016 
 
legal, investment or tax advice. The information provided does not take into account the specific objectives, financial situation or particular needs of any specific investor.
The views expressed in this report may also include forward looking statements that involve risk and uncertainty, and there is no guarantee that any predictions will come to pass. Actual results or events may differ materially from those projected, estimated, assumed or anticipated in any such forward-looking statements. Important factors that could result in such differences, in addition to the other factors noted with such forward-looking statements, include general economic conditions such as inflation, recession and interest rates.
There can be no assurance that the Fund will achieve its investment objectives or that any investment strategies or techniques discussed herein will be effective. The value of the Fund will fluctuate with the value of the underlying securities. Historically, closed-end funds often trade at a discount to their net asset value.
Performance data quoted represents past performance, which is no guarantee of future results and current performance may be lower or higher than the figures shown.
Please see guggenheiminvestments.com/gof for a detailed discussion of the Fund’s risks and considerations.
 

10 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT

 
   
FUND SUMMARY (Unaudited) 
November 30, 2016 
 
 
Fund Statistics 
 
Share Price 
$19.22 
Net Asset Value 
$18.74 
Premium to NAV 
2.56% 
Net Assets ($000) 
$346,867 
 
           
AVERAGE ANNUAL TOTAL RETURNS FOR THE 
 
 
 
PERIOD ENDED NOVEMBER 30, 2016 
 
 
 
 
Six Month 
 
 
 
Since 
 
(non- 
One 
Three 
Five 
Inception 
 
annualized) 
Year 
Year 
Year 
(07/26/07) 
Guggenheim Strategic Opportunities Fund 
 
 
 
 
NAV 
13.58% 
17.15% 
9.12% 
11.72% 
11.28% 
Market 
15.76% 
22.90% 
8.06% 
10.15% 
11.19% 
 
Performance data quoted represents past performance, which is no guarantee of future results, and current performance may be lower or higher than the figures shown. All NAV returns include the deduction of management fees, operating expenses, and all other Fund expenses. The deduction of taxes that a shareholder would pay on Fund distributions or the sale of Fund shares is not reflected in the total returns. For the most recent month-end performance figures, please visit guggenheiminvestments.com/gof. The investment return and principal value of an investment will fluctuate with changes in market conditions and other factors so that an investor’s shares, when sold, may be worth more or less than their original cost.
Ten Largest Holdings 
     
(% of Total Net Assets) 
     
Airplanes Pass Through Trust, 1.09% due 03/15/2019 
   
1.1
%
Cosmopolitan Hotel Trust 2016, 5.18% due 11/15/2033 
   
1.0
%
Apollo Aviation Securitization Equity Trust, 7.37% due 12/15/2029 
   
1.0
%
Kenya Government International Bond, 6.88% due 06/24/2024 
   
1.0
%
QBE Insurance Group Ltd., 7.25% due 11/24/2043 
   
1.0
%
Ziggurat CLO Ltd., 5.88% due 10/17/2026 
   
1.0
%
GS Mortgage Securities Corporation Trust, 9.04% due 02/15/2033 
   
0.9
%
Flatiron CLO Ltd., 4.48% due 01/17/2026 
   
0.9
%
FDF II Ltd., 7.70% due 05/12/2031 
   
0.9
%
Anchorage Credit Funding 1 Ltd., 6.30% due 07/28/2030 
   
0.9
%
Top Ten Total 
   
9.7
%
“Ten Largest Holdings” excludes any temporary cash or derivative investments. 
       
 

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 11


   
FUND SUMMARY (Unaudited) continued 
November 30, 2016 





12 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
FUND SUMMARY (Unaudited) continued 
November 30, 2016 
 
 
 
Portfolio Breakdown 
 
% of Net Assets
Investments: 
     
Asset Backed Securities 
   
47.5
%
Corporate Bonds 
   
41.4
%
Senior Floating Rate Interests 
   
38.7
%
U.S. Government Securities 
   
7.0
%
Collateralized Mortgage Obligations 
   
3.7
%
Foreign Government Bonds 
   
2.0
%
Preferred Stocks 
   
0.8
%
Municipal Bonds 
   
0.6
%
Common Stocks 
   
0.5
%
Money Market Fund 
   
0.2
%
Warrants 
   
0.0
%*
Total Investments 
   
142.4
%
Call Options Written 
   
-0.2
%
Other Assets & Liabilities, net 
   
-42.2
%
Net Assets 
   
100.0
%
*Less than 0.1%
Holdings diversification and holdings are subject to change daily. For more information, please visit guggenheiminvestments.com/gof. The above summaries are provided for informational purposes only and should not be viewed as recommendations. Past performance does not guarantee future results.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 13


   
FUND SUMMARY (Unaudited) continued 
November 30, 2016 
 
 
Portfolio Composition by Quality Rating* 
 
 
 
% of Total 
Rating 
Investments 
Fixed Income Instruments 
 
AAA 
4.8% 
AA 
0.4% 
3.7% 
BBB 
12.9% 
BB 
16.4% 
32.2% 
CCC 
5.2% 
CC 
0.9% 
NR** 
11.8% 
Other Instruments 
 
Other 
0.2% 
Short Term Investments 
11.5% 
Total Investments 
100.0% 
 
Source: BlackRock Solutions. Credit quality ratings are measured on a scale that generally ranges from AAA (highest) to D (lowest). All securities except for “NR”, or not rated, have been rated by Moody’s, Standard & Poor’s (“S&P”), or Fitch, which are all a Nationally Recognized Statistical Rating Organization (“NRSRO”). For purposes of this presentation, when ratings are available from more than one agency, the highest rating is used. Guggenheim Investments has converted Moody’s and Fitch ratings to the equivalent S&P rating. Security ratings are determined at the time of purchase and may change thereafter. 
 
** 
NR securities do not necessarily indicate low credit quality. 
 

14 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) 
 
November 30, 2016 
 
 
 
 
 
 
Shares
   
Value
 
COMMON STOCKS– 0.5% 
           
Technology – 0.2% 
           
Aspect Software Parent, Inc.*,†††,1 
   
49,412
   
$
748,102
 
Qlik Technologies, Inc. A*,†††,1 
   
56
     
55,840
 
Qlik Technologies, Inc. B*,†††,1 
   
13,812
     
564
 
Qlik Technologies, Inc.*,†††,1 
   
3,600
     
 
Total Technology 
           
804,506
 
   
Energy – 0.2% 
               
SandRidge Energy, Inc.*,2 
   
18,206
     
416,918
 
Titan Energy LLC*,2 
   
9,603
     
220,869
 
Total Energy 
           
637,787
 
   
Communications – 0.1% 
               
Cengage Learning Acquisitions, Inc.*,†† 
   
11,126
     
209,536
 
   
Consumer, Non-cyclical – 0.0%** 
               
Targus Group International Equity, Inc*,†††,1 
   
13,409
     
19,577
 
   
Basic Materials – 0.0%** 
               
Mirabela Nickel Ltd.*,†††,1 
   
5,244,841
     
387
 
   
Consumer, Cyclical – 0.0%** 
               
Deb Stores Holding LLC*,†††,1 
   
9,389
     
1
 
   
Industrial – 0.0%** 
               
Carey International, Inc.*,†††,1 
   
5,666
     
1
 
Total Common Stocks 
               
(Cost $4,232,523) 
           
1,671,795
 
   
PREFERRED STOCKS– 0.8% 
               
Industrial – 0.6% 
               
Seaspan Corp. 
               
6.38%2
   
90,925
     
2,238,574
 
   
Financial – 0.2% 
               
AgriBank FCB 
               
6.88%2
   
4,000
     
432,250
 
Public Storage 
               
5.90%
   
10,000
     
249,500
 
Total Financial 
           
681,750
 
Total Preferred Stocks 
               
(Cost $2,921,804) 
           
2,920,324
 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 15

 
     
SCHEDULE OF INVESTMENTS (Unaudited) 
 
November 30, 2016 

   
 
 
Shares
   
Value
 
WARRANTS†† – 0.0%** 
           
Comstock Resources, Inc. 
           
expiring 09/06/181 
   
3,575
   
$
33,784
 
Total Warrants 
               
(Cost $13,658) 
           
33,784
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
SHORT TERM INVESTMENTS – 7.2% 
           
U.S. GOVERNMENT SECURITIES†† – 7.0% 
           
United States Treasury Bill 
           
0.00% due 12/08/162,3,14 
   
5,500,000
   
$
5,499,852
 
0.00% due 01/12/172,3 
   
5,100,000
     
5,098,139
 
0.00% due 01/26/172,3 
   
4,400,000
     
4,397,474
 
0.00% due 12/22/162,3 
   
4,300,000
     
4,299,385
 
0.00% due 01/19/172,3 
   
3,200,000
     
3,198,534
 
0.00% due 02/09/172,3 
   
1,200,000
     
1,198,981
 
0.00% due 12/29/163 
   
600,000
     
599,830
 
Total U.S. Government Securities 
               
(Cost $24,292,748) 
           
24,292,195
 
 
 
 
Shares
   
Value
 
MONEY MARKET FUND– 0.2% 
           
Dreyfus Treasury Prime Cash Management Fund - Investor Shares 
           
0.24%4
           
(Cost $472,490) 
   
472,490
   
$
472,490
 
Total Short Term Investments 
               
(Cost $24,765,238) 
           
24,764,685
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
ASSET BACKED SECURITIES†† – 47.5% 
           
Collateralized Loan Obligation – 36.2% 
           
Ziggurat CLO Ltd. 
           
2014-1A, 5.88% due 10/17/262,5,6 
   
4,000,000
   
$
3,325,136
 
Sound Point CLO III Ltd. 
               
2013-2A, 6.23% due 07/15/252,5,6 
   
2,875,000
     
2,212,048
 
2013-2A, 4.78% due 07/15/252,5,6 
   
1,000,000
     
989,932
 
KVK CLO Ltd. 
               
2014-2A, 5.63% due 07/15/265,6 
   
3,000,000
     
2,291,509
 
2013-1A, due 04/14/252,6,7 
   
2,300,000
     
850,505
 
Flatiron CLO Ltd. 
               
2013-1A, 4.48% due 01/17/262,5,6 
   
3,300,000
     
3,083,677
 
ACAS CLO Ltd. 
               
2014-1A, 6.78% due 07/18/265,6 
   
3,750,000
     
2,929,116
 
 
See notes to financial statements.

16 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2016 
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
ASSET BACKED SECURITIES†† – 47.5% (continued) 
           
Collateralized Loan Obligation – 36.2% (continued) 
           
Great Lakes CLO Ltd. 
           
2015-1A, 4.63% due 07/15/265,6 
   
1,500,000
   
$
1,436,120
 
2012-1A, due 01/15/232,6,7 
   
2,500,000
     
1,017,032
 
2014-1A, 5.08% due 04/15/255,6 
   
500,000
     
456,493
 
Catamaran CLO Ltd. 
               
2014-1A, 5.38% due 04/20/265,6 
   
2,000,000
     
1,640,035
 
2014-1A, 6.63% due 04/20/262,5,6 
   
1,600,000
     
1,152,766
 
Venture XVI CLO Ltd. 
               
2014-16A, 4.33% due 04/15/262,5,6 
   
3,000,000
     
2,783,456
 
Fortress Credit Funding V, LP 
               
2015-5A, 6.31% due 08/15/222,5,6 
   
3,000,000
     
2,736,729
 
WhiteHorse VI Ltd. 
               
2013-1A, 6.13% due 02/03/252,5,6 
   
1,750,000
     
1,478,681
 
2013-1A, 7.38% due 02/03/252,5,6 
   
2,000,000
     
1,257,004
 
THL Credit Wind River CLO Ltd. 
               
2015-2A, 8.68% due 10/15/275,6 
   
3,000,000
     
2,673,202
 
Flagship CLO VIII Ltd. 
               
2014-8A, 6.08% due 01/16/265,6 
   
3,250,000
     
2,673,191
 
Newstar Trust 
               
2012-2I, 7.45% due 01/20/235 
   
3,000,000
     
2,673,036
 
Eaton Vance CLO 2015-1 Ltd. 
               
2015-1A, 8.93% due 10/20/265,6 
   
3,000,000
     
2,651,149
 
Saranac CLO II Ltd. 
               
2014-2A, 6.06% due 02/20/255,6 
   
3,000,000
     
2,437,859
 
Denali Capital CLO X Ltd. 
               
2013-1A, 6.63% due 04/28/255,6 
   
3,000,000
     
2,421,441
 
Fortress Credit Opportunities 
               
2005-1A, 0.96% due 07/15/192,5,8 
   
2,447,366
     
2,355,560
 
AMMC CLO XII Ltd. 
               
2013-12A, 5.93% due 05/10/255,6 
   
3,000,000
     
2,328,285
 
Octagon Investment Partners XVI Ltd. 
               
2013-1A, 6.38% due 07/17/255,6 
   
3,000,000
     
2,213,842
 
Carlyle Global Market Strategies CLO Ltd. 
               
2012-3A, due 10/04/246,7 
   
2,600,000
     
2,133,195
 
Jamestown CLO III Ltd. 
               
2013-3A, 4.18% due 01/15/262,5,6 
   
2,250,000
     
2,068,119
 
Voya CLO Ltd. 
               
2013-1A, 4.38% due 04/15/242,5,6 
   
2,000,000
     
1,961,208
 
Avery 
               
2013-3X COM, due 01/18/257 
   
2,399,940
     
1,917,992
 
Dryden 30 Senior Loan Fund 
               
2013-30A, 6.40% due 11/15/252,5,6 
   
2,500,000
     
1,901,453
 
Fortress Credit Opportunities VI CLO Ltd. 
               
2015-6A, 5.85% due 10/10/262,5,6 
   
2,000,000
     
1,869,180
 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 17


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2016 
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
ASSET BACKED SECURITIES†† – 47.5% (continued) 
           
Collateralized Loan Obligation – 36.2% (continued) 
           
Golub Capital Partners CLO 24M Ltd. 
           
2015-24A, 5.13% due 02/05/272,5,6 
   
2,000,000
   
$
1,830,141
 
Shackleton IV CLO Ltd. 
               
2013-4A, 6.63% due 01/13/255,6 
   
2,350,000
     
1,789,363
 
OHA Credit Partners IX Ltd. 
               
2013-9A, due 10/20/252,6,7 
   
2,000,000
     
1,757,153
 
Treman Park CLO Ltd. 
               
2015-1A, due 04/20/272,6,7 
   
2,000,000
     
1,753,857
 
OCP CLO Ltd. 
               
2015-9A, 7.28% due 07/15/275,6 
   
2,250,000
     
1,742,677
 
Mountain View CLO Ltd. 
               
2015-9A, 6.23% due 07/15/275,6 
   
2,000,000
     
1,725,306
 
Steele Creek CLO Ltd. 
               
2015-1A, 6.16% due 02/21/272,5,6 
   
2,000,000
     
1,700,089
 
Cent CLO 19 Ltd. 
               
2013-19A, 4.19% due 10/29/252,5,6 
   
1,750,000
     
1,653,874
 
Monroe Capital CLO Ltd. 
               
2014-1A, 5.61% due 10/22/262,5,6 
   
1,750,000
     
1,645,036
 
Ares XXVI CLO Ltd. 
               
2013-1A, due 04/15/256,7 
   
3,700,000
     
1,641,480
 
CIFC Funding V Ltd. 
               
2014-5A, 7.43% due 01/17/275,6 
   
2,000,000
     
1,633,156
 
Ares XXXIII CLO Ltd. 
               
2015-1A, 7.34% due 12/05/255,6 
   
2,000,000
     
1,596,017
 
Voya CLO Ltd. 
               
2014-4A, 6.88% due 10/14/265,6 
   
1,950,000
     
1,549,295
 
Race Point VII CLO Ltd. 
               
2012-7A, 5.13% due 11/08/242,5,6 
   
1,500,000
     
1,499,806
 
Mountain Hawk II CLO Ltd. 
               
2013-2A, 4.03% due 07/22/242,5,6 
   
1,750,000
     
1,463,801
 
Fortress Credit Opportunities V CLO Ltd. 
               
2014-5A, 5.78% due 10/15/262,5,6 
   
1,500,000
     
1,442,509
 
Babson CLO Limited 
               
2015-2A, 7.63% due 07/20/275,6 
   
1,750,000
     
1,434,621
 
Atlas Senior Loan Fund II Ltd. 
               
2012-2A, due 01/30/242,6,7 
   
2,600,000
     
1,401,060
 
CIFC Funding Ltd. 
               
2012-1X, 8.72% due 08/14/24 
   
1,150,000
     
967,809
 
2014-3A, 5.63% due 07/22/262,5,6 
   
500,000
     
428,497
 
Cent CLO 22 Ltd. 
               
2014-22A, 7.28% due 11/07/265,6 
   
1,750,000
     
1,335,019
 
Avery Point III CLO Ltd. 
               
2013-3A, 5.88% due 01/18/252,5,6 
   
1,500,000
     
1,272,750
 
Regatta IV Funding Ltd. 
               
2014-1A, 5.83% due 07/25/265,6 
   
1,500,000
     
1,232,925
 
 
See notes to financial statements.

18 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2016 
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
ASSET BACKED SECURITIES†† – 47.5% (continued) 
           
Collateralized Loan Obligation – 36.2% (continued) 
           
Finn Square CLO Ltd. 
           
2012-1A, due 12/24/236,7 
   
2,500,000
   
$
1,217,648
 
Neuberger Berman CLO Ltd. 
               
2012-12A, due 07/25/236,7 
   
2,500,000
     
1,204,223
 
NewStar Arlington Senior Loan Program LLC 
               
2014-1A, 5.13% due 07/25/252,5,6 
   
750,000
     
693,359
 
2014-1A, 5.97% due 07/25/252,6 
   
500,000
     
501,650
 
Babson CLO Ltd. 
               
2012-2A, due 05/15/236,7 
   
2,000,000
     
1,166,477
 
CIFC Funding 2014-IV Ltd. 
               
2014-4A, 6.48% due 10/17/265,6 
   
1,500,000
     
1,162,629
 
Madison Park Funding XI Ltd. 
               
2013-11A, 6.03% due 10/23/255,6 
   
1,500,000
     
1,156,219
 
OCP CLO Ltd. 
               
2013-4A, 5.88% due 10/24/255,6 
   
1,250,000
     
1,040,086
 
Avery Point IV CLO Ltd. 
               
2014-1A, 5.88% due 04/25/262,5,6 
   
1,430,000
     
1,031,519
 
Sound Point CLO I Ltd. 
               
2012-1A, 5.46% due 10/20/232,5,6 
   
1,000,000
     
1,000,368
 
Cent CLO 16, LP 
               
2014-16A, 5.14% due 08/01/242,5,6 
   
1,000,000
     
1,000,122
 
Voya CLO Ltd. 
               
2015-3A, 4.83% due 10/15/222,5,6 
   
1,000,000
     
997,872
 
Cerberus Onshore II CLO-2 LLC 
               
2014-1A, 5.03% due 10/15/232,5,6 
   
1,000,000
     
989,031
 
Garrison Funding Ltd. 
               
2016-2A, 4.62% due 09/29/27†††,2,5,6 
   
1,000,000
     
985,660
 
Kingsland VI Ltd. 
               
2013-6A, 4.54% due 10/28/245,6 
   
1,000,000
     
956,332
 
Golub Capital Partners CLO 25M Ltd. 
               
2015-25A, 4.53% due 08/05/272,5,6 
   
1,000,000
     
954,706
 
Fortress Credit Opportunities III CLO, LP 
               
2014-3A, 4.12% due 04/28/262,5,6 
   
1,000,000
     
947,495
 
Atlas Senior Loan Fund IV Ltd. 
               
2014-2A, 4.36% due 02/17/262,5,6 
   
1,000,000
     
923,217
 
Ares XXV CLO Ltd. 
               
2013-3A, due 01/17/246,7 
   
1,750,000
     
904,957
 
Venture XIII CLO Ltd. 
               
2013-13A, due 06/10/256,7 
   
1,500,000
     
902,933
 
Dryden 37 Senior Loan Fund 
               
2015-37A, due 04/15/276,7 
   
1,050,000
     
880,114
 
Keuka Park CLO Ltd. 
               
2013-1A, due 10/21/242,6,7 
   
1,500,000
     
769,365
 
OCP CLO 2015-8 Ltd. 
               
2015-8A, 6.88% due 04/17/275,6 
   
1,000,000
     
739,045
 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 19


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2016 
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
ASSET BACKED SECURITIES†† – 47.5% (continued) 
           
Collateralized Loan Obligation – 36.2% (continued) 
           
Resource Capital Corporation 
           
2014-CRE2, 3.05% due 04/15/322,5,6 
   
729,000
   
$
705,038
 
Newstar Commercial Loan Funding LLC 
               
2014-1A, 5.63% due 04/20/252,5,6 
   
500,000
     
475,068
 
2013-1A, 6.16% due 09/20/235,6 
   
250,000
     
226,799
 
Marathon CLO Ltd. 
               
due 02/21/257 
   
1,300,000
     
690,698
 
Octagon Loan Funding Ltd. 
               
2014-1A, 6.11% due 11/18/262,5,6 
   
700,000
     
626,368
 
West CLO Ltd. 
               
2013-1A, due 11/07/256,7 
   
1,350,000
     
536,998
 
COA Summit CLO Limited 
               
2014-1A, 4.73% due 04/20/232,5,6 
   
500,000
     
493,018
 
NXT Capital CLO LLC 
               
2013-1A, 5.03% due 04/25/242,5,6 
   
500,000
     
476,203
 
MCF CLO IV LLC 
               
2014-1A, 6.78% due 10/15/252,5,6 
   
500,000
     
430,820
 
Golub Capital Partners CLO Ltd. 
               
2014-18A, 4.88% due 04/25/262,5,6 
   
300,000
     
270,676
 
Marathon CLO II Ltd. 
               
2005-2A, due 12/20/19†††,1,5,6,7 
   
3,000,000
     
3
 
Total Collateralized Loan Obligation 
           
125,471,908
 
Transportation – 6.0% 
               
Apollo Aviation Securitization Equity Trust 
               
2014-1, 7.37% due 12/15/295 
   
3,410,256
     
3,384,679
 
2014-1, 5.13% due 12/15/295 
   
1,705,128
     
1,692,340
 
Airplanes Pass Through Trust 
               
2001-1A, 1.09% due 03/15/195,8 
   
12,068,641
     
3,922,308
 
Apollo Aviation Securitization Equity Trust 
               
2016-1A, 9.20% due 03/17/362,6,9 
   
2,600,100
     
2,639,102
 
2016-2, 7.87% due 11/15/416 
   
2,500,000
     
2,501,185
 
2016-2, 5.93% due 11/15/416 
   
1,000,000
     
999,949
 
ECAF I Ltd. 
               
2015-1A, 5.80% due 06/15/406 
   
2,519,634
     
2,538,531
 
Stripes 
               
2013-1 A1, 4.06% due 03/20/23††† 
   
1,728,319
     
1,684,848
 
Turbine Engines Securitization Ltd. 
               
2013-1A, 6.38% due 12/13/488 
   
701,105
     
652,729
 
Rise Ltd. 
               
2014-1AB, 6.50% due 02/12/39††† 
   
416,667
     
407,098
 
BBAM Acquisition Finance 
               
5.38% due 09/17/18 
   
277,492
     
276,104
 
Total Transportation 
           
20,698,873
 
 
See notes to financial statements.

20 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2016 
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
ASSET BACKED SECURITIES†† – 47.5% (continued) 
           
Collateralized Debt Obligation – 3.8% 
           
FDF II Ltd. 
           
2016-2A, 7.70% due 05/12/312,6 
   
3,000,000
   
$
3,025,353
 
Anchorage Credit Funding 1 Ltd. 
               
2015-1A, 6.30% due 07/28/302,8 
   
3,000,000
     
3,008,599
 
FDF I Ltd. 
               
2015-1A, 6.88% due 11/12/302,6 
   
2,000,000
     
2,000,784
 
2015-1A, 7.50% due 11/12/302,6 
   
1,000,000
     
1,006,641
 
SRERS Funding Ltd. 
               
2011-RS, 0.79% due 05/09/465,6 
   
2,545,974
     
2,495,362
 
Anchorage Credit Funding 4 Ltd. 
               
2016-4A, 5.50% due 02/15/356 
   
1,000,000
     
959,580
 
Highland Park CDO I Ltd. 
               
2006-1A, 1.33% due 11/25/512,5,6 
   
827,394
     
763,271
 
Total Collateralized Debt Obligation 
           
13,259,590
 
Other – 0.7% 
               
Emerald Aviation Finance Ltd. 
               
2013-1, 6.35% due 10/15/382,6,9 
   
1,287,105
     
1,304,802
 
Glenn Pool Oil & Gas Trust 
               
6.00% due 08/02/21††† 
   
1,035,382
     
983,396
 
Total Other 
           
2,288,198
 
Financial – 0.4% 
               
NCBJ 2015-1 A 
               
5.88% due 07/08/22†††,1 
   
1,500,000
     
1,500,000
 
Aircraft – 0.3% 
               
Castlelake Aircraft Securitization Trust 
               
2014-1, 7.50% due 02/15/29 
   
1,251,454
     
1,248,951
 
Credit Cards – 0.1% 
               
Credit Card Pass-Through Trust 
               
2012-BIZ, 0.00% due 12/15/496 
   
294,396
     
232,284
 
Total Asset Backed Securities 
               
(Cost $171,999,901) 
           
164,699,804
 
CORPORATE BONDS†† – 41.4% 
               
Financial – 14.4% 
               
Citigroup, Inc. 
               
5.95%2,10,11 
   
3,000,000
     
2,947,500
 
5.88%2,10,11 
   
1,000,000
     
1,000,000
 
Bank of America Corp. 
               
6.50%2,10,11 
   
2,000,000
     
2,081,400
 
6.10%2,10,11 
   
1,750,000
     
1,750,000
 
QBE Insurance Group Ltd. 
               
7.25% due 11/24/435,6 
   
3,000,000
     
3,360,000
 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 21


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2016 
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
CORPORATE BONDS†† – 41.4% (continued) 
           
Financial – 14.4% (continued) 
           
Jefferies Finance LLC / JFIN Company-Issuer Corp. 
           
7.50% due 04/15/212,6 
   
2,150,000
   
$
2,090,875
 
7.38% due 04/01/202,6 
   
950,000
     
928,625
 
GMH Military Housing-Navy Northeast LLC 
               
6.30% due 10/15/49†††,2 
   
2,900,000
     
2,709,908
 
GEO Group, Inc. 
               
6.00% due 04/15/262 
   
2,000,000
     
1,920,000
 
5.88% due 10/15/242 
   
600,000
     
579,000
 
5.88% due 01/15/22 
   
100,000
     
99,750
 
Customers Bank 
               
6.13% due 06/26/295,8 
   
2,500,000
     
2,525,000
 
Citizens Financial Group, Inc. 
               
5.50%2,10,11
   
2,500,000
     
2,425,000
 
Fifth Third Bancorp 
               
4.90%2,10,11
   
1,500,000
     
1,402,500
 
5.10%2,10,11
   
815,000
     
764,063
 
NewStar Financial, Inc. 
               
7.25% due 05/01/202 
   
2,100,000
     
2,084,250
 
NFP Corp. 
               
9.00% due 07/15/212,6 
   
1,950,000
     
2,018,250
 
Fort Knox Military Housing Privatization Project 
               
5.82% due 02/15/526 
   
1,972,568
     
1,964,402
 
CNB Financial Corp. 
               
5.75% due 10/15/26†††,5,6 
   
2,000,000
     
1,962,277
 
Atlas Mara Ltd. 
               
8.00% due 12/31/20 
   
2,200,000
     
1,848,000
 
FBM Finance, Inc. 
               
8.25% due 08/15/212,6 
   
1,750,000
     
1,811,250
 
Garfunkelux Holding Co. 3 S.A. 
               
8.50% due 11/01/22 
 
1,400,000 GBP
     
1,808,646
 
AmTrust Financial Services, Inc. 
               
6.13% due 08/15/232 
   
1,654,000
     
1,678,132
 
Greystar Real Estate Partners LLC 
               
8.25% due 12/01/222,6 
   
1,450,000
     
1,569,625
 
Cadence Bank North America 
               
6.25% due 06/28/292,5,6 
   
1,600,000
     
1,400,000
 
Fidelity & Guaranty Life Holdings, Inc. 
               
6.38% due 04/01/212,6 
   
1,065,000
     
1,054,350
 
HUB International Ltd. 
               
9.25% due 02/15/212,6 
   
1,000,000
     
1,030,000
 
Lincoln Finance Ltd. 
               
7.38% due 04/15/212,6 
   
800,000
     
856,000
 
Pacific Beacon LLC 
               
5.63% due 07/15/512,8 
   
715,735
     
666,964
 
 
See notes to financial statements.

22 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2016 
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
CORPORATE BONDS†† – 41.4% (continued) 
           
Financial – 14.4% (continued) 
           
Atlantic Marine Corporations Communities LLC 
           
5.38% due 02/15/482 
   
553,257
   
$
510,258
 
Icahn Enterprises Limited Partnership / Icahn Enterprises Finance Corp. 
               
6.00% due 08/01/202 
   
300,000
     
298,659
 
5.88% due 02/01/22 
   
200,000
     
192,500
 
Jefferies LoanCore LLC / JLC Finance Corp. 
               
6.88% due 06/01/202,6 
   
500,000
     
473,750
 
Total Financial 
           
49,810,934
 
Consumer, Cyclical – 4.5% 
               
Ferrellgas Limited Partnership / Ferrellgas Finance Corp. 
               
6.75% due 06/15/232 
   
2,335,000
     
2,171,549
 
6.50% due 05/01/21 
   
429,000
     
405,405
 
WMG Acquisition Corp. 
               
6.75% due 04/15/222,6 
   
2,130,000
     
2,231,174
 
NPC International Incorporated / NPC Operating Company A Inc / 
               
NPC Operating Company B Inc. 10.50% due 01/15/202 
   
2,055,000
     
2,125,899
 
HP Communities LLC 
               
6.82% due 09/15/532,8 
   
978,261
     
1,054,859
 
6.16% due 09/15/53†††,2,8 
   
1,000,000
     
993,878
 
Nathan’s Famous, Inc. 
               
10.00% due 03/15/202,6 
   
1,804,000
     
1,966,359
 
TVL Finance plc 
               
8.50% due 05/15/23 
 
1,300,000 GBP
     
1,707,021
 
Exide Technologies 
               
11.00% due 04/30/202,12 
   
2,068,358
     
1,649,516
 
PF Chang’s China Bistro, Inc. 
               
10.25% due 06/30/202,6 
   
1,255,000
     
1,195,388
 
Total Consumer, Cyclical 
           
15,501,048
 
Energy – 4.2% 
               
Keane Group Holdings LLC 
               
12.00% due 08/08/19†††,1 
   
1,900,000
     
1,743,250
 
Husky Energy, Inc. 
               
4.00% due 04/15/242 
   
900,000
     
914,300
 
3.95% due 04/15/222 
   
600,000
     
622,988
 
Comstock Resources, Inc. 
               
10.00% due 03/15/202,12 
   
1,300,000
     
1,280,499
 
Halcon Resources Corp. 
               
8.63% due 02/01/202,6 
   
1,100,000
     
1,128,050
 
TerraForm Power Operating LLC 
               
6.38% due 02/01/232,6,9 
   
1,096,000
     
1,120,989
 
Hess Corp. 
               
8.13% due 02/15/192 
   
950,000
     
1,062,687
 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 23


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2016 
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
CORPORATE BONDS†† – 41.4% (continued) 
           
Energy – 4.2% (continued) 
           
Sunoco Logistics Partners Operations, LP 
           
4.25% due 04/01/242 
   
1,000,000
   
$
998,836
 
Approach Resources, Inc. 
               
7.00% due 06/15/212 
   
1,034,000
     
904,750
 
EQT Corp. 
               
8.13% due 06/01/192 
   
800,000
     
901,366
 
CONSOL Energy, Inc. 
               
8.00% due 04/01/232 
   
850,000
     
867,000
 
Buckeye Partners, LP 
               
4.35% due 10/15/242 
   
750,000
     
758,620
 
Crestwood Midstream Partners Limited Partnership / Crestwood Midstream Finance Corp. 
               
6.25% due 04/01/232 
   
400,000
     
406,000
 
6.13% due 03/01/222 
   
200,000
     
202,000
 
Gibson Energy, Inc. 
               
6.75% due 07/15/212,6 
   
550,000
     
570,625
 
SandRidge Energy, Inc. 
               
0.00% due 10/04/202,3 
   
429,218
     
522,305
 
QEP Resources, Inc. 
               
6.88% due 03/01/212 
   
350,000
     
360,500
 
Schahin II Finance Company SPV Ltd. 
               
5.88% due 09/25/222,8,13 
   
1,216,133
     
145,936
 
SandRidge Energy, Inc. Escrow Notes 
               
8.75% due 06/01/182,6,13 
   
1,900,000
     
190
 
Total Energy 
           
14,510,891
 
Communications – 4.0% 
               
DISH DBS Corp. 
               
5.88% due 11/15/242 
   
2,050,000
     
2,078,188
 
7.75% due 07/01/262 
   
1,075,000
     
1,186,531
 
MDC Partners, Inc. 
               
6.50% due 05/01/242,6 
   
2,900,000
     
2,490,375
 
SFR Group S.A. 
               
7.38% due 05/01/262,6 
   
1,800,000
     
1,795,500
 
Inmarsat Finance plc 
               
6.75% due 05/15/222,6 
   
1,850,000
     
1,762,125
 
Midcontinent Communications / Midcontinent Finance Corp. 
               
6.88% due 08/15/232,6 
   
1,300,000
     
1,366,625
 
Sprint Communications, Inc. 
               
7.00% due 03/01/202,6 
   
800,000
     
860,496
 
EIG Investors Corp. 
               
10.88% due 02/01/242,8 
   
750,000
     
697,500
 
McGraw-Hill Global Education Holdings LLC / McGraw-Hill Global Education Finance 
               
7.88% due 05/15/242,6 
   
550,000
     
541,750
 
CSC Holdings LLC 
               
6.75% due 11/15/212 
   
500,000
     
525,625
 
 
See notes to financial statements.

24 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2016 
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
CORPORATE BONDS†† – 41.4% (continued) 
           
Communications – 4.0% (continued) 
           
Zayo Group LLC / Zayo Capital, Inc. 
           
6.38% due 05/15/252 
   
400,000
   
$
416,000
 
Interoute Finco plc 
               
4.63% due 10/12/22 
 
295,000 EUR
     
335,673
 
Total Communications 
           
14,056,388
 
Consumer, Non-cyclical – 4.0% 
               
Bumble Bee Holdings, Inc. 
               
9.00% due 12/15/172,6 
   
2,082,000
     
2,055,975
 
Kinetic Concepts Incorporated / KCI USA Inc 
               
7.88% due 02/15/212,6 
   
1,691,000
     
1,784,005
 
Tenet Healthcare Corp. 
               
7.50% due 01/01/226 
   
1,700,000
     
1,747,812
 
Halyard Health, Inc. 
               
6.25% due 10/15/222 
   
1,600,000
     
1,636,000
 
Midas Intermediate Holdco II LLC / Midas Intermediate Holdco II Finance, Inc. 
               
7.88% due 10/01/222,6 
   
1,625,000
     
1,633,125
 
Albertsons Companies LLC / Safeway Incorporated / New Albertson’s Inc / Albertson’s LLC 
               
6.63% due 06/15/242,6 
   
1,500,000
     
1,550,400
 
Bumble Bee Holdco SCA 
               
9.63% due 03/15/182,6,12 
   
1,400,000
     
1,372,000
 
Acadia Healthcare Company, Inc. 
               
5.63% due 02/15/232 
   
1,000,000
     
985,000
 
6.50% due 03/01/24 
   
250,000
     
248,750
 
KeHE Distributors LLC / KeHE Finance Corp. 
               
7.63% due 08/15/212,6 
   
550,000
     
547,250
 
Opal Acquisition, Inc. 
               
8.88% due 12/15/212,6 
   
255,000
     
199,538
 
Total Consumer, Non-cyclical 
           
13,759,855
 
Industrial – 3.6% 
               
Summit Materials LLC / Summit Materials Finance Corp. 
               
8.50% due 04/15/222 
   
2,150,000
     
2,367,687
 
StandardAero Aviation Holdings, Inc. 
               
10.00% due 07/15/232,6 
   
2,025,000
     
2,138,906
 
Princess Juliana International Airport Operating Company N.V. 
               
5.50% due 12/20/27†††,2,6 
   
1,846,953
     
1,865,423
 
Dynagas LNG Partners Limited Partnership / Dynagas Finance, Inc. 
               
6.25% due 10/30/192 
   
1,800,000
     
1,707,750
 
Novelis Corp. 
               
5.88% due 09/30/262,6 
   
1,600,000
     
1,598,000
 
LMI Aerospace, Inc. 
               
7.38% due 07/15/192 
   
1,575,000
     
1,571,063
 
Coveris Holdings S.A. 
               
7.88% due 11/01/192,6 
   
930,000
     
913,725
 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 25


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2016 
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
CORPORATE BONDS†† – 41.4% (continued) 
           
Industrial – 3.6% (continued) 
           
Ardagh Packaging Finance plc / Ardagh Holdings USA, Inc. 
           
7.25% due 05/15/242,6 
   
250,000
   
$
261,250
 
Total Industrial 
           
12,423,804
 
Basic Materials – 3.5% 
               
BHP Billiton Finance USA Ltd. 
               
6.75% due 10/19/752,5,6 
   
2,000,000
     
2,205,000
 
Yamana Gold, Inc. 
               
4.95% due 07/15/242 
   
2,160,000
     
2,117,653
 
Eldorado Gold Corp. 
               
6.13% due 12/15/202,6 
   
1,950,000
     
1,964,625
 
Alcoa Nederland Holding BV 
               
7.00% due 09/30/262,6 
   
1,650,000
     
1,749,000
 
GCP Applied Technologies, Inc. 
               
9.50% due 02/01/232,6 
   
1,475,000
     
1,670,438
 
Constellium N.V. 
               
7.88% due 04/01/212,6 
   
1,288,000
     
1,384,600
 
Novelis, Inc. 
               
8.38% due 12/15/172 
   
877,000
     
880,289
 
Mirabela Nickel Ltd. 
               
2.38% due 06/24/19†††,1 
   
1,388,176
     
256,021
 
1.00% due 09/10/44†††,1 
   
27,743
     
 
Total Basic Materials 
           
12,227,626
 
Technology – 1.8% 
               
Micron Technology, Inc. 
               
7.50% due 09/15/232,6 
   
1,550,000
     
1,712,750
 
5.25% due 08/01/232,6 
   
200,000
     
197,500
 
Cengage Learning, Inc. 
               
9.50% due 06/15/242,6 
   
1,900,000
     
1,657,750
 
Infor US, Inc. 
               
6.50% due 05/15/222 
   
1,532,000
     
1,574,130
 
First Data Corp. 
               
7.00% due 12/01/232,6 
   
500,000
     
523,440
 
Epicor Software 
               
9.25% due 06/21/23†††,1 
   
500,000
     
488,500
 
CDK Global, Inc. 
               
5.00% due 10/15/24 
   
150,000
     
146,709
 
Total Technology 
           
6,300,779
 
Utilities – 1.4% 
               
LBC Tank Terminals Holding Netherlands BV 
               
6.88% due 05/15/232,6 
   
1,425,000
     
1,425,000
 
AES Corp. 
               
6.00% due 05/15/26 
   
1,400,000
     
1,375,500
 
 
See notes to financial statements.

26 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2016 
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
CORPORATE BONDS†† – 41.4% (continued) 
           
Utilities – 1.4% (continued) 
           
Terraform Global Operating LLC 
           
9.75% due 08/15/222,6 
   
1,150,000
   
$
1,227,625
 
AmeriGas Partners Limited Partnership / AmeriGas Finance Corp. 
               
5.88% due 08/20/262 
   
1,000,000
     
994,690
 
Total Utilities 
           
5,022,815
 
Total Corporate Bonds 
               
(Cost $140,963,913) 
           
143,614,140
 
SENIOR FLOATING RATE INTERESTS††,5 – 38.7% 
               
Consumer, Non-cyclical – 8.5% 
               
Reddy Ice Holdings, Inc. 
               
6.75% due 05/01/19 
   
2,271,899
     
2,142,696
 
American Seafoods Group LLC / American Seafoods Finance, Inc. 
               
6.02% due 08/19/21 
   
2,119,765
     
2,098,566
 
Copernicus Group, Inc. 
               
6.00% due 08/15/22 
   
2,000,000
     
2,000,000
 
AT Home Holding III 
               
5.00% due 06/03/22 
   
1,970,000
     
1,965,075
 
Pelican Products, Inc. 
               
5.25% due 04/10/20 
   
1,784,233
     
1,770,851
 
Give and Go Prepared Foods Corp. 
               
6.50% due 07/29/23 
   
1,650,000
     
1,647,938
 
Chef’s Warehouse Parent LLC 
               
6.75% due 06/22/22 
   
1,633,150
     
1,622,256
 
Bauer Performance Sports 
               
7.50% due 04/15/21 
   
1,575,000
     
1,559,644
 
American Academy Holdings 
               
6.25% due 05/17/21†††,1 
   
1,534,605
     
1,520,914
 
Arctic Glacier Holdings, Inc. 
               
6.00% due 05/10/19 
   
1,353,622
     
1,340,086
 
IHC Holding Corp. 
               
7.00% due 04/30/21†††,1 
   
987,500
     
976,602
 
7.25% due 04/30/21†††,1 
   
189,525
     
186,939
 
Hanger, Inc. 
               
11.50% due 08/01/19 
   
1,000,000
     
995,000
 
Affordable Care Holding 
               
5.75% due 10/24/22 
   
992,500
     
992,500
 
CPM Holdings 
               
6.00% due 04/11/22 
   
987,500
     
992,438
 
Sho Holding I Corp. 
               
6.00% due 10/27/22 
   
992,500
     
987,538
 
CTI Foods Holding Co. LLC 
               
8.25% due 06/28/21 
   
1,105,000
     
983,450
 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 27


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2016 
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
SENIOR FLOATING RATE INTERESTS††,5 – 38.7% (continued) 
           
Consumer, Non-cyclical – 8.5% (continued) 
           
Springs Industries, Inc. 
           
7.50% due 06/01/21†††,1 
   
997,500
   
$
977,083
 
ABB Concise Optical Group LLC 
               
6.00% due 06/15/23 
   
970,000
     
976,063
 
Lineage Logistics LLC 
               
4.50% due 04/07/21 
   
942,749
     
928,607
 
ABG Intermediate Holdings 2 LLC 
               
5.50% due 05/27/21 
   
913,926
     
911,641
 
American Tire Distributors, Inc. 
               
5.25% due 09/01/21 
   
700,000
     
688,044
 
Parts Town 
               
7.50% due 06/23/22††† 
   
650,000
     
650,000
 
NES Global Talent 
               
6.50% due 10/03/19 
   
322,958
     
290,662
 
Packaging Coordinators Midco, Inc. 
               
1.07% due 07/01/21†††,1 
   
115,385
     
101,412
 
Rite Aid Corp. 
               
5.75% due 08/21/20 
   
100,000
     
100,313
 
Targus Group International, Inc. 
               
15.00% due 12/31/19†††,1 
   
56,934
     
79,612
 
15.00% due 12/31/19†††,1 
   
2,693
     
3,765
 
14.00% due 05/24/16†††,1 
   
155,450
     
 
Total Consumer, Non-cyclical 
           
29,489,695
 
Technology – 8.0% 
               
Greenway Medical Technologies 
               
6.00% due 11/04/20 
   
1,691,553
     
1,649,264
 
9.25% due 11/04/21 
   
1,000,000
     
950,000
 
TIBCO Software, Inc. 
               
6.50% due 12/04/20 
   
2,408,356
     
2,401,132
 
Epicor Software 
               
4.75% due 06/01/22 
   
1,749,747
     
1,744,936
 
5.00% due 06/01/22 
   
500,000
     
501,875
 
Insight Venture 
               
7.25% due 07/15/21†††,1 
 
1,650,000 GBP
     
2,037,531
 
Infoblox, Inc. 
               
6.00% due 11/07/23 
   
2,000,000
     
1,964,160
 
EIG Investors Corp. 
               
6.00% due 02/09/23 
   
1,882,915
     
1,831,134
 
PowerSchool, Inc. 
               
5.88% due 07/30/21†††,1 
   
990,000
     
990,000
 
6.00% due 07/30/21†††,1 
   
583,590
     
583,590
 
6.38% due 07/30/21†††,1 
   
250,000
     
250,000
 
Project Alpha Intermediate Holding, Inc. 
               
9.25% due 08/22/22†††,1 
   
1,650,000
     
1,619,501
 
 
See notes to financial statements.

28 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2016 
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
SENIOR FLOATING RATE INTERESTS††,5 – 38.7% (continued) 
           
Technology – 8.0% (continued) 
           
Aspect Software, Inc. 
           
11.28% due 05/25/20 
   
917,785
   
$
905,551
 
10.85% due 05/25/18†††,1 
   
604,167
     
590,734
 
Solera LLC 
               
3.66% due 03/03/21†††,1 
   
1,287,567
     
1,133,437
 
Advanced Computer Software 
               
10.50% due 01/31/23 
   
1,250,000
     
1,121,875
 
Kronos, Inc. 
               
5.00% due 11/01/23 
   
1,000,000
     
1,002,190
 
MRI Software LLC 
               
5.25% due 06/23/21 
   
958,807
     
953,418
 
Sparta Holding Corp. 
               
6.50% due 07/28/20†††,1 
   
955,057
     
949,236
 
CPI Acquisition, Inc. 
               
5.50% due 08/17/22 
   
991,782
     
900,042
 
Touchtunes Interactive 
               
5.75% due 05/28/21 
   
888,750
     
886,528
 
Micron Technology, Inc. 
               
4.36% due 04/26/22 
   
822,938
     
831,611
 
GlobalLogic Holdings, Inc. 
               
6.25% due 06/02/19 
   
613,968
     
613,201
 
Landslide Holdings, Inc. 
               
5.50% due 09/27/22 
   
600,000
     
603,000
 
Active Network, Inc. 
               
5.50% due 11/13/20 
   
444,835
     
440,448
 
Ceridian Corp. 
               
4.50% due 09/15/20 
   
240,697
     
236,586
 
Total Technology 
           
27,690,980
 
Consumer, Cyclical – 7.1% 
               
Sears Holdings Corp. 
               
5.50% due 06/30/18 
   
2,557,566
     
2,493,628
 
Navistar, Inc. 
               
6.50% due 08/07/20 
   
2,376,992
     
2,394,083
 
Belk, Inc. 
               
5.75% due 12/12/22 
   
2,530,875
     
2,249,315
 
K & N Parent, Inc. 
               
5.75% due 10/20/23 
   
2,000,000
     
1,985,000
 
Mavis Tire 
               
6.25% due 11/02/20†††,1 
   
1,975,000
     
1,953,229
 
Boot Barn Holdings, Inc. 
               
5.50% due 06/29/21†††,1 
   
1,975,000
     
1,950,905
 
Accuride Corp. 
               
8.00% due 11/10/23 
   
2,000,000
     
1,940,000
 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 29


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2016 
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
SENIOR FLOATING RATE INTERESTS††,5 – 38.7% (continued) 
           
Consumer, Cyclical – 7.1% (continued) 
           
BIG JACK Holdings 
           
5.75% due 07/01/22 
   
1,729,783
   
$
1,725,458
 
LA Fitness International LLC 
               
6.00% due 07/01/20 
   
1,277,329
     
1,277,329
 
National Vision, Inc. 
               
6.75% due 03/11/22 
   
1,200,000
     
1,144,500
 
Jacobs Entertainment, Inc. 
               
5.25% due 10/29/18 
   
1,063,037
     
1,063,037
 
MyEye Doctor 
               
7.25% due 08/16/21†††,1 
   
990,396
     
982,632
 
Sky Bet Cyan Blue HoldCo 
               
6.25% due 02/25/22 
 
650,000 GBP
     
817,417
 
Talbots, Inc. 
               
5.50% due 03/19/20 
   
512,371
     
499,561
 
Amaya Holding B.V. 
               
5.00% due 08/01/21 
   
498,737
     
498,194
 
ABRA Auto Body 
               
8.25% due 09/19/22 
   
500,000
     
480,000
 
Ascena Retail Group 
               
5.25% due 08/21/22 
   
403,680
     
392,724
 
Alexander Mann Solutions Ltd. 
               
5.75% due 12/20/19 
   
323,090
     
318,244
 
Ceridian Corp. 
               
4.50% due 09/15/20 
   
300,000
     
294,876
 
Capital Automotive LP 
               
6.00% due 04/30/20 
   
210,000
     
211,224
 
Deb Stores Holding LLC 
               
1.50% due 10/11/16†††,1 
   
728,007
     
1
 
Total Consumer, Cyclical 
           
24,671,357
 
Industrial – 5.9% 
               
Alion Science & Technology Corp. 
               
5.50% due 08/19/21 
   
2,468,750
     
2,416,290
 
CareCore National LLC 
               
5.50% due 03/05/21 
   
2,392,464
     
2,338,633
 
Bioplan / Arcade 
               
5.75% due 09/23/21 
   
1,857,611
     
1,776,340
 
National Technical 
               
7.25% due 06/12/21†††,1 
   
1,641,150
     
1,600,121
 
SRS Distribution, Inc. 
               
9.75% due 02/24/23 
   
1,500,000
     
1,545,000
 
Advanced Integration Tech 
               
6.50% due 07/22/21 
   
1,500,000
     
1,500,000
 
Tronair Parent, Inc. 
               
5.75% due 09/08/23 
   
1,500,000
     
1,485,000
 
 
See notes to financial statements.

30 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2016 
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
SENIOR FLOATING RATE INTERESTS††,5 – 38.7% (continued) 
           
Industrial – 5.9% (continued) 
           
HBC Hardware Holdings 
           
6.75% due 03/30/20††† 
   
1,365,000
   
$
1,337,700
 
SiteOne Landscaping LLC 
               
6.25% due 04/29/22 
   
995,000
     
1,001,219
 
ProAmpac 
               
9.50% due 11/18/24 
   
1,000,000
     
1,000,000
 
Amspec Services, Inc. 
               
6.00% due 07/01/22†††,1 
   
894,737
     
886,414
 
2.09% due 07/01/22†††,1 
   
22,901
     
22,691
 
Ranpak 
               
8.25% due 10/03/22 
   
700,000
     
658,000
 
GYP Holdings III Corp. 
               
4.50% due 04/01/21 
   
626,696
     
626,539
 
Kuehg Corp. 
               
5.25% due 08/12/22 
   
577,583
     
580,835
 
Mast Global 
               
7.75% due 09/12/19†††,1 
   
518,925
     
516,495
 
SI Organization 
               
5.75% due 11/22/19 
   
496,764
     
500,241
 
Hunter Defense Technologies 
               
7.00% due 08/05/19 
   
381,333
     
343,200
 
NaNa Development Corp. 
               
8.00% due 03/15/18 
   
336,176
     
322,729
 
Doncasters Group Ltd. 
               
9.50% due 10/09/20 
   
101,379
     
93,269
 
Carey International, Inc. 
               
9.00% due 05/23/20†††,1 
   
45,978
     
10,989
 
Total Industrial 
           
20,561,705
 
Financial – 2.7% 
               
Hyperion Insurance 
               
5.50% due 04/29/22 
   
1,782,176
     
1,769,363
 
American Stock Transfer & Trust 
               
5.75% due 06/26/20 
   
1,457,789
     
1,443,211
 
Safe-Guard 
               
6.25% due 08/19/21 
   
1,078,667
     
1,035,520
 
Americold Realty Operating Partnership, LP 
               
5.75% due 12/01/22 
   
992,513
     
1,007,400
 
Integro Parent, Inc. 
               
6.75% due 10/31/22 
   
992,785
     
967,965
 
Ryan LLC 
               
6.75% due 08/07/20 
   
937,500
     
928,125
 
Acrisure LLC 
               
5.75% due 11/03/23 
   
845,238
     
844,004
 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 31


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2016 
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
SENIOR FLOATING RATE INTERESTS††,5 – 38.7% (continued) 
           
Financial – 2.7% (continued) 
           
Magic Newco, LLC 
           
12.00% due 06/12/19 
   
750,000
   
$
786,248
 
Assured Partners, Inc. 
               
5.25% due 10/21/22 
   
686,421
     
688,851
 
Total Financial 
           
9,470,687
 
Energy – 1.7% 
               
Invenergy Thermal 
               
6.50% due 10/19/22 
   
1,599,173
     
1,531,208
 
PSS Companies 
               
5.50% due 01/28/20 
   
1,857,824
     
1,319,055
 
Lone Star Energy 
               
5.47% due 02/22/21 
   
1,143,243
     
1,011,433
 
Cactus Wellhead 
               
7.00% due 07/31/20 
   
1,127,760
     
1,000,887
 
Exgen Texas Power LLC 
               
5.75% due 09/18/21 
   
1,120,870
     
850,460
 
Total Energy 
           
5,713,043
 
Basic Materials – 1.6% 
               
Zep, Inc. 
               
5.00% due 06/27/22 
   
1,975,000
     
1,982,406
 
PetroChoice Holdings 
               
6.00% due 08/19/22 
   
1,485,000
     
1,492,425
 
Atkore International, Inc. 
               
7.75% due 10/09/21 
   
1,350,000
     
1,350,000
 
Hoffmaster Group, Inc. 
               
5.50% due 11/10/23 
   
600,000
     
600,000
 
PQ Corp. 
               
5.25% due 11/04/22 
   
200,000
     
201,500
 
Noranda Aluminum Acquisition Corp. 
               
7.00% due 02/28/19 
   
605,414
     
24,217
 
Total Basic Materials 
           
5,650,548
 
Communications – 1.4% 
               
Anaren, Inc. 
               
5.50% due 02/18/21 
   
938,368
     
919,601
 
9.25% due 08/18/21 
   
1,000,000
     
905,000
 
Cengage Learning Acquisitions, Inc. 
               
5.25% due 06/07/23 
   
1,722,642
     
1,652,513
 
Proquest LLC 
               
10.00% due 12/15/22 
   
1,000,000
     
968,750
 
5.75% due 10/24/21 
   
398,983
     
398,652
 
Total Communications 
           
4,844,516
 
 
See notes to financial statements.

32 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2016 
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
   
SENIOR FLOATING RATE INTERESTS††,5 – 38.7% (continued) 
           
Transportation – 1.1% 
           
Travelport Holdings LLC 
           
5.00% due 09/02/21 
   
2,067,981
   
$
2,080,472
 
Capstone Logistics 
               
5.50% due 10/07/21 
   
1,100,000
     
1,081,212
 
Sirva Worldwide, Inc. 
               
7.50% due 11/01/22 
   
525,996
     
514,161
 
Total Transportation 
           
3,675,845
 
Utilities – 0.7% 
               
Panda Power 
               
7.50% due 08/21/20 
   
1,245,987
     
1,216,395
 
Panda Moxie Patriot 
               
6.75% due 12/19/20 
   
900,000
     
879,750
 
Panda Temple II Power 
               
7.25% due 04/03/19 
   
497,744
     
454,191
 
Total Utilities 
           
2,550,336
 
Total Senior Floating Rate Interests 
               
(Cost $135,996,374) 
           
134,318,712
 
COLLATERALIZED MORTGAGE OBLIGATIONS†† – 3.7% 
               
Commercial Mortgage Backed Securities – 2.9% 
               
Cosmopolitan Hotel Trust 
               
2016-CSMO, 5.18% due 11/15/335,6 
   
3,500,000
     
3,519,743
 
GS Mortgage Securities Corporation Trust 
               
2016-ICE2, 9.04% due 02/15/332,5,6 
   
3,000,000
     
3,085,545
 
Capmark Military Housing Trust 
               
2007-AETC, 5.75% due 02/10/522,8 
   
1,920,906
     
1,836,943
 
2007-AET2, 6.06% due 10/10/522,8 
   
486,924
     
493,162
 
Motel 6 Trust 
               
2015-MTL6, 5.28% due 02/05/306 
   
1,200,000
     
1,195,546
 
Total Commercial Mortgage Backed Securities 
           
10,130,939
 
Residential Mortgage Backed Securities – 0.8% 
               
Nomura Resecuritization Trust 
               
2012-1R, 1.05% due 08/27/472,5,6 
   
1,552,658
     
1,523,467
 
TBW Mortgage Backed Pass-Through Certificates 
               
2006-6, 6.04% due 01/25/372,9 
   
1,481,315
     
753,014
 
2006-6, 5.75% due 01/25/372,9 
   
620,622
     
326,144
 
Total Residential Mortgage Backed Securities 
           
2,602,625
 
Total Collateralized Mortgage Obligations 
               
(Cost $12,795,630) 
           
12,733,564
 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 33


     
SCHEDULE OF INVESTMENTS (Unaudited) continued 
 
November 30, 2016 
 
 
 
 
Face
       
 
 
Amount~
   
Value
 
FOREIGN GOVERNMENT BONDS†† – 2.0% 
           
Kenya Government International Bond 
           
6.88% due 06/24/242,6 
   
4,250,000
   
$
4,037,500
 
Dominican Republic International Bond 
               
6.85% due 01/27/452,6 
   
3,050,000
     
2,897,500
 
Total Foreign Government Bonds 
               
(Cost $7,530,217) 
           
6,935,000
 
MUNICIPAL BONDS†† – 0.6% 
               
Illinois – 0.6% 
               
City of Chicago Illinois General Obligation Unlimited 
               
6.26% due 01/01/40 
   
2,350,000
     
2,193,937
 
(Cost $2,034,339) 
               
Total Investments – 142.4% 
               
(Cost $503,253,597) 
         
$
493,885,745
 
 
 
 
Contracts
   
Value
 
CALL OPTIONS WRITTEN†, * – (0.2)% 
           
Call options on: 
           
S&P 500 Index Expiring December 2016 with strike price of $2,190.00 
   
281
   
$
(768,535
)
Total Call Options Written 
               
(Premiums received $701,927) 
         
$
(768,535
)
Other Assets & Liabilities, net – (42.2)% 
           
(146,249,899
)
Total Net Assets – 100.0% 
         
$
346,867,311
 
 
 
       
Unrealized
 
 
 
Contracts
   
Gain
 
EQUITY FUTURES CONTRACTS PURCHASED 
           
December 2016 S&P 500 Index E-Mini Futures Contracts 
           
(Aggregate Value of Contracts $61,901,850) 
   
563
   
$
2,106,966
 
 
 
The face amount is denominated in U.S. Dollars, unless otherwise indicated. 
 
Non-income producing security. 
** 
 
Less than 0.1% 
† 
 
Value determined based on Level 1 inputs, unless otherwise noted — See Note 4. 
†† 
 
Value determined based on Level 2 inputs, unless otherwise noted — See Note 4. 
††† 
 
Value determined based on Level 3 inputs — See Note 4. 
 
Security was fair valued by the Valuation Committee at November 30, 2016. The total market value of 
 
 
fair valued securities amounts to $24,769,863, (cost $32,168,190) or 7.1% of total net assets. 
 
All or a portion of these securities have been physically segregated in connection with borrowings, reverse 
 
 
repurchase agreements and unfunded loan commitments. As of November 30, 2016, the total value of 
 
 
securities segregated was $244,540,462. 
 
See notes to financial statements.

34 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
SCHEDULE OF INVESTMENTS (Unaudited) continued 
November 30, 2016 
 
     
 
Zero coupon rate security. 
 
Rate indicated is the 7-day yield as of November 30, 2016. 
 
Variable rate security. Rate indicated is rate effective at November 30, 2016. 
 
Security is a 144A or Section 4(a)(2) security. These securities have been determined to be liquid under 
 
 
guidelines established by the Board of Trustees. The total market value of 144A or Section 4(a)(2) liquid 
 
 
securities is $224,527,146 (cost $233,325,291), or 64.7% of total net assets. 
 
Security has no stated coupon. However, it is expected to receive residual cash flow payments on defined 
 
 
deal dates. 
 
Security is a 144A or Section 4(a)(2) security. These securities are considered illiquid and restricted under 
 
 
guidelines established by the Board of Trustees. The total market value of 144A or Section 4(a)(2) illiquid 
 
 
and restricted securities is $18,353,438 (cost $25,067,068), or 5.3% of total net assets - see Note 12. 
 
Security is a step up/step down bond. The coupon increases or decreases at regular intervals until the bond 
 
 
reaches full maturity. Rate indicated is rate effective at November 30, 2016. 
10 
 
Perpetual maturity. 
11 
 
Security has a fixed rate coupon which will convert to a floating or variable rate coupon on a future date. 
12 
 
Security is a pay-in-kind bond. 
13 
 
Security is in default. 
14 
 
All or a portion of this security is pledged as futures collateral. 
 
     
B.V. 
 
Limited Liability Company 
CDO 
 
Collateralized Debt Obligation 
CLO 
 
Collateralized Loan Obligation 
EUR 
 
Euro 
FCB 
 
Farmers Credit Bureau 
GBP 
 
Great Britain Pound 
LLC 
 
Limited Liability Company 
LP 
 
Limited Partnership 
N.V. 
 
Publicly Traded Company 
plc 
 
Public Limited Company 
S.A. 
 
Corporation 
SCA 
 
Limited Partnership 

See Sector Classification in Supplemental Information section.

See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 35


   
SCHEDULE OF INVESTMENTS (Unaudited) continued 
November 30, 2016 
 
 
Country Diversification
 
 
 
% of Long-Term
 
Country 
 
Investments
 
United States 
   
90.9
%
Canada 
   
1.9
%
United Kingdom 
   
1.3
%
Netherlands 
   
0.9
%
Luxembourg 
   
0.8
%
Kenya 
   
0.8
%
Marshall Islands 
   
0.8
%
Australia 
   
0.7
%
Dominican Republic 
   
0.6
%
Saint Maarten 
   
0.4
%
France 
   
0.4
%
Niger 
   
0.2
%
Jersey 
   
0.2
%
Ireland 
   
0.1
%
Cayman Islands 
   
0.0
%*
Total Long-Term Investments 
   
100.0
%
*Less than 0.1%. 
       
 
See notes to financial statements.

36 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
SCHEDULE OF INVESTMENTS (Unaudited) continued 
November 30, 2016 
 
The following table represents the Fund’s investments carried on the Statement of Assets and Liabilities by caption and by level within the fair value hierarchy as of November 30, 2016 (see Note 4 in the Notes to Financial Statements):
                         
 
       
Level 2
   
Level 3
       
 
 
Level 1
   
Significant
   
Significant
       
 
 
Quoted
   
Observable
   
Unobservable
       
 
 
Prices
   
Inputs
   
Inputs
   
Total
 
Assets: 
                       
Corporate Bonds 
 
$
   
$
133,594,883
   
$
10,019,257
   
$
143,614,140
 
Asset Backed Securities 
   
     
159,138,799
     
5,561,005
     
164,699,804
 
Collateralized Mortgage Obligations 
   
     
12,733,564
     
     
12,733,564
 
Senior Floating Rate Interests 
   
     
112,407,179
     
21,911,533
     
134,318,712
 
Municipal Bonds 
   
     
2,193,937
     
     
2,193,937
 
Foreign Government Bonds 
   
     
6,935,000
     
     
6,935,000
 
Common Stocks 
   
637,787
     
209,536
     
824,472
     
1,671,795
 
Preferred Stocks 
   
2,920,324
     
     
     
2,920,324
 
Warrants 
   
     
33,784
     
     
33,784
 
U.S. Government Securities 
   
     
24,292,195
     
     
24,292,195
 
Money Market Fund 
   
472,490
     
     
     
472,490
 
Forward Foreign Currency Exchange Contracts* 
   
     
13,745
     
     
13,745
 
Equity Futures Contracts* 
   
2,106,966
     
     
     
2,106,966
 
Total Assets 
 
$
6,137,567
   
$
451,552,622
   
$
38,316,267
   
$
496,006,456
 
   
   
Liabilities: 
                               
Options Written 
   
768,535
     
     
     
768,535
 
Unfunded Commitments 
   
     
717,517
     
     
717,517
 
Forward Foreign Currency Exchange Contracts* 
   
     
61,969
     
     
61,969
 
Total Liabilities 
 
$
768,535
   
$
779,486
   
$
   
$
1,548,021
 
*These amounts are reported as unrealized gain/(loss) as of November 30, 2016.
If not referenced in the table, please refer to the detailed Schedule of Investments for a breakdown of investment type by industry category.
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 37


   
SCHEDULE OF INVESTMENTS (Unaudited) continued 
November 30, 2016 
 
The following is a summary of significant unobservable inputs used in the fair valuation of assets and liabilities categorized within Level 3 of the fair value hierarchy:
         
 
Ending Balance at 
 
 
Input 
Category 
11/30/2016 
Valuation Technique 
Unobservable Inputs 
Range 
Corporate Bonds 
$ 7,531,486 
Option adjusted spread off 
Indicative Quote 
– 
   
the month end broker
   
 
 
quote over the 
 
 
 
 
3 month LIBOR 
 
 
Corporate Bonds 
2,231,750 
Model Price 
Market Comparable Yields 
8.8% – 14.1% 
Corporate Bonds 
256,021 
Model Price 
Liquidation Value 
– 
Asset Backed 
4,061,002 
Option adjusted spread off 
Indicative Quote 
– 
Securities 
 
the month end broker 
 
 
 
 
quote over the 
 
 
 
 
3 month LIBOR 
 
 
Asset Backed 
1,500,000 
Option adjusted spread 
Indicative Quote for 
– 
Securities 
 
 
Comparable Security 
 
Senior Floating 
1,987,700 
Option adjusted spread off 
Indicative Quote 
– 
Rate Interests 
 
the month end broker 
 
 
 
 
quote over the 
 
 
 
 
3 month LIBOR 
 
 
Senior Floating 
685,100 
Enterprise Value 
Valuation Multiple 
5.5x – 7.1x 
Rate Interests 
 
 
 
 
Senior Floating 
7,795,698 
Model Price 
Market Comparable Yields 
4.8% – 5.9% 
Rate Interests 
 
 
 
 
Senior Floating 
11,443,035 
Model Price 
Purchase Price 
– 
Rate Interests 
 
 
 
 
Common Stocks 
387 
Model Price 
Liquidation Value 
– 
Common Stocks 
56,404 
Model Price 
Purchase Price 
– 
Common Stocks 
767,681 
Enterprise Value 
Valuation Multiple 
5.5x – 7.7x 

Significant changes in an indicative quote, liquidation value, market comparable yield or valuation multiple would generally result in significant changes in the fair value of the security.
Any remaining Level 3 securities held by the Fund and excluded from the tables above, were not considered material to the Fund.
Transfers between investment levels may occur as the markets fluctuate and/or the availability of data used in an investment’s valuation changes. Transfers between valuation levels, if any, are in comparison to the valuation levels at the end of the previous fiscal year, and are effective using the fair value as of the end of the current fiscal period.
As of November 30, 2016, the Fund had securities with a total value of $1,520,914 transferred from Level 2 to Level 3 due to lack of multiple vendor prices. As of November 30, 2016, the Fund had securities with a total value of $5,138,400 transferred from Level 3 to Level 2 due to availability of market price information at the period end.

See notes to financial statements.

38 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
SCHEDULE OF INVESTMENTS (Unaudited) continued 
November 30, 2016 
 
Summary of Fair Value Level 3 Activity
Following is a reconciliation of Level 3 assets for which significant unobservable inputs were used to determine fair value for the period ended November 30, 2016:
             
 
 
Senior 
 
 
 
 
 
Asset 
Floating 
Collateralized 
 
 
 
Backed 
Rate 
Corporate 
Mortgage 
Common 
 
 
Securities 
Interests 
Bonds 
 Obligations 
Stocks 
Total 
Assets: 
 
 
 
 
 
 
Beginning 
 
 
 
 
 
 
Balance 
$8,036,285 
$19,029,841 
$8,485,549 
$3,380,625 
$1,079,055 
$40,011,355 
Paydowns 
 
 
 
 
 
 
Received 
(321,057) 
(3,485,092) 
(83,627) 
(18,702) 
– 
(3,908,478) 
Payment-in-kind 
 
 
 
 
 
 
Distributions 
 
 
 
 
 
 
Received 
– 
29,098 
17,507 
– 
– 
46,605 
Realized Gain/ 
 
 
 
 
 
 
Loss 
– 
3,100 
– 
338,151 
– 
341,251 
Change in 
 
 
 
 
 
 
Unrealized 
 
 
 
 
 
 
Gain/Loss 
155,126 
(340,211) 
(55,134) 
(184,146) 
(683,102) 
(1,107,467) 
Accrued 
 
 
 
 
 
 
discounts/ 
 
 
 
 
 
 
(premiums) 
3,108 
43,296 
23,477 
1,112 
– 
70,993 
Purchases 
989,000 
3,432,565 
2,000,000 
– 
60,004 
6,481,569 
Sales 
– 
(373,628) 
– 
(1,680,097) 
– 
(2,053,725) 
Corporate 
 
 
 
 
 
 
actions 
– 
2,051,650 
(368,515) 
– 
368,515 
2,051,650 
Transfers into 
 
 
 
 
 
 
Level 3 
– 
1,520,914 
– 
– 
– 
1,520,914 
Transfers out 
 
 
 
 
 
 
of Level 3 
(3,301,457) 
– 
– 
(1,836,943) 
– 
(5,138,400) 
Ending Balance 
$5,561,005 
$21,911,533 
$10,019,257 
$ – 
$ 824,472 
$38,316,267 
Net change in 
 
 
 
 
 
 
unrealized 
 
 
 
 
 
 
appreciation 
 
 
 
 
 
 
(depreciation) 
 
 
 
 
 
 
for investments 
 
 
 
 
 
 
in securities 
 
 
 
 
 
 
still held at 
 
 
 
 
 
 
November 30, 
 
 
 
 
 
 
2016 
$ 87,932 
$ (348,520) 
$ (55,133) 
$ – 
$ (683,102) 
$ (998,823) 
 
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 39


   
STATEMENT OF ASSETS AND LIABILITIES (Unaudited) 
November 30, 2016 
 
 
ASSETS: 
     
Investments, at value (cost $503,253,597) 
 
$
493,885,745
 
Cash 
   
8,595,041
 
Restricted cash 
   
1,513,469
 
Foreign currency, at value (Cost $37,308) 
   
37,308
 
Unrealized appreciation on forward foreign currency exchange contracts 
   
13,745
 
Receivables: 
       
Investments sold 
   
8,292,922
 
Interest 
   
4,778,820
 
Dividends 
   
6,875
 
Tax reclaims 
   
4,276
 
Other assets 
   
7,094
 
Total assets 
   
517,135,295
 
       
LIABILITIES: 
       
Reverse repurchase agreements 
   
139,786,130
 
Borrowings 
   
14,704,955
 
Written options, at value (premiums received $701,927) 
   
768,535
 
Unfunded loan commitments, at value (Note 10) (Commitment fees received $965,124) 
   
717,517
 
Interest payable on borrowings 
   
321,770
 
Due to broker 
   
240,000
 
Variation margin on futures 
   
135,120
 
Unrealized depreciation on forward foreign currency exchange contracts 
   
61,969
 
Payable for: 
       
Investments purchased 
   
12,662,987
 
Investment advisory fees 
   
398,184
 
Offering costs 
   
309,173
 
Trustees’ fees and expenses* 
   
26,628
 
Accrued expenses and other liabilities 
   
135,016
 
Total liabilities 
   
170,267,984
 
NET ASSETS 
 
$
346,867,311
 
NET ASSETS CONSIST OF: 
       
Common Stock, $0.01 par value per share; unlimited number of shares authorized, 
       
18,507,502 shares issued and outstanding 
 
$
185,075
 
Additional paid-in capital 
   
358,301,149
 
Distributions in excess of net investment income 
   
(13,053,682
)
Accumulated net realized gain on investments 
   
8,576,055
 
Net unrealized depreciation on investments 
   
(7,141,286
)
NET ASSETS 
 
$
346,867,311
 
Net asset value 
 
$
18.74
 
* Relates to Trustees not deemed “interested persons” within the meaning of Section 2(a)(19) of the 1940 Act.

See notes to financial statements.

40 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
STATEMENT OF OPERATIONS 
November 30, 2016 
For the Six Months Ended November 30, 2016 (Unaudited) 
 
 
INVESTMENT INCOME: 
     
Interest 
 
$
18,475,153
 
Dividends 
   
121,974
 
Total investment income 
   
18,597,127
 
EXPENSES: 
       
Investment advisory fees 
   
2,334,552
 
Interest expense 
   
1,196,217
 
Professional fees 
   
103,742
 
Fund accounting fees 
   
58,077
 
Trustees' fees and expenses* 
   
57,279
 
Administration fees 
   
54,212
 
Printing fees 
   
43,860
 
Custodian fees 
   
29,730
 
Registration and filings 
   
13,908
 
Transfer agent fees 
   
10,223
 
Insurance 
   
6,288
 
Miscellaneous 
   
1,332
 
Total expenses 
   
3,909,420
 
Net investment income 
   
14,687,707
 
NET REALIZED AND UNREALIZED GAIN (LOSS): 
       
Net realized gain on: 
       
Investments 
   
4,932,845
 
Foreign currency transactions 
   
974,550
 
Written options 
   
645,568
 
Futures contracts 
   
3,528,442
 
Net realized gain 
   
10,081,405
 
Net change in unrealized appreciation (depreciation) on: 
       
Investments 
   
17,143,727
 
Foreign currency translations 
   
(62,434
)
Written options 
   
584,525
 
Futures contracts 
   
(177,670
)
Net change in unrealized appreciation (depreciation) 
   
17,488,148
 
Net realized and unrealized gain 
   
27,569,553
 
Net increase in net assets resulting from operations 
 
$
42,257,260
 
* Relates to Trustees not deemed “interested persons” within the meaning of Section 2(a)(19) of the 1940 Act.

See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 41


     
STATEMENTS OF CHANGES IN NET ASSETS 
 
November 30, 2016 
 
 
 
 
Period Ended
       
November 30, 2016
   
Year Ended
 
 
 
(Unaudited)
   
May 31, 2016
 
INCREASE (DECREASE) IN NET ASSETS FROM OPERATIONS: 
           
Net investment income 
 
$
14,687,707
   
$
24,660,280
 
Net realized gain on investments 
   
10,081,405
     
6,158,770
 
Net change in unrealized appreciation (depreciation) on investments 
   
17,488,148
     
(29,493,024
)
Net increase in net assets resulting from operations 
   
42,257,260
     
1,326,026
 
DISTRIBUTIONS TO SHAREHOLDERS FROM: 
               
Net investment income 
   
(19,857,283
)
   
(32,113,499
)
Capital gains 
   
     
(6,431,359
)
Total distributions to shareholders 
   
(19,857,283
)
   
(38,544,858
)
SHAREHOLDER TRANSACTIONS: 
               
Net proceeds from shares issued though at-the-market offering 
   
12,886,026
     
3,253,035
 
Reinvestments 
   
1,414,430
     
1,244,253
 
Common share offering costs charged to paid-in capital 
   
(79,306
)
   
(19,815
)
Net increase in net assets resulting from shareholder transactions 
   
14,221,150
     
4,477,473
 
Net increase (decrease) in net assets 
   
36,621,127
     
(32,741,359
)
NET ASSETS: 
               
Beginning of period 
   
310,246,184
     
342,987,543
 
End of period 
 
$
346,867,311
   
$
310,246,184
 
Distributions in excess of net investment income at end of period 
 
$
(13,053,682
)
 
$
(7,884,106
)
 
See notes to financial statements.

42 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
STATEMENT OF CASH FLOWS 
November 30, 2016 
For the Six Months Ended November 30, 2016 (Unaudited) 
 
 
 
Cash Flows from Operating Activities: 
     
Net increase in net assets resulting from operations 
 
$
42,257,260
 
Adjustments to Reconcile Net Increase in Net Assets Resulting from Operations to 
       
Net Cash Used in Operating and Investing Activities: 
       
Net change in unrealized appreciation (depreciation) on investments 
   
(17,143,727
)
Net change in unrealized appreciation (depreciation) on written options 
   
(584,525
)
Net change in unrealized appreciation (depreciation) on foreign currency translations 
   
62,434
 
Net realized gain on investments 
   
(4,932,845
)
Net realized gain on written options 
   
(645,568
)
Net accretion of bond discount and amortization of bond premium 
   
(3,369,178
)
Purchase of long-term investments 
   
(150,794,911
)
Paydowns received on mortgage and asset backed securities 
   
39,236,277
 
Proceeds from written options 
   
4,306,734
 
Cost of closing written options 
   
(3,665,441
)
Proceeds from sales of long-term investments 
   
83,376,295
 
Other payments 
   
226,001
 
Net purchases of short-term investments 
   
(1,262,500
)
Increase in interest receivable 
   
(413,969
)
Decrease in investments sold receivable 
   
4,309,298
 
Decrease in tax reclaims receivable 
   
9,575
 
Increase in other assets 
   
(6,254
)
Decrease in due to broker 
   
(346,000
)
Increase in investments purchased payable 
   
5,511,380
 
Increase in interest payable on borrowings 
   
18,580
 
Commitment fees received on unfunded commitments 
   
(54,317
)
Decrease in variation margin 
   
(40,650
)
Increase in investment advisory fees payable 
   
21,109
 
Increase in trustees' fees and expenses* payable 
   
390
 
Decrease in accrued expenses and other liabilities 
   
(49,509
)
Net Cash Used in Operating and Investing Activities 
 
$
(3,974,061
)
Cash Flows From Financing Activities: 
       
Net proceeds from the issuance of common shares 
   
12,886,026
 
Distributions to common shareholders 
   
(18,442,853
)
Proceeds from reverse repurchase agreements 
   
156,928,033
 
Payments made on reverse repurchase agreements 
   
(147,711,949
)
Proceeds from borrowings 
   
6,250,000
 
Payments made on borrowings 
   
(900,000
)
Offering costs in connection with the issuance of common shares 
   
6,558
 
Net Cash Provided by Financing Activities 
   
9,015,815
 
Net increase in cash 
   
5,041,754
 
Cash at Beginning of Period (including foreign currency and restricted cash) 
   
5,104,064
 
Cash at End of Period (including foreign currency and restricted cash) 
 
$
10,145,818
 
Supplemental Disclosure of Cash Flow Information: Cash paid during the period for interest 
 
$
1,177,637
 
Supplemental Disclosure of Non Cash Financing Activity: Dividend reinvestment 
 
$
1,414,430
 
Supplemental Disclosure of Non Cash Operating Activity: Additional principal received 
       
on payment-in-kind bonds 
 
$
64,858
 
* Relates to Trustees not deemed “interested persons” within the meaning of Section 2(a)(19) of the 1940 Act.
See notes to financial statements.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 43


             
FINANCIAL HIGHLIGHTS 
 
 
November 30, 2016
 
   
Period
                               
   
Ended
                               
 
 
November 30,
   
Year Ended
   
Year Ended
   
Year Ended
   
Year Ended
   
Year Ended
 
 
 
2016
   
May 31,
   
May 31,
   
May 31,
   
May 31,
   
May 31,
 
 
 
(Unaudited)
   
2016
   
2015
   
2014
   
2013
   
2012
 
Per Share Data: 
                                   
Net asset value, beginning of period 
 
$
17.50
   
$
19.61
   
$
20.56
   
$
20.95
   
$
19.00
   
$
20.11
 
Income from investment operations: 
                                               
Net investment income(a) 
   
0.81
     
1.40
     
1.28
     
1.44
     
1.68
     
1.80
 
Net gain (loss) on investments (realized and unrealized) 
   
1.52
     
(1.33
)
   
(0.05
)
   
0.35
     
2.22
     
(1.06
)
Total from investment operations 
   
2.33
     
0.07
     
1.23
     
1.79
     
3.90
     
0.74
 
Less distributions: 
                                               
From and in excess of net investment income 
   
(1.09
)
   
(1.82
)
   
(1.42
)
   
(1.82
)
   
(1.78
)
   
(1.85
)
Capital gains 
   
     
(0.36
)
   
(0.76
)
   
(0.36
)
   
(0.17
)
   
 
Total distributions to shareholders 
   
(1.09
)
   
(2.18
)
   
(2.18
)
   
(2.18
)
   
(1.95
)
   
(1.85
)
Net asset value, end of period 
 
$
18.74
   
$
17.50
   
$
19.61
   
$
20.56
   
$
20.95
   
$
19.00
 
Market value, end of period 
 
$
19.22
   
$
17.61
   
$
21.21
   
$
21.83
   
$
21.91
   
$
21.08
 
Total Return(b) 
                                               
Net asset value 
   
13.58
%
   
0.80
%
   
6.39
%
   
9.20
%
   
21.37
%
   
4.09
%
Market value 
   
15.76
%
   
-6.07
%
   
8.08
%
   
10.71
%
   
14.10
%
   
3.81
%
Ratios/Supplemental Data: 
                                               
Net assets, end of period (in thousands) 
 
$
346,867
   
$
310,246
   
$
342,988
   
$
318,001
   
$
286,471
   
$
207,346
 
Ratio to average net assets applicable to Common Shares: 
                                               
Net investment income, including interest expense 
   
8.79
%(e)
   
7.79
%
   
6.44
%
   
7.07
%
   
8.30
%
   
9.45
%
Total expenses, including interest expense(c)(d) 
   
2.34
%(e)
   
2.38
%
   
2.16
%
   
2.28
%
   
2.47
%
   
2.55
%
Portfolio turnover rate 
   
19
%
   
116
%
   
86
%
   
95
%
   
165
%
   
112
%
 
See notes to financial statements.

44 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


                           
FINANCIAL HIGHLIGHTS continued 
 
 
 
 
 
 
 
 
November 30, 2016 
 
 
   
Period
                               
   
Ended
                               
 
 
November 30,
   
Year Ended
   
Year Ended
   
Year Ended
   
Year Ended
   
Year Ended
 
 
 
2016
   
May 31,
   
May 31,
   
May 31,
   
May 31,
   
May 31,
 
 
 
(Unaudited)
   
2016
   
2015
   
2014
   
2013
   
2012
 
Senior Indebtedness 
                                   
Total Borrowings outstanding (in thousands) 
 
$
154,491
   
$
139,925
   
$
160,247
   
$
136,430
   
$
115,573
   
$
83,842
 
Asset Coverage per $1,000 of indebtedness(f) 
 
$
3,245
   
$
3,217
   
$
3,140
   
$
3,331
   
$
3,479
   
$
3,473
 
 
(a) 
Based on average shares outstanding. 
 
(b) 
Total return is calculated assuming a purchase of a common share at the beginning of the period and a sale on the last day of the period reported either at net asset value 
(“NAV”) or market price per share. Dividends and distributions are assumed to be reinvested at NAV for NAV returns or the prices obtained under the Fund’s Dividend Reinvestment Plan for market value returns. Total return does not reflect brokerage commissions. A return calculated for a period of less than one year is not annualized. 
 
 
(c) 
The ratios of total expenses to average net assets applicable to common shares do not reflect fees and expenses incurred indirectly by the Fund as a result of its investment in 
shares of other investment companies. If these fees were included in the expense ratios, the expense ratios would increase by 0.02%, 0.03%, 0.03%, 0.05% and 0.04% for the 
years ended May 31, 2016, 2015, 2014, 2013 and 2012, respectively. 
 
 
(d) 
Excluding interest expense, the operating expense ratios for the six months ended November 30, 2016 and the years ended May 31 would be: 
 
 
November 30, 
 
 
 
 
 
2016 
2016 
2015 
2014 
2013 
2012 
1.62% 
1.74% 
1.72% 
1.78% 
1.81% 
1.78% 
 
(e) 
Annualized. 
 
 
 
 
 
 
 
 
 
 
 
 
(f) 
Calculated by subtracting the Fund’s total liabilities (not including the borrowings) from the Fund’s total assets and dividing by the total borrowings. 
 
 
 
See notes to financial statements. 

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 45


NOTES TO FINANCIAL STATEMENTS (Unaudited)
November 30, 2016

Note 1 – Organization:
Guggenheim Strategic Opportunities Fund (the “Fund”) was organized as a Delaware statutory trust on November 13, 2006. The Fund is registered as a diversified, closed-end management investment company under the Investment Company Act of 1940, as amended (“1940 Act”).
The Fund’s investment objective is to maximize total return through a combination of current income and capital appreciation.
Note 2 – Accounting Policies:
The Fund operates as an investment company and accordingly follows the investment company accounting and reporting guidance of the Financial Accounting Standards Board (“FASB”) Accounting Standards Codification Topic 946 Financial Services – Investment Companies.
The following significant accounting policies are in conformity with U.S. generally accepted accounting principles (“GAAP”) and are consistently followed by the Fund. This requires management to make estimates and assumptions that affect the reported amount of assets and liabilities and disclosure of contingent assets and liabilities at the date of the financial statements and the reported amounts of revenues and expenses during the reporting period. Actual results could differ from these estimates. All time references are based on Eastern Time.
The following is a summary of significant accounting policies consistently followed by the Fund.
(a) Valuation of Investments
The Board of Trustees of the Fund (the “Board”) has adopted policies and procedures for the valuation of the Fund’s investments (the “Valuation Procedures”). Pursuant to the Valuation Procedures, the Board has delegated to a valuation committee, consisting of representatives from Guggenheim’s investment management, fund administration, legal and compliance departments (the “Valuation Committee”), the day-to-day responsibility for implementing the Valuation Procedures, including, under most circumstances, the responsibility for determining the fair value of the Fund’s securities or other assets.
Valuations of the Fund’s securities are supplied primarily by pricing services appointed pursuant to the processes set forth in the Valuation Procedures. The Valuation Committee convenes monthly, or more frequently as needed and will review the valuation of all assets which have been fair valued for reasonableness. The Fund’s officers, through the Valuation Committee and consistent with the monitoring and review responsibilities set forth in the Valuation Procedures, regularly review procedures used by, and valuations provided by, the pricing services.
If the pricing service cannot or does not provide a valuation for a particular investment or such valuation is deemed unreliable, such investment is fair valued by the Valuation Committee.
Equity securities listed on an exchange (New York Stock Exchange (“NYSE”) or American Stock Exchange) are valued at the last quoted sales price as of the close of business on the NYSE, usually 4:00 p.m. on the valuation date. Equity securities listed on the NASDAQ market system are valued at

46 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


NOTES TO FINANCIAL STATEMENTS (Unaudited) continued
November 30, 2016

the NASDAQ Official Closing Price on the valuation date, which may not necessarily represent the last sale price. If there has been no sale on such exchange or NASDAQ on such day, the security is valued at the closing bid price on such day.
Open-end investment companies (“Mutual Funds”) are valued at their NAV as of the close of business on the valuation date. Exchange Traded Funds (“ETFs”) and closed-end investment companies are valued at the last quoted sale price.
Debt securities with a maturity of greater than 60 days at acquisition are valued at prices that reflect broker/dealer supplied valuations or are obtained from independent pricing services, which may consider the trade activity, treasury spreads, yields or price of bonds of comparable quality, coupon, maturity, and type, as well as prices quoted by dealers who make markets in such securities. Short-term debt securities with a maturity of 60 days or less at acquisition and repurchase agreements are valued at amortized cost, provided such amount approximates market value.
Typically loans are valued using information provided by an independent third party pricing service which uses broker quotes in a non-active market.
Listed options are valued at the Official Settlement Price listed in by the exchange, usually as of 4:00 p.m. Long options are valued using the bid price and short options are valued using the ask price. In the event that a settlement price is not available, fair valuation is enacted. Over-the-counter options are valued using the average bid price (for long options), or average ask price (for short options) obtained from one or more security dealers.
The value of futures contracts is accounted for using the unrealized gain or loss on the contracts that is determined by marking the contracts to their current settlement prices. Financial futures contracts are valued at 4:00 p.m. on the valuation date. In the event that the exchange for a specific futures contract closes earlier than 4:00 p.m., the futures contract is valued at the Official Settlement Price of the exchange. However, the underlying securities from which the futures contract value is derived are monitored until 4:00 p.m. to determine if fair valuation would provide a more accurate valuation.
Generally, trading in foreign securities markets is substantially completed each day at various times prior to the close of the NYSE. The values of foreign securities are determined as of the close of such foreign markets or the close of the NYSE, if earlier. All investments quoted in foreign currency are valued in U.S. dollars on the basis of the foreign currency exchange rates prevailing at the close of U.S. business at 4:00 p.m. Investments in foreign securities may involve risks not present in domestic investments. The Valuation Committee will determine the current value of such foreign securities by taking into consideration certain factors which may include those discussed above, as well as the following factors, among others: the value of the securities traded on other foreign markets, ADR trading, closed-end fund trading, foreign currency exchange activity, and the trading prices of financial products that are tied to foreign securities such as World Equity Benchmark Securities. In addition, under the Valuation Procedures, the Valuation Committee and Guggenheim Funds Investment Advisors, LLC (“GFIA” or the “Adviser”) are authorized to use prices and other information supplied by a third party pricing vendor in valuing foreign securities.

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 47


NOTES TO FINANCIAL STATEMENTS (Unaudited) continued
November 30, 2016

Investments for which market quotations are not readily available are fair valued as determined in good faith by the Adviser, subject to review by the Valuation Committee, pursuant to methods established or ratified by the Board. Valuations in accordance with these methods are intended to reflect each security’s (or asset’s) “fair value.” Each such determination is based on a consideration of all relevant factors, which are likely to vary from one pricing context to another. Examples of such factors may include, but are not limited to: market prices; sale prices; broker quotes; and models which derive prices based on inputs such as prices of securities with comparable maturities and characteristics, or based on inputs such as anticipated cash flows or collateral, spread over Treasuries, and other information analysis.
(b) Investment Transactions and Investment Income
Investment transactions are accounted for on the trade date. Realized gains and losses on investments are determined on the identified cost basis. Paydown gains and losses on mortgage and asset-backed securities are treated as an adjustment to interest income. Dividend income is recorded net of applicable withholding taxes on the ex-dividend date and interest income is recorded on an accrual basis. Discounts or premiums on debt securities purchased are accreted or amortized to interest income over the lives of the respective securities using the effective interest method.
(c) Restricted Cash
A portion of cash on hand relates to collateral received by the Fund for repurchase agreements and futures contracts. This amount is presented on the Statement of Assets and Liabilities as Restricted Cash.
(d) Swaps
A swap is an agreement to exchange the return generated by one instrument for the return generated by another instrument. The Fund enters into swap agreements to manage its exposure to interest rates and/or credit risk or to generate income. Swaps are valued daily at current market value and any unrealized gain or loss is included in the Statement of Assets and Liabilities. Gain or loss is realized on the termination date of the swap and is equal to the difference between the Fund’s basis in the swap and the proceeds of the closing transaction, including any fees. Upon termination of a swap agreement, a payable to or receivable from swap counterparty is established on the Statement of Assets and Liabilities to reflect the net gain/loss, including interest income/expense, on terminated swap positions. The line item is removed upon settlement according to the terms of the swap agreement.
Realized gain (loss) upon termination of swap contracts is recorded on the Statement of Operations. Fluctuations in the value of swap contracts are recorded as a component of net change in unrealized appreciation (depreciation) of swap contracts. Net periodic payments received by the Fund are included as part of realized gain (loss) and, in the case of accruals for periodic payments, are included as part of unrealized appreciation (depreciation) on the Statement of Operations.
As of November 30, 2016, the Fund had no swap contracts outstanding.

48 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
NOTES TO FINANCIAL STATEMENTS (Unaudited) continued 
November 30, 2016 
 
(e) Covered Call Options and Put Options
When an option is written, the premium received is recorded as an asset with an equal liability and is subsequently marked to market to reflect the current market value of the option written. These liabilities are reflected as options written on the Statement of Assets and Liabilities. Premiums received from writing options which expire unexercised are recorded on the expiration date as a realized gain. The difference between the premium received and the amount paid on effecting a closing purchase transaction, including brokerage commissions, is also treated as a realized gain, or if the premium is less than the amount paid for the closing purchase transactions, as a realized loss. If an option is exercised, the premium is added to the proceeds from the sale of the underlying security in determining whether there has been a realized gain or loss.
When a call option is purchased, the Fund obtains the right (but not the obligation) to buy the underlying instrument at the strike price at anytime during the option period. When a put option is purchased, the Fund obtains the right (but not the obligation) to sell the option’s underlying instrument at the strike price at anytime during the option period. When the Fund purchases an option, an amount equal to the premium paid by the Fund is reflected as an asset and subsequently marked-to-market to reflect the current market value of the option purchased. Purchased options are included with Investments on the Statement of Assets and Liabilities. Realized and unrealized gains and losses on purchased options are included with Investments on the Statement of Operations.
(f) Currency Translation
Assets and liabilities denominated in foreign currencies are translated into U.S. dollars at the mean of the bid and ask price of respective exchange rates on the last day of the period. Purchases and sales of investments denominated in foreign currencies are translated at the exchange rate on the bid and ask price of respective exchange rates on the date of the transaction.
The Fund does not isolate that portion of the results of operations resulting from changes in foreign exchange rates on investments from the fluctuations arising from changes in market prices of securities held. Such fluctuations are included with the net realized and unrealized gain or loss from investments.
Foreign exchange realized gain or loss resulting from holding of a foreign currency, expiration of a currency exchange contract, difference in exchange rates between the trade date and settlement date of an investment purchased or sold, and the difference between dividends or interest actually received compared to the amount shown in the Fund’s accounting records on the date of receipt is shown as net realized gains or losses on foreign currency transactions on the Fund’s Statement of Operations.
Foreign exchange unrealized gain or loss on assets and liabilities, other than investments, is shown as unrealized appreciation (depreciation) on foreign currency translation on the Fund’s Statement of Operations.


GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 49


   
NOTES TO FINANCIAL STATEMENTS (Unaudited) continued 
November 30, 2016 

(g) Forward Foreign Currency Exchange Contracts
Forward foreign currency exchange contracts are agreements between two parties to buy and sell currencies at a set price on a future date. Fluctuations in the value of open forward foreign currency exchange contracts are recorded for financial reporting purposes as unrealized appreciation and depreciation by the Fund until the contracts are closed. When the contracts are closed, realized gains and losses are recorded, and included on the Statement of Operations in foreign currency transactions.
(h) Futures Contracts
Upon entering into a futures contract, the Fund deposits and maintains as collateral such initial margin as required by the exchange on which the transaction is affected. Pursuant to the contract, the Fund agrees to receive from or pay to the broker an amount of cash equal to the daily fluctuation in value of the contract.
Such receipts or payments are known as variation margin and are recorded by the Fund as unrealized gains or losses. When the contract is closed, the Fund records a realized gain or loss equal to the difference between the value of the contract at the time it was opened and the value at the time it was closed.
(i) Distributions to Shareholders
The Fund declares and pays monthly distributions to common shareholders. These distributions consist of investment company taxable income, which generally includes qualified dividend income, ordinary income and short-term capital gains. Any net realized long-term capital gains are distributed annually to common shareholders. To the extent distributions exceed taxable income, the excess will be deemed a return of capital.
Distributions to shareholders are recorded on the ex-dividend date. The amount and timing of distributions are determined in accordance with federal income tax regulations, which may differ from GAAP.
(j) Indemnifications
Under the Fund’s organizational documents, its Trustees and Officers are indemnified against certain liabilities arising out of the performance of their duties to the Fund. In addition, throughout the normal course of business, the Fund enters into contracts that contain a variety of representations and warranties which provide general indemnifications. The Fund’s maximum exposure under these arrangements is unknown, as this would involve future claims that may be made against the Fund and/or its affiliates that have not yet occurred. However, based on experience, the Fund expects the risk of loss to be remote.

50 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
NOTES TO FINANCIAL STATEMENTS (Unaudited) continued 
November 30, 2016 
 

Note 3 – Investment Advisory Agreement, Sub-Advisory Agreement and Other Agreements: 
 
 
Pursuant to an Investment Advisory Agreement between the Fund and the Adviser, the Adviser furnishes offices, necessary facilities and equipment, provides administrative services, oversees the activities of Guggenheim Partners Investment Management, LLC (“GPIM” or “Sub-Adviser”), provides personnel including certain officers required for the Fund’s administrative management and compensates the officers and trustees of the Fund who are affiliates of the Adviser. As compensation for these services, the Fund pays the Adviser a fee, payable monthly, in an amount equal to 1.00% of the Fund’s average daily managed assets (net assets applicable to common shareholders plus any assets attributable to financial leverage).
Pursuant to a Sub-Advisory Agreement among the Fund, the Adviser and GPIM, GPIM, under the supervision of the Fund’s Board of Trustees and the Adviser, provides a continuous investment program for the Fund’s portfolio; provides investment research; makes and executes recommendations for the purchase and sale of securities; and provides certain facilities and personnel, including certain officers required for its administrative management and pays the compensation of all officers and trustees of the Fund who are GPIM’s affiliates. As compensation for its services, the Adviser pays GPIM a fee, payable monthly, in an annual amount equal to 0.50% of the Fund’s average daily managed assets.
For purposes of calculating the fees payable under the foregoing agreements, average daily managed assets means the average daily value of the Fund’s total assets minus the sum of its accrued liabilities. Total assets means all of the Fund’s assets and is not limited to its investment securities. Accrued liabilities means all of the Fund’s liabilities other than borrowings for investment purposes.
Certain officers and trustees of the Fund may also be officers, directors and/or employees of the Adviser or GPIM. The Fund does not compensate its officers or trustees who are officers, directors and/or employees of the aforementioned firms.
On October 4, 2016, Rydex Fund Services, LLC (“RFS”) was purchased by MUFG Investor Services and as of that date RFS ceased to be an affiliate of the Adviser. In connection with its acquisition, RFS changed its name to MUFG Investor Services (US), LLC (“MUIS”). This change has no impact on the financial statements of the Fund.
MUIS acts as the Fund’s administrator and accounting agent. As administrator and accounting agent, MUIS is responsible for maintaining the books and records of the Fund’s securities and cash. The Bank of New York (“BNY”) acts as the Fund’s custodian. As custodian, BNY is responsible for the custody of the Fund’s assets. For providing the aforementioned services, MUIS and BNY are entitled to receive a monthly fee equal to an annual percentage of the Fund’s average daily managed assets subject to certain minimum monthly fees and out of pocket expenses.
 

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 51


   
NOTES TO FINANCIAL STATEMENTS (Unaudited) continued
November 30, 2016
 
Note 4 – Fair Value Measurement:
In accordance with GAAP, fair value is defined as the price that the Fund would receive to sell an investment or pay to transfer a liability in an orderly transaction with an independent buyer in the principal market, or in the absence of a principal market, the most advantageous market for the investment or liability. GAAP establishes a three-tier fair value hierarchy based on the types of inputs used to value assets and liabilities and requires corresponding disclosure. The hierarchy and the corresponding inputs are summarized below:
Level 1 — quoted prices in active markets for identical assets or liabilities.
Level 2 — significant other observable inputs (for example quoted prices for securities that are similar based on characteristics such as interest rates, prepayment speeds, credit risk, etc.).
Level 3 — significant unobservable inputs based on the best information available under the circumstances, to the extent observable inputs are not available, which may include assumptions.
The types of inputs available depend on a variety of factors, such as the type of security and the characteristics of the markets in which it trades, if any. Fair valuation determinations that rely on fewer or no observable inputs require greater judgment. Accordingly, fair value determinations for Level 3 securities require the greatest amount of judgment.
Independent pricing services are used to value a majority of the Fund’s investments. When values are not available from a pricing service, they will be determined under the valuation policies that have been reviewed and approved by the Board. In any event, values are determined using a variety of sources and techniques, including: market prices; broker quotes; and models which derive prices based on inputs such as prices of securities with comparable maturities and characteristics or based on inputs such as anticipated cash flows or collateral, spread over Treasuries, and other information and analysis. A significant portion of the Funds’ assets and liabilities are categorized as Level 2 or Level 3, as indicated in this report.
Indicative quotes from broker-dealers, adjusted for fluctuations in criteria such as credit spreads and interest rates, may be also used to value the Fund’s assets and liabilities, i.e. prices provided by a broker-dealer or other market participant who has not committed to trade at that price. Although indicative quotes are typically received from established market participants, the Fund may not have the transparency to view the underlying inputs which support the market quotations.
Certain fixed income securities are valued by obtaining a monthly indicative quote from a broker-dealer, adjusted for fluctuations in criteria such as credit spreads and interest rates. The Fund’s fair valuation guidelines categorize these securities as Level 3.
The inputs or methodologies used for valuing securities are not necessarily an indication of the risk associated with investing in those securities. The suitability of the techniques and sources employed to determine fair valuation are regularly monitored and subject to change.
 

52 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
NOTES TO FINANCIAL STATEMENTS (Unaudited) continued
November 30, 2016
 
Note 5 – Federal Income Taxes:
The Fund intends to comply with the requirements of Subchapter M of the Internal Revenue Code of 1986, as amended, (the “Internal Revenue Code”), applicable to regulated investment companies.
The Fund may be subject to an excise tax of 4% of the amount by which 98% of the Fund’s annual taxable income and 98.2% of net realized gains exceed the distributions from such taxable income and realized gains for the calendar year.
As of November 30, 2016, the cost of investments and accumulated unrealized appreciation/ (depreciation) of investments for federal income tax purposes, were as follows:
                 
Net Tax
 
     
Gross Tax
   
Gross
   
Unrealized
 
Cost of Investments
   
Unrealized
   
Tax Unrealized
   
Depreciation
 
for Tax Purposes
   
Appreciation
   
Depreciation
   
on Investments
 
$
511,637,705
   
$
22,789,162
   
$
(40,541,122
)
 
$
(17,751,960
)
 
The differences between book basis and tax basis unrealized appreciation (depreciation) is primarily attributable to the tax deferral of losses on wash sales, equity to debt income accruals, collateralized loan obligations, and the marking to market of forward foreign currency contracts, futures contracts and options contracts.
As of May 31, 2016 (the most recent fiscal year end for federal income tax purposes), the tax components of accumulated earnings/losses (excluding paid-in capital) on a tax basis were as follows:
     
Undistributed
       
     
Long-Term Capital
       
Undistributed
   
Gains/(Accumulated
   
Net Unrealized
 
Ordinary Income
   
Capital and Other Losses)
   
Depreciation
 
$
520,395
   
$
129,983
   
$
(34,669,268
)
 
For the year ended May 31, 2016 (the most recent fiscal year end for federal income tax purposes), the tax character of distributions paid to shareholders as reflected in the Statements of Changes in Net Assets was as follows:
Distributions paid from 
     
Ordinary income 
 
$
32,113,499
 
Long –term capital gain 
   
6,431,359
 
 
 
$
38,544,858
 

For all open tax years and all major jurisdictions, management of the Fund has concluded that there are no significant uncertain tax positions that would require recognition in the financial statements. Uncertain tax positions are tax positions taken or expected to be taken in the course of preparing the Fund’s tax returns that would not meet a more-likely-than not threshold of being sustained by the applicable tax authority and would be recorded as a tax expense in the current year. Open tax years
 

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 53


   
NOTES TO FINANCIAL STATEMENTS (Unaudited) continued Note 5 – Federal Income Taxes:
November 30, 2016

are those that are open for examination by taxing authorities (i.e. generally the last four tax year ends and the interim tax period since then).
Note 6 – Investments in Securities:
During the six months ended November 30, 2016, the cost of purchases and proceeds from sales of investments, excluding written options, futures contracts and short-term investments, were $150,794,911 and $83,376,295, respectively.
The Fund is permitted to purchase or sell securities from or to certain affiliated funds under specified conditions outlined in procedures adopted by the Board. The procedures have been designed to ensure that any purchase or sale of securities by the Fund from or to another fund or portfolio that is or could be considered an affiliate by virtue of having a common investment adviser (or affiliated investment advisers), common trustees and/or common officers complies with Rule 17a-7 of the 1940 Act. Further, as defined under these procedures, each transaction is effected at the current market price to save costs, where permissible. For the six months ended November 30, 2016, the Fund engaged in purchases and sales of securities, pursuant to Rule 17a-7 of the 1940 Act, as follows:
Purchases 
Sales 
Realized Gain 
$2,056,813 
$1,052,500 
$52,500 
 
Note 7 – Derivatives:
Derivatives are instruments whose values depend on, or are derived from, in whole or in part, the value of one or more other assets, such as securities, currencies, commodities or indices. Derivative instruments may be used to increase investment flexibility (including to maintain cash reserves while maintaining exposure to certain other assets), for risk management (hedging) purposes, to facilitate trading, to reduce transaction costs and to pursue higher investment returns. Derivative instruments may also be used to mitigate certain investment risks, such as foreign currency exchange rate risk, interest rate risk and credit risk. GAAP requires disclosures to enable investors to better understand how and why a Fund uses derivative instruments, how these derivative instruments are accounted for and their effects on the Fund’s financial position and results of operations.
The Fund may utilize derivatives for the following purposes:
Hedge – an investment made in order to seek to reduce the risk of adverse price movements in a security, by taking an offsetting position to protect against broad market moves.
 

54 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
NOTES TO FINANCIAL STATEMENTS (Unaudited) continued
November 30, 2016
 
(a) Covered Call Options and Put Options

The Fund pursues its investment objective by employing an option strategy of writing (selling) covered call options and, from time to time, buys or sells put options on equity securities and indices. The Fund seeks to generate current gains from option premiums as a means to enhance distributions payable to the Fund’s common shareholders.
An option on a security is a contract that gives the holder of the option, in return for a premium, the right to buy from (in the case of a call) or sell to (in the case of a put) the writer of the option the security underlying the option at a specified exercise or “strike” price. The writer of an option on a security has the obligation upon exercise of the option to deliver the underlying security upon payment of the exercise price (in the case of a call) or to pay the exercise price upon delivery of the underlying security (in the case of a put).
There are several risks associated with transactions in options on securities. As the writer of a covered call option, the Fund forgoes, during the option’s life, the opportunity to profit from increases in the market value of the security covering the call option above the sum of the premium and the strike price of the call, but has retained the risk of loss should the price of the underlying security decline. A writer of a put option is exposed to the risk of loss if the fair value of the underlying security declines, but profits only to the extent of the premium received if the underlying security increases in value. The writer of an option has no control over the time when it may be required to fulfill its obligation as writer of the option. Once an option writer has received an exercise notice, it cannot effect a closing purchase transaction in order to terminate its obligation under the option and must deliver the underlying security at the exercise price.
To the extent that the Fund purchases options, the Fund will be subject to the following additional risks. If a put or call option purchased by the Fund is not sold when it has remaining value, and if the market price of the underlying security remains equal to or greater than the exercise price (in the case of a put), or remains less than or equal to the exercise price (in the case of a call), the Fund will lose its entire investment in the option. Also, where a put or call option on a particular security is purchased to hedge against price movements in a related security, the price of the put or call option may move more or less than the price of the related security. If restrictions on exercise were imposed, the Fund might be unable to exercise an option it had purchased. If the Fund were unable to close out an option that it had purchased on a security, it would have to exercise the option in order to realize any profit or the option may expire worthless. The maximum exposure the Fund has at risk when purchasing an option is the premium paid.
The Fund entered into written option contracts during the six months ended November 30, 2016.
 

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 55


     
NOTES TO FINANCIAL STATEMENTS (Unaudited) continued 
November 30, 2016 
 
 
Details of the transactions were as follows: 
 
 
 
 
 
Number of
   
Premiums
 
 
 
Contracts
   
Received
 
Options outstanding, beginning of the period 
   
279
   
$
706,202
 
Options written during the period 
   
1,660
     
4,306,734
 
Options expired during the period 
   
     
 
Options closed during the period 
   
(1,658
)
   
(4,311,009
)
Options assigned during the period 
   
     
 
Options outstanding, end of period 
   
281
   
$
701,927
 

(b) Swaps
Swap agreements are contracts between parties in which one party agrees to make periodic payments to the other party (the “Counterparty”) based on the change in market value or level of a specified rate, index or asset. In return, the Counterparty agrees to make periodic payments to the first party based on the return of a different specified rate, index or asset. Swap agreements will usually be done on a net basis, the Fund receiving or paying only the net amount of the two payments. The net amount of the excess, if any, of each Fund’s obligations over its entitlements with respect to each swap is accrued on a daily basis and an amount of cash or liquid securities having an aggregate value at least equal to the accrued excess is maintained in an account at the Fund’s custodian bank. During the period that the swap agreement is open, the Fund may be subject to risk from the potential inability of the counterparty to meet the terms of the agreement. The swaps involve elements of both market and credit risk in excess of the amounts reflected on the Statement of Assets and Liabilities.
Credit default swap transactions involve the Fund’s agreement to exchange the credit risk of an issuer. A buyer of a credit default swap is said to buy protection by paying periodic fees in return for a contingent payment from the seller if the issuer has a credit event such as bankruptcy, a failure to pay outstanding obligations or deteriorating credit while the swap is outstanding. A seller of a credit default swap is said to sell protection and thus collects the periodic fees and profits if the credit of the issuer remains stable or improves while the swap is outstanding but the seller in a credit default swap contract would be required to pay an agreed upon amount, which approximates the notional amount of the swap, to the buyer in the event of an adverse credit event of the issuer.
The Fund may utilize index swap transactions to manage its exposure to various securities markets, changes in interest rates, or currency values. Index swap transactions allow the Fund to receive the appreciation/depreciation of the specified index over a specified time period in exchange for an agreed upon fee paid to the counterparty.
The Fund did not have any swap agreements outstanding as of November 30, 2016.
 

56 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
NOTES TO FINANCIAL STATEMENTS (Unaudited) continued 
November 30, 2016 
 
(c) Forward Foreign Currency Exchange Contracts
The Fund enters into forward foreign currency exchange contracts in order to hedge its exposure to changes in foreign currency exchange rates on its foreign portfolio holdings, to hedge certain firm purchases and sales commitments denominated in foreign currencies and for investment purposes.
A forward foreign currency exchange contract is a commitment to purchase or sell a foreign currency on a future date at a negotiated forward rate. Forward foreign currency exchange contracts involve elements of both market and credit risk in excess of the amounts reflected on the Statement of Assets and Liabilities. Risk may arise from the potential inability of a counterparty to meet the terms of a contract and from unanticipated movements in the value of a foreign currency relative to the U.S. dollar. The face or contract amount, in U.S. dollars, reflects the total exposure the Fund has in that particular currency contract.
As of November 30, 2016, the following forward foreign currency exchange contracts were outstanding:
 
     
 
 
             
Net Unrealized
 
 
     
   
Settlement 
 
Settlement
   
Value as of
   
Appreciation
 
Contracts to Sell
 
Counterparty 
Date 
 
Value
   
11/30/16
   
(Depreciation)
 
EUR 
   
323,000
 
 
 
                 
for USD 
   
356,288
 
Bank of America Merrill Lynch 
12/12/2016 
 
$
356,288
   
$
342,543
   
$
13,745
 
GBP 
   
5,117,000
 
 
 
                       
for USD 
   
6,341,385
 
Bank of America Merrill Lynch 
12/12/2016 
   
6,341,385
     
6,403,354
     
(61,969
)
 
       
 
 
                 
$
(48,224
)

(d) Futures Contracts

A futures contract is an agreement to purchase (long) or sell (short) an agreed amount of securities or other instruments at a set price for delivery at a future date. There are significant risks associated with a Fund’s use of futures contracts, including (i) there may be an imperfect or no correlation between the changes in market value of the underlying asset and the prices of futures contracts; (ii) there may not be a liquid secondary market for a futures contract; (iii) trading restrictions or limitations may be imposed by an exchange; and (iv) government regulations may restrict trading in futures contracts. When investing in futures, there is minimal counterparty credit risk to the Fund because futures are exchange-traded and the exchange’s clearinghouse, as counterparty to all exchange-traded futures, guarantees against default. Cash deposits are shown as segregated cash with broker on the Statement of Assets and Liabilities; securities held as collateral are noted on the Schedule of Investments.
(e) Summary of Derivatives Information
The Fund is required by GAAP to disclose: a) how and why a fund uses derivative instruments, b) how derivative instruments and related hedge fund items are accounted for, and c) how derivative instruments and related hedge items affect a fund’s financial position, results of operations and cash flows.
 

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 57


   
NOTES TO FINANCIAL STATEMENTS (Unaudited) continued 
November 30, 2016 
 
The following table presents the types of derivatives in the Fund by location as presented on the Statement of Assets and Liabilities as of November 30, 2016.
Statement of Asset and Liabilities
Presentation of Fair Values of Derivative Instruments (value in $000s):
 
Asset Derivatives 
 
Liability Derivatives 
 
Primary Risk Exposure 
Statement of Assets 
and Liabilities Location 
Fair Value 
 
Statement of Assets 
and Liabilities Location 
Fair Value 
Equity risk 
 
$ – 
 
Options Written 
$769 
Equity risk 
Unrealized appreciation on 
2,107 
 
Unrealized depreciation on 
– 
 
futures contracts* 
 
 
futures contracts* 
 
Foreign exchange risk 
Unrealized appreciation on 
 
 
Unrealized depreciation on 
 
 
forward foreign currency 
 
 
forward foreign currency 
 
 
exchange contracts 
14 
 
exchange contracts 
62 
Total 
 
$2,121 
 
 
$831 
 
*  Includes cumulative appreciation (depreciation) of futures contracts as reported on the Schedule of Investments. Only current day’s variation margin is reported within the Statement of Assets and Liabilities. 
 
The following table presents the effect of derivative instruments on the Statement of Operations for the six months ended November 30, 2016.
         
Effect of Derivative Instruments on the Statement of Operations
 
Amount of Realized Gain (Loss) on Derivatives (value in $000s):
 
Primary Risk 
Written 
Foreign Currency 
Futures 
 
Exposure 
Options 
Transactions 
Contracts 
Total 
Equity risk 
$646 
$ – 
$ 3,528 
$ 4,174 
Foreign exchange risk 
– 
975 
– 
975 
Total 
$646 
$ 975 
$ 3,528 
$ 5,149 
 
Change in Unrealized Appreciation (Depreciation) on Derivatives (value in $000s):
 
Primary 
Written 
Foreign Currency 
Futures 
 
Risk Exposure 
Options 
Translations 
Contracts 
Total 
Equity risk 
$585 
$ –    
$ (178) 
$ 407 
Foreign exchange risk 
– 
(71)* 
–   
(71)
Total 
$585 
$ (71)  
$ (178) 
$ 336 
*  The Statement of Operations includes change in unrealized appreciation (depreciation) on foreign currency and payables or receivables in foreign currency.
 

58 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
NOTES TO FINANCIAL STATEMENTS (Unaudited) continued 
November 30, 2016 
 
Derivative Volume

Forward Foreign Currency Exchange Contracts:
The Fund had the following activity in forward foreign currency exchange contracts during the six months ended November 30, 2016:
Quarterly Average Settlement Value Purchased 
 
$
 
Quarterly Average Settlement Value Sold 
   
7,324,746
 
 
Futures Contracts:
The Fund had the following activity in futures contracts during the six months ended November 30, 2016:
Quarterly Average Notional Value 
 
$
61,750,725
 
 
Note 8 – Offsetting:
In the normal course of business, the Fund enters into transactions subject to enforceable master netting arrangements or other similar arrangements. Generally, the right to offset in those agreements allows the Fund to counteract the exposure to a specific counterparty with collateral received or delivered to that counterparty based on the terms of the arrangements. These arrangements provide for the right to liquidate upon the occurrence of an event of default, credit event upon merger or additional termination event.
In order to better define their contractual rights and to secure rights that will help the Fund mitigate their counterparty risk, the Fund may enter into an International Swaps and Derivatives Association, Inc. Master Agreement (“ISDA Master Agreement”) or similar agreement with their derivative contract counterparties. An ISDA Master Agreement is a bilateral agreement between a Fund and a counterparty that governs OTC derivatives, including foreign exchange contracts, and typically contains, among other things, collateral posting terms and netting provisions in the event of a default and/or termination event. The provisions of the ISDA Master Agreement typically permit a single net payment in the event of a default (close-out netting) or similar event, including the bankruptcy or insolvency of the counterparty.
For derivatives traded under an ISDA Master Agreement, the collateral requirements are typically calculated by netting the mark to market amount for each transaction under such agreement and comparing that amount to the value of any collateral currently pledged by the Fund and the counterparty. For financial reporting purposes, cash collateral that has been pledged to cover obligations of the Fund and cash collateral received from the counterparty, if any, is reported separately on the Statement of Assets and Liabilities as segregated cash with broker/ receivable for variation margin, or payable for swap settlement/variation margin. Generally, the amount of collateral due from or to a counterparty must exceed a minimum transfer amount threshold (e.g., $300,000) before a transfer is required to be made. To the extent amounts due to the Fund from its counterparties are not fully collateralized, contractually or otherwise, the Fund bears the risk of loss from counterparty nonperformance. The Fund attempts to mitigate counterparty risk by only

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 59

 
   
NOTES TO FINANCIAL STATEMENTS (Unaudited) continued 
November 30, 2016 
 
entering into agreements with counterparties that it believes to be of good standing and by monitoring the financial stability of those counterparties.
For financial reporting purposes, the Fund does not offset derivative assets and derivative liabilities that are subject to netting arrangements in the Statement of Assets and Liabilities.
The following tables present derivative financial instruments and secured financing transactions that are subject to enforceable netting arrangements and offset in the Statements of Assets and Liabilities in conformity with GAAP.
             
 
 
 
 
Net Amounts 
 
 
 
 
 
Gross Amounts 
of Assets 
Gross Amounts Not 
 
 
 
Gross 
Offset in the 
Presented in the 
Offset in the Statement 
 
 
 
Amounts of 
Statement of 
Statement of 
of Assets and Liabilities 
 
 
 
Recognized 
Assets and 
Assets and 
Financial 
 
Description 
 
Assets 
Liabilities 
Liabilities 
Instruments 
Net Amount 
Forward Foreign 
 
 
 
 
 
Currency 
 
 
 
 
 
 
Exchange 
 
 
 
 
 
 
Contracts 
$ 13,745 
$ – 
$ 13,745 
$ 13,745 
$ – 
 
 
 
 
 
Net Amounts 
 
 
 
 
 
Gross Amounts 
of Liabilities 
Gross Amounts Not 
 
 
 
Gross 
Offset in the 
Presented in the 
Offset in the Statement 
 
 
 
Amounts of 
Statement of 
Statement of 
of Assets and Liabilities 
 
 
 
Recognized 
Assets and 
Assets and 
Financial 
 
Description 
 
Liabilities 
Liabilities 
Liabilities 
Instruments 
Net Amount 
Reverse Repurchase 
 
 
 
 
 
Agreements 
$ 139,786,130 
$ – 
$ 139,786,130 
$ 139,786,130 
$         – 
Forward Foreign 
 
 
 
 
 
Currency Exchange 
 
 
 
 
 
Contracts 
 
61,969 
– 
61,969 
13,745 
48,224 
 
Note 9 – Leverage:
Reverse Repurchase Agreements
The Fund may enter into reverse repurchase agreements as part of its financial leverage strategy. Under a reverse repurchase agreement, the Fund temporarily transfers possession of a portfolio instrument to another party, such as a bank or broker-dealer, in return for cash. At the same time, the Fund agrees to repurchase the instrument at an agreed upon time and price, which reflects an interest payment. Such agreements have the economic effect of borrowings. The Fund may enter into such agreements when it is able to invest the cash acquired at a rate higher than the cost of the agreement, which would increase earned income. When the Fund enters into a reverse repurchase agreement, any fluctuations in the market value of either the instruments transferred to another party or the instruments in which the proceeds may be invested would affect the market value of the Fund’s assets. As a result, such transactions may increase fluctuations in the market value of the Fund’s assets. For the six months ended November 30, 2016, the average daily balance of reverse
 

60 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
NOTES TO FINANCIAL STATEMENTS (Unaudited) continued 
November 30, 2016 
 
repurchase agreements outstanding amounted to $121,707,652. The weighted average interest rate was 1.81%. As of November 30, 2016, there was $139,786,130 in reverse repurchase agreements outstanding.
As of November 30, 2016, the Fund had outstanding reverse repurchase agreements with various counterparties. Details of the reverse repurchase agreements by counterparty are as follows:
Counterparty 
Interest Rates 
Maturity Dates 
Face Value 
Bank of America 
1.57% - 1.96% 
12/05/16 – 01/12/17 
$    8,753,198 
Barclays Capital, Inc. 
0.00% - 2.28% 
12/01/16 – 01/05/17 
17,785,244 
Barclays Capital, Inc. 
0.00% - 1.00%* 
Open maturity 
1,795,403 
BNP Paribas 
1.48% - 1.87% 
12/02/16 – 03/01/17 
27,118,687 
Citigroup Global Markets, Inc. 
0.00% 
Open maturity 
268,000 
Credit Suisse First Boston 
1.50% - 1.80% 
12/05/16 – 01/06/17 
9,416,487 
Credit Suisse First Boston 
0.75% - 1.55%* 
Open maturity 
2,440,156 
JPM Securities 
1.74% - 1.92% 
12/08/16 – 12/09/16 
5,195,000 
Morgan Stanley, Inc. 
1.63% - 2.34% 
12/07/16 – 02/27/17 
14,516,650 
Nomura 
2.18% - 2.69% 
09/05/17 – 11/07/17 
15,192,194 
Nomura 
1.40%* 
Open maturity 
3,931,313 
RBC Capital 
1.33% - 1.81% 
12/05/2016 – 03/01/17 
22,882,548 
RBC Capital 
1.30%* 
Open maturity 
397,250 
Royal Bank of Canada 
2.17% - 2.38% 
01/12/17 – 02/07/17 
1,828,000 
Societe Generale 
1.93% - 2.43% 
12/02/16 – 02/24/17 
7,347,000 
Wells Fargo Bank, Ltd. 
1.79% 
12/07/16 
919,000 
 
 
 
$139,786,130 
* Variable rate security. Rate indicated is rate effective as of November 30, 2016.
The following is a summary of the remaining contractual maturities of the reverse repurchase agreements outstanding as of November 30, 2016, aggregated by asset class of the related collateral pledged by the Fund:
                               
 
 
Overnight and
   
Up to
     
31 - 90
   
Greater than
       
 
 
Continuous
   
30 days
   
days
   
90 days
   
Total
 
Asset Backed Securities 
 
$
   
$
28,611,350
   
$
7,393,000
   
$
4,574,750
   
$
40,579,100
 
Collateralized Mortgage 
                                       
Obligations 
   
     
1,950,000
     
     
     
1,950,000
 
Corporate Bonds 
   
7,105,810
     
19,784,420
     
44,819,953
     
20,091,866
     
91,802,049
 
Foreign Government Bonds 
   
1,726,312
     
1,326,750
     
2,401,919
     
     
5,454,981
 
Total Borrowings 
 
$
8,832,122
   
$
51,672,520
   
$
54,614,872
   
$
24,666,616
   
$
139,786,130
 
Gross amount of recognized 
                                       
liabilities for reverse 
                                       
repurchase agreements 
 
$
8,832,122
   
$
51,672,520
   
$
54,614,872
   
$
24,666,616
   
$
139,786,130
 
 
 

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 61


   
NOTES TO FINANCIAL STATEMENTS (Unaudited) continued 
November 30, 2016 
 
Borrowings
The Fund has entered into a $80,000,000 credit facility agreement with an approved lender whereby the lender has agreed to provide secured financing to the Fund and the Fund will provide pledged collateral to the lender. Interest on the amount borrowed is based on the 3-month LIBOR plus 0.85%. As of November 30, 2016, there was $14,704,955 outstanding in connection with the Fund’s credit facility. The average daily amount of borrowings on the credit facility during the six months ended November 30, 2016, was $10,793,206 with a related average interest rate of 1.69%. The maximum amount outstanding during the six months ended November 30, 2016 was $14,704,955. As of November 30, 2016, the total value of securities segregated and pledged as collateral in connection with borrowings was $28,141,181.
The credit facility agreement governing the loan facility includes usual and customary covenants. These covenants impose on the Fund asset coverage requirements, collateral requirements, investment strategy requirements, and certain financial obligations. These covenants place limits or restrictions on the Fund’s ability to (i) enter into additional indebtedness with a party other than the counterparty, (ii) change its fundamental investment policy, or (iii) pledge to any other party, other than to the counterparty, securities owned or held by the Fund over which the counterparty has a lien. In addition, the Fund is required to deliver financial information to the counterparty within established deadlines, maintain an asset coverage ratio (as defined in Section 18(g) of the 1940 Act) greater than 300%, comply with the rules of the stock exchange on which its shares are listed, and maintain its classification as a “closed-end management investment company” as defined in the 1940 Act.
There is no guarantee that the Fund’s leverage strategy will be successful. The Fund’s use of leverage may cause the Fund’s NAV and market price of common shares to be more volatile and can magnify the effect of any losses.
Note 10 – Loan Commitments
Pursuant to the terms of certain Term Loan agreements, the Fund held unfunded loan commitments as of November 30, 2016. The Fund is obligated to fund these loan commitments at the borrower’s discretion. The Fund reserves against such contingent obligations by designating cash, liquid securities, and liquid term loans as a reserve. As of November 30, 2016, the total amount segregated in connection with reverse repurchase agreements and unfunded commitments was $216,399,281.
 

62 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
NOTES TO FINANCIAL STATEMENTS (Unaudited) continued 
November 30, 2016 
 
As of November 30, 2016, the Fund had the following unfunded loan commitments which could be extended at the option of the borrower:
Borrower 
Maturity Date 
 
Face Amount
   
Value
 
Acosta, Inc. 
09/26/2019 
 
$
1,100,000
   
$
82,562
 
Acrisure LLC 
11/03/2023 
   
154,762
     
226
 
American Seafoods Group LLC 
08/19/2021 
   
500,000
     
58,606
 
Amspec Services, Inc. 
07/01/2022 
   
82,362
     
755
 
Aspect Software, Inc. 
05/25/2018 
   
20,833
     
 
Deltek, Inc. 
06/25/2020 
   
1,500,000
     
133,108
 
Eyemart Express 
12/18/2019 
   
500,000
     
36,962
 
Globallogic Holdings, Inc. 
11/30/2018 
   
300,000
     
22,949
 
Gold Merger, Co. 
07/27/2021 
   
1,000,000
     
 
Grinding Media, Inc. 
03/03/2017 
   
350,000
     
 
Hostess Brands 
08/03/2020 
   
500,000
     
 
Insight Fourth Hospitality 
07/15/2020 
   
500,000
     
56,603
 
IntraWest Holdings 
12/10/2018 
   
200,000
     
3,233
 
MRI Software LLC 
10/03/2021 
   
81,818
     
 
National Technical 
06/12/2021 
   
305,882
     
2,462
 
Packaging Coordinators Midco, Inc. 
07/01/2021 
   
1,384,615
     
158,653
 
Pelican Products, Inc. 
04/11/2019 
   
300,000
     
21,163
 
PowerSchool, Inc. 
07/29/2021 
   
525,000
     
51,002
 
Solera LLC 
03/03/2021 
   
745,433
     
89,233
 
 
  
 
$
10,050,705
   
$
717,517
 
 
Note 11 – Capital:
Common Shares
The Fund has an unlimited amount of common shares, $0.01 par value, authorized and 18,507,502 issued and outstanding.
     
Transactions in common shares were as follows: 
 
 
 
 
Six months ended 
Year ended 
 
November 30, 2016 
May 31, 2016 
Beginning Shares 
17,729,262 
17,493,253 
Common shares issued through at-the-market offering 
701,647 
166,779 
Shares issued through dividend reinvestment 
76,593 
69,230 
Ending Shares 
18,507,502 
17,729,262 
 
On October 23, 2013, the Fund’s shelf registration allowing for delayed or continuous offering of additional shares became effective and post-effective amendments thereto became effective on October 3, 2014 and September 30, 2015. The shelf registration statement allowed for the issuance of
 

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 63


   
NOTES TO FINANCIAL STATEMENTS (Unaudited) continued 
November 30, 2016 
 
up to $150,000,000 of common shares. The Fund entered into an agreement with Cantor Fitzgerald & Co. for the sale of up to an additional 3,977,022 shares.
On November 14, 2016, the Fund’s replacement shelf registration allowing for delayed or continuous offering of additional shares became effective. The shelf registration statement allows for the issuance of up to $125,000,000 of common shares. The Fund entered into an agreement with Cantor Fitzgerald & Co. for the sale of up to an additional 3,900,000 shares.
The Adviser has paid the costs associated with the at-the-market offering of shares and will be reimbursed by the Fund up to 0.60% of the offering price of common shares sold pursuant to the shelf registration statement, not to exceed the amount of actual offering costs incurred. For the six months ended November 30, 2016, the Fund incurred $79,306 of expenses associated with the at-the market offerings.
Note 12 – Restricted Securities:
The securities below are considered illiquid and restricted under guidelines established by the Board:
Restricted Securities 
Acquisition Date 
 
Cost
   
Value
 
Airplanes Pass Through Trust 
 
           
2001-1A, 1.09% due 03/15/19 
10/14/2009 
 
$
9,732,312
   
$
3,922,308
 
Anchorage Credit Funding 1 Ltd. 
 
               
2015-1A, 6.30% due 07/28/30 
05/07/2015 
   
3,000,000
     
3,008,599
 
Capmark Military Housing Trust 
 
               
2007-AETC, 5.75% due 02/10/52 
09/18/2014 
   
1,901,466
     
1,836,943
 
Capmark Military Housing Trust 
 
               
2007-AET2, 6.06% due 10/10/52 
04/23/2015 
   
487,789
     
493,162
 
Customers Bank 
 
               
6.13% due 06/26/29 
06/24/2014 
   
2,500,000
     
2,525,000
 
EIG Investors Corp. 
 
               
10.88% due 02/01/24 
05/16/2016 
   
685,399
     
697,500
 
Fortress Credit Opportunities 
 
               
2005-1A, 0.96% due 07/15/19 
02/16/2012 
   
2,330,051
     
2,355,560
 
HP Communities LLC 
 
               
6.82% due 09/15/53 
07/21/2015 
   
974,759
     
1,054,859
 
HP Communities LLC 
 
               
6.16% due 09/15/53 
06/09/2014 
   
997,523
     
993,878
 
Pacific Beacon LLC 
 
               
5.63% due 07/15/51 
01/15/2014 
   
589,955
     
666,964
 
Turbine Engines Securitization Ltd. 
 
               
2013-1A, 6.38% due 12/13/48 
11/27/2013 
   
689,099
     
652,729
 
Schahin II Finance Co SPV Ltd 
 
               
5.88% due 09/25/22 
01/08/2014 
   
1,178,715
     
145,936
 
 
  
 
$
25,067,068
   
$
18,353,438
 
 
 

64 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
NOTES TO FINANCIAL STATEMENTS (Unaudited) continued 
November 30, 2016 
 
Note 13 – Subsequent Event:
The Fund evaluated subsequent events through the date the financial statements were available for issue and determined there were no additional material events that would require adjustment to or disclosure in the Fund’s financial statements.
 

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 65


         
SUPPLEMENTAL INFORMATION (Unaudited) 
 
November 30, 2016 
 
 
Federal Income Tax Information 
In January 2017, you will be advised on IRS Form 1099 DIV or substitute 1099 DIV as to the federal tax status of the distributions received by you in the calendar year 2016. 
 
Sector Classification 
Information in the “Schedule of Investments” is categorized by sectors using sector-level Classifications defined by the Bloomberg Industry Classification System, a widely recognized industry classification system provider. Each Fund’s registration statement has investment policies relating to concentration in specific sectors/industries. For purposes of these investment policies, the Funds usually classify sectors/industries based on industry-level Classifications used by widely recognized industry classification system providers such as Bloomberg Industry Classification System, Global Industry Classification Standards and Barclays Global Classification Scheme. 
 
Trustees 
The Trustees of the Guggenheim Strategic Opportunities Fund and their principal occupations during the past five years: 
 
 
Position(s) 
Term of Office 
 
Number of 
 
 
Held 
and Length 
 
Portfolios in 
 
Name, Address* 
with 
of Time 
Principal Occupation(s) 
Fund Complex 
Other Directorships 
and Year of Birth 
Trust 
Served** 
During Past Five Years 
Overseen 
Held by Trustees 
Independent Trustees 
 
 
 
 
Randall C. Barnes 
Trustee 
Since 2007 
Current: Private Investor (2001-present). 
98 
Current: Trustee, Purpose Investments Funds (2014-Present). 
(1951) 
 
 
 
Former: Senior Vice President and Treasurer, PepsiCo, Inc. (1993-1997); 
President, Pizza Hut International (1991-1993); Senior Vice President, Strategic Planning and New Business Development, PepsiCo, Inc. (1987-1990). 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
Donald A. 
Trustee 
Since 2014 
Current: Business broker and manager of commercial real estate, Griffith & Blair, Inc. (1997-present). 
95 
Current: Midland Care, 
Inc. (2011-present). 
Chubb, Jr. 
 
 
 
(1946 ) 
 
 
 
 
 
Jerry B. Farley 
Trustee 
Since 2014 
Current: President, Washburn University (1997-present). 
95 
Current: Westar Energy, Inc. 
(2004-present); CoreFirst Bank & Trust (2000-present). 
(1946) 
 
 
 
 
 
 
 
 
 
Roman Friedrich III 
(1946) 
Trustee and 
Chairman of 
the Contracts 
Review 
Committee 
Since 2010 
Current: Founder and Managing Partner, Roman Friedrich & Company 
(1998-present). 
95 
Current: Zincore Metals, Inc. 
(2009-present). 
 
 
 
 
Former: Senior Managing Director, MLV & Co. LLC (2010-2011). 
 
Former: Axiom Gold and Silver 
Corp. (2011-2012). 
 
 
 
 

66 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


           
SUPPLEMENTAL INFORMATION (Unaudited) continued 
 
November 30, 2016 
 
 
 
Position(s) 
Term of Office 
 
Number of 
 
 
Held 
and Length 
 
Portfolios in 
 
Name, Address* 
with 
of Time 
Principal Occupation(s) 
Fund Complex 
Other Directorships 
and Year of Birth 
Trust 
Served** 
During Past Five Years 
Overseen 
Held by Trustees 
Independent Trustees continued: 
 
 
 
 
Robert B. Karn III 
(1942) 
Trustee and 
Chairman of 
the Audit 
Committee 
Since 2010 
Current: Consultant (1998-present). 
 
Former: Arthur Andersen (1965-1997) and Managing Partner, Financial and Economic Consulting, St. Louis office (1987-1997). 
95 
Current: Peabody Energy Company 
(2003-present); GP Natural Resource 
Partners, LLC (2002- present). 
 
 
 
 
 
Ronald A. Nyberg 
(1953) 
Trustee and 
Chairman of 
the Nominating 
and Governance 
Committee 
Since 2007 
Current: Partner, Momkus McCluskey Roberts, LLC (2016-present). 
 
Former: Partner, Nyberg & Cassioppi, LLC (2000-2016); Executive Vice President, General Counsel, and Corporate Secretary, Van Kampen Investments (1982-1999). 
100 
Current: Edward-Elmhurst 
Healthcare System (2012-present). 
 
 
 
 
 
Maynard F. 
Trustee 
Since 2014 
Current: Retired. 
95 
Current: Fort Hays State University 
Foundation (1999-present); Stormont- 
Vail Foundation (2013- present); 
University of Minnesota MHA Alumni 
Philanthropy Committee (2009-present).
 
Former: Topeka Community Foundation 
(2009-2014). 
Oliverius 
 
 
 
 
(1943) 
 
 
Former: President and CEO, Stormont-Vail HealthCare (1996-2012). 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
Ronald E. 
Toupin, Jr. 
(1958) 
Trustee and 
Chairman of 
the Board 
Since 2007 
Current: Portfolio Consultant (2010-present). 
97 
Former: Bennett Group of Funds 
 
Former: Vice President, Manager and Portfolio Manager, Nuveen Asset Management (1998-1999); Vice President, Nuveen Investment Advisory Corp. (1992-1999); Vice President and Manager, Nuveen Unit Investment Trusts (1991-1999); and Assistant Vice President and Portfolio Manager, Nuveen Unit Investment Trusts (1988-1999), each of John Nuveen & Co., Inc. (1982-1999). 
 
(2011-2013). 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 67


           
SUPPLEMENTAL INFORMATION (Unaudited) continued 
 
November 30, 2016 
 
 
Position(s) 
Term of Office 
 
Number of 
 
 
Held 
and Length 
 
Portfolios in 
 
Name, Address* 
with 
of Time 
Principal Occupation(s) 
Fund Complex 
Other Directorships 
and Year of Birth 
Trust 
Served** 
During Past Five Years 
Overseen 
Held by Trustees 
Independent Trustees continued: 
 
 
 
 
Interested Trustee 
 
 
 
 
 
Donald C. 
Cacciapaglia*** 
(1951) 
President, 
Chief Executive 
Officer and 
Trustee 
Since 2012 
Current: President and CEO, certain other funds in the Fund Complex 
(2012-present); Vice Chairman, Guggenheim Investments (2010-present). 
230 
Current: Clear Spring Life Insurance 
Company (2015-present); Guggenheim Partners Investment Management Holdings LLC (2014-present); Guggenheim Partners Japan, Ltd. (2014-present); Delaware Life (2013-present); Guggenheim Life and Annuity Company (2011-present); Paragon Life Insurance Company of Indiana (2011-present). 
 
 
 
 
 
 
 
Former: Chairman and CEO, Channel Capital Group, Inc. (2002-2010). 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
The business address of each Trustee is c/o Guggenheim Investments, 227 West Monroe, Chicago, IL 60606. 
** 
This is the period for which the Trustee began serving the Fund. After a Trustee’s initial term, each Trustee is expected to serve a two-year term concurrent 
 
with the class of Trustees for which he serves: 
 
- Messrs. Farley, Karn, Nyberg, Oliverius and Toupin are Class II Trustees. Class II Trustees are expected to stand for re-election at the Fund’s annual meeting 
 
of shareholders for the fiscal year ended May 31, 2017. 
 
- Messrs. Barnes, Cacciapaglia, Chubb and Friedrich are Class I Trustees. Class I Trustees are expected to stand for re-election at the Fund’s annual meeting 
 
of shareholders for the fiscal year ended May 31, 2018. 
*** 
This Trustee is deemed to be an “interested person” of the Funds under the 1940 Act by reason of his position with the Funds’ Investment Manager and/or 
 
the parent of the Investment Manager. 
 

68 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


         
SUPPLEMENTAL INFORMATION (Unaudited) continued 
November 30, 2016 
 
 
Officers 
 
 
 
 
The Officers of the Guggenheim Strategic Opportunities Fund, who are not trustees, and their principal occupations during the past five years: 
 
 
 
Position(s) 
 
 
 
held 
Term of Office 
 
Name, Address* 
with the 
and Length of 
 
and Year of Birth 
Trust 
Time Served** 
Principal Occupations During Past Five Years 
Officers: 
 
 
 
William H. 
Belden, III 
(1965) 
 
Vice 
President 
 
 
Since 2014 
 
 
 
Current: Vice President, certain other funds in the Fund Complex (2006-present); Managing Director, Guggenheim Funds Investment Advisors, LLC (2005-present). 
 
Former: Vice President of Management, Northern Trust Global Investments (1999-2005). 
Joanna M. Catalucci 
(1966) 
 
 
 
Chief 
Compliance 
Officer 
 
 
Since 2012 
 
 
 
Current: Chief Compliance Officer, certain funds in the Fund Complex (2012-present); Senior Managing Director, Guggenheim Investments (2012-present). 
 
Former: Chief Compliance Officer and Secretary, certain other funds in the Fund Complex (2008-2012); Senior Vice President & Chief Compliance Officer, Security Investors, LLC and certain affiliates (2010-2012); Chief Compliance Officer and Senior Vice President, Rydex Advisors, LLC and certain affiliates (2010-2011). 
James M. Howley 
(1972) 
 
Assistant 
Treasurer 
 
Since 2007 
 
 
Current: Director, Guggenheim Investments (2004-present); Assistant Treasurer, certain other funds in the Fund Complex (2006-present). 
 
Former: Manager of Mutual Fund Administration, Van Kampen Investments, Inc. (1996-2004). 
Keith Kemp 
(1960) 
 
Assistant 
Treasurer 
 
Since 2016 
 
 
Current: Managing Director of Transparent Value, LLC (April 2015-present); Managing Director of Guggenheim Investments (April 2015-present) 
 
Former: Director, Transparent Value, LLC (2010-2015); Director, Guggenheim Investments (2010-2015); Chief Operating officer, Macquarie Capital Management (2007-2009). 
Amy J. Lee 
Chief Legal 
Officer 
Since 2013 
Current: Chief Legal Officer, certain other funds in the Fund Complex (2013-present); Senior Managing Director, Guggenheim Investments (2012-present). 
 
Former: Vice President, Associate General Counsel and Assistant Secretary, Security Benefit Life Insurance Company and Security Benefit Corporation (2004-2012). 
(1961) 
 
 
 
 
 
 
 
Mark E. Mathiasen 
Secretary 
Since 2008 
Current: Secretary, certain other funds in the Fund Complex (2007-present); Managing Director ,Guggenheim Investments (2007-present). 
(1978) 
 
 
 
 

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 69


           
SUPPLEMENTAL INFORMATION (Unaudited) continued 
November 30, 2016 
 
 
 
 
Name, Address* 
and Year of Birth 
Position(s) 
held 
with the 
Trust 
 
Term of Office 
and Length of 
Time Served** 
Principal Occupations During Past Five Years 
Officers continued: 
 
 
Glenn McWhinnie 
 
Assistant 
Treasurer 
Since 2016 
 
Current: Vice President, Guggenheim Investments (2009-present). 
 
Former: Tax Compliance Manager, Ernst & Young LLP (1996-2009). 
Michael P. Megaris 
 
Assistant 
Secretary 
 
Since 2014 
 
Current: Assistant Secretary, certain other funds in the Fund Complex (2014-present); Vice President, Guggenheim Investments (2012-present). 
 
Former: J.D., University of Kansas School of Law (2009-2012). 
Adam J. Nelson 
 
 
Assistant 
Treasurer 
 
 
Since 2015 
 
 
 
Current: Vice President, Guggenheim Investments (2015-present); Assistant Treasurer, certain other funds in the Fund Complex (2015-present). 
 
Former: Assistant Vice President and Fund Administration Director, State Street Corporation (2013-2015); Fund Administration Assistant Director, State Street (2011-2013); Fund Administration Manager, State Street (2009-2011). 
Kimberly J. Scott 
 
 
 
Assistant 
Treasurer 
 
 
Since 2012 
 
 
Current: Vice President, Guggenheim Investments (2012-present); Assistant Treasurer, certain other funds in the Fund Complex (2012-present). 
 
Former: Financial Reporting Manager, Invesco, Ltd. (2010-2011); Vice President/Assistant Treasurer of Mutual Fund Administration, Van Kampen Investments, Inc./Morgan Stanley Investment Management (2009-2010); Manager of Mutual Fund Administration, Van Kampen Investments, Inc./Morgan Stanley Investment Management (2005-2009). 
Bryan Stone 
 
Vice 
President 
Since 2014 
 
Current: Vice President, certain other funds in the Fund Complex (2014-present); Director, Guggenheim Investments (2013-present). 
 
Former: Senior Vice President, Neuberger Berman Group LLC (2009-2013); Vice President, Morgan Stanley (2002-2009). 
John L. Sullivan 
 
 
 
Chief 
Financial 
Officer, Chief 
Accounting 
Officer and 
Treasurer 
Since 2010 
 
 
 
Current: CFO, Chief Accounting Officer and Treasurer, certain other funds in the Fund Complex (2010-present); Senior Managing Director, Guggenheim Investments (2010-present). 
 
Former: Managing Director and CCO, each of the funds in the Van Kampen Investments fund complex (2004-2010); Managing Director and Head of Fund Accounting and Administration, Morgan Stanley Investment Management (2002-2004); CFO and Treasurer, Van Kampen Funds (1996-2004). 
 
The business address of each officer is c/o Guggenheim Investments, 227 West Monroe, Chicago, IL 60606. 
** 
Each officer serves an indefinite term, until his or her successor is duly elected and qualified. 
 

70 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
DIVIDEND REINVESTMENT PLAN (Unaudited) 
November 30, 2016 
 
Unless the registered owner of common shares elects to receive cash by contacting the Computershare Trust Company, N.A. (the “Plan Administrator”), all dividends declared on common shares of the Fund will be automatically reinvested by the Plan Administrator, Administrator for shareholders in the Fund’s Dividend Reinvestment Plan (the “Plan”), in additional common shares of the Fund. Participation in the Plan is completely voluntary and may be terminated or resumed at any time without penalty by notice if received and processed by the Plan Administrator prior to the dividend record date; otherwise such termination or resumption will be effective with respect to any subsequently declared dividend or other distribution. Some brokers may automatically elect to receive cash on your behalf and may re-invest that cash in additional common shares of the Fund for you. If you wish for all dividends declared on your common shares of the Fund to be automatically reinvested pursuant to the Plan, please contact your broker.
The Plan Administrator will open an account for each common shareholder under the Plan in the same name in which such common shareholder’s common shares are registered. Whenever the Fund declares a dividend or other distribution (together, a “Dividend”) payable in cash, non-participants in the Plan will receive cash and participants in the Plan will receive the equivalent in common shares. The common shares will be acquired by the Plan Administrator for the participants’ accounts, depending upon the circumstances described below, either (i) through receipt of additional unissued but authorized common shares from the Fund (“Newly Issued Common Shares”) or (ii) by purchase of outstanding common shares on the open market (“Open-Market Purchases”) on the New York Stock Exchange or elsewhere. If, on the payment date for any Dividend, the closing market price plus estimated brokerage commission per common share is equal to or greater than the net asset value per common share, the Plan Administrator will invest the Dividend amount in Newly Issued Common Shares on behalf of the participants. The number of Newly Issued Common Shares to be credited to each participant’s account will be determined by dividing the dollar amount of the Dividend by the net asset value per common share on the payment date; provided that, if the net asset value is less than or equal to 95% of the closing market value on the payment date, the dollar amount of the Dividend will be divided by 95% of the closing market price per common share on the payment date. If, on the payment date for any Dividend, the net asset value per common share is greater than the closing market value plus estimated brokerage commission, the Plan Administrator will invest the Dividend amount in common shares acquired on behalf of the participants in Open-Market Purchases.
If, before the Plan Administrator has completed its Open-Market Purchases, the market price per common share exceeds the net asset value per common share, the average per common share purchase price paid by the Plan Administrator may exceed the net asset value of the common shares, resulting in the acquisition of fewer common shares than if the Dividend had been paid in Newly Issued Common Shares on the Dividend payment date. Because of the foregoing difficulty with respect to Open-Market Purchases, the Plan provides that if the Plan Administrator is unable to invest the full Dividend amount in Open-Market Purchases during the purchase period or if the market discount shifts to a market premium during the purchase period, the Plan Administrator may cease making Open-Market Purchases and may invest the uninvested portion of the Dividend
 

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 71


   
DIVIDEND REINVESTMENT PLAN (Unaudited) continued 
November 30, 2016 
 
amount in Newly Issued Common Shares at net asset value per common share at the close of business on the Last Purchase Date provided that, if the net asset value is less than or equal to 95% of the then current market price per common share; the dollar amount of the Dividend will be divided by 95% of the market price on the payment date.
The Plan Administrator maintains all shareholders’ accounts in the Plan and furnishes written confirmation of all transactions in the accounts, including information needed by shareholders for tax records. Common shares in the account of each Plan participant will be held by the Plan Administrator on behalf of the Plan participant, and each shareholder proxy will include those shares purchased or received pursuant to the Plan. The Plan Administrator will forward all proxy solicitation materials to participants and vote proxies for shares held under the Plan in accordance with the instruction of the participants.
There will be no brokerage charges with respect to common shares issued directly by the Fund. However, each participant will pay a pro rata share of brokerage commission incurred in connection with Open-Market Purchases. The automatic reinvestment of Dividends will not relieve participants of any Federal, state or local income tax that may be payable (or required to be withheld) on such Dividends.
The Fund reserves the right to amend or terminate the Plan. There is no direct service charge to participants with regard to purchases in the Plan; however, the Fund reserves the right to amend the Plan to include a service charge payable by the participants.
All correspondence or questions concerning the Plan should be directed to the Plan Administrator, Computershare Trust Company, N.A., P.O. Box 30170, College Station, TX 77842-3170; Attention: Shareholder Services Department, Phone Number: (866) 488-3559 or online at www.computershare.com/investor.
 

72 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT


   
FUND INFORMATION 
November 30, 2016 
 
Board of Trustees 
Investment Adviser 
Randall C. Barnes 
Guggenheim Funds Investment 
 
Advisors, LLC 
Donald C. Cacciapaglia* 
Chicago, IL 
 
Donald A. Chubb Jr. 
 
 
Investment Sub-Adviser 
Jerry B. Farley 
Guggenheim Partners Investment 
 
Management, LLC 
Roman Friedrich III 
Santa Monica, CA 
   
Robert B. Karn III 
Administrator & Accounting Agent 
 
MUFG Investor Services (US), LLC 
Ronald A. Nyberg 
Rockville, MD 
   
Maynard F. Oliverius 
Custodian 
 
The Bank of New York Mellon Corp 
Ronald E. Toupin, Jr., 
New York, NY 
Chairperson 
 
 
Legal Counsel 
* Trustee is an “interested person” (as defined 
Skadden, Arps, Slate, 
in section 2(a)(19) of the 1940 Act) 
Meagher & Flom LLP 
(“Interested Trustee”) of the Trust because of 
New York, NY 
his position as the President and CEO of the 
Investment Adviser and Sub-Adviser. 
Independent Registered Public 
 
Accounting Firm 
Principal Executive Officers 
Ernst & Young LLP 
 
McLean, VA 
Donald C. Cacciapaglia 
 
President and Chief Executive Officer 
 
Joanna M. Catalucci 
Chief Compliance Officer 
 
Amy J. Lee 
 
Chief Legal Officer 
 
 
Mark E. Mathiasen 
 
Secretary 
 
 
John L. Sullivan 
 
Chief Financial Officer, Chief Accounting 
 
Officer and Treasurer 
 
 

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 73


   
FUND INFORMATION continued 
November 30, 2016 
 
Privacy Principles of the Fund
The Fund is committed to maintaining the privacy of its shareholders and to safeguarding their non-public personal information. The following information is provided to help you understand what personal information the Fund collects, how the Fund protects that information and why, in certain cases, the Fund may share information with select other parties.
Generally, the Fund does not receive any non-public personal information relating to its shareholders, although certain non-public personal information of its shareholders may become available to the Fund. The Fund does not disclose any non-public personal information about its shareholders or former shareholders to anyone, except as permitted by law or as is necessary in order to service shareholder accounts (for example, to a transfer agent or third party administrator).
The Fund restricts access to non-public personal information about its shareholders to employees of the Fund’s investment advisor and its affiliates with a legitimate business need for the information. The Fund maintains physical, electronic and procedural safeguards designed to protect the non-public personal information of its shareholders.
Questions concerning your shares of Guggenheim Strategic Opportunities Fund? 
•  If your shares are held in a Brokerage Account, contact your Broker. 
•  If you have physical possession of your shares in certificate form, contact the Fund’s Transfer Agent: 
Computershare Trust Company, N.A., P.O. Box 30170, College Station, TX 77842-3170; (866) 488-3559 or online 
at www.computershare.com/investor. 
 
This report is sent to shareholders of Guggenheim Strategic Opportunities Fund for their information. It is not a Prospectus, circular or representation intended for use in the purchase or sale of shares of the Fund or of any securities mentioned in this report.
A description of the Fund’s proxy voting policies and procedures related to portfolio securities is available without charge, upon request, by calling the Fund at (800)345-7999.
Information regarding how the Fund voted proxies for portfolio securities, if applicable, during the most recent 12-month period ended June 30, is also available, without charge and upon request by calling (800)345-7999, by visiting the Fund’s website at guggenheiminvestments.com/gof or by accessing the Fund’s Form N-PX on the U.S. Securities and Exchange Commission’s (SEC) website at www.sec.gov.
The Fund files its complete schedule of portfolio holdings with the SEC for the first and third quarters of each fiscal year on Form N-Q. The Fund’s Form N-Q is available on the SEC website at www.sec.gov or by visiting the Fund’s website at guggenheiminvestments.com/gof. The Fund’s Form N-Q may also be viewed and copied at the SEC’s Public Reference Room in Washington, DC; information on the operation of the Public Reference Room may be obtained by calling (800) SEC-0330 or at www.sec.gov.
Notice to Shareholders
Notice is hereby given in accordance with Section 23(c) of the Investment Company Act of 1940, as amended, that the Fund from time to time may purchase shares of its common stock in the open market.
 

74 l GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT

 
This Page Intentionally Left Blank.
 

GOF l GUGGENHEIM STRATEGIC OPPORTUNITIES FUND SEMIANNUAL REPORT l 75



ABOUT THE FUND MANAGERS
Guggenheim Partners Investment Management, LLC
Guggenheim Partners Investment Management, LLC (“GPIM”) is an indirect subsidiary of Guggenheim Partners, LLC, a diversified financial services firm. The firm provides capital markets services, portfolio and risk management expertise, wealth management, and investment advisory services. Clients of Guggenheim Partners, LLC subsidiaries are an elite mix of individuals, family offices, endowments, foundations, insurance companies and other institutions.
Investment Philosophy
GPIM’s investment philosophy is predicated upon the belief that thorough research and independent thought are rewarded with performance that has the potential to outperform benchmark indexes with both lower volatility and lower correlation of returns over time as compared to such benchmark indexes.
Investment Process
GPIM’s investment process is a collaborative effort between various groups including the Portfolio Construction Group, which utilize proprietary portfolio construction and risk modeling tools to determine allocation of assets among a variety of sectors, and its Sector Specialists, who are responsible for security selection within these sectors and for implementing securities transactions, including the structuring of certain securities directly with the issuers or with investment banks and dealers involved in the origination of such securities.
 
Guggenheim Funds Distributors, LLC
227 West Monroe Street
Chicago, IL 60606
Member FINRA/SIPC
(01/17)
 
NOT FDIC-INSURED l NOT BANK-GUARANTEED l MAY LOSE VALUE
 
CEF-GOF-SAR-1116
 

 
Item 2.  Code of Ethics.
Not applicable for a semi-annual reporting period.
Item 3.  Audit Committee Financial Expert.
Not applicable for a semi-annual reporting period.
Item 4.  Principal Accountant Fees and Services.
Not applicable for a semi-annual reporting period.
Item 5.  Audit Committee of Listed Registrants.
Not applicable for a semi-annual reporting period.
Item 6.  Schedule of Investments.
The Schedule of Investments is included as part of Item 1.
Item 7.  Disclosure of Proxy Voting Policies and Procedures for Closed-End Management Investment Companies.
Not applicable for a semi-annual reporting period.
Item 8.  Portfolio Managers of Closed-End Management Investment Companies.
(a) Not applicable for a semi-annual reporting period.
(b) As of January 30, 2017, Steven Brown has been added as Portfolio Manager of the registrant. Please see the information below as required by paragraphs (a)(1) - (a)(4) of this Item 8 as of November 30, 2016 for Steven Brown.
(a)(1)  Guggenheim Partners Investment Management, LLC (“Guggenheim”) serves as the investment sub-adviser for the registrant and is responsible for the day-to-day management of the registrant’s portfolio. Guggenheim uses a team approach to manage client portfolios.  Day to day management of a client portfolio is conducted under the auspices of Guggenheim’s Portfolio Construction Group (“PCG”).  PCG’s members include the Chief Investment Officer (“CIO”) and other key investment personnel.  The PCG, in consultation with the CIO, provides direction for overall investment strategy.  The PCG performs several duties as it relates to client portfolios including: determining both tactical and strategic asset allocations; and monitoring portfolio adherence to asset allocation targets; providing sector specialists with direction for overall investment strategy, which may include portfolio design and the rebalancing of portfolios; performing risk management oversight; assisting sector managers and research staff in determining the relative valuation of market sectors; and providing a forum for the regular discussion of the economy and the financial markets to enhance the robustness of Guggenheim’s strategic and tactical policy directives.

Steven Brown shares primary responsibility for the day-to-day management of the registrant’s portfolio and his information is provided as of November 30, 2016:

Name
 
Since
Professional Experience During the Last Five Years
Steven Brown
2017
 
Guggenheim Partners Investment Management, LLC, Managing Director and Portfolio Manager – 2016 – Present; Guggenheim Partners Investment Management, LLC, Director – 2014 – 2016; Guggenheim Partners Investment Management, LLC, Vice President 2013-2014; Guggenheim Partners Investment Management, LLC, Senior Associate 2012-2013.

(a)(2)(i-iii) Other Accounts Managed by the Portfolio Managers
 
The following table summarizes information regarding each of the other accounts managed by Steven Brown as of November 30, 2016:

Steven Brown:
                 
Type of Account
 
Number of Accounts
 
Total Assets in the Accounts
 
Number of Accounts In Which the Advisory Fee is Based on Performance
 
 
Total Assets in the Accounts In Which the Advisory Fee is Based on Performance
Registered investment companies
 
 
13
 
11,344,634,630
 
0
 
$0
Other pooled investment vehicles
 
 
5
 
$4,186,499,620
 
2
 
$3,453,576,507
Other accounts
 
 
11
 
$1,987,712,964
 
4
 
$615,551,831


(a)(2)(iv) Potential Conflicts of Interest

Actual or apparent conflicts of interest may arise when a portfolio manager has day-to-day management responsibilities with respect to more than one fund or other account. More specifically, portfolio managers who manage multiple funds and/or other accounts may be presented with one or more of the following potential conflicts.

The management of multiple funds and/or other accounts may result in a portfolio manager devoting unequal time and attention to the management of each fund and/or other account. Guggenheim seeks to manage such competing interests for the time and attention of a portfolio manager by having the portfolio manager focus on a particular investment discipline. Specifically, the ultimate decision maker for security selection for each client portfolio is the Sector Specialist Portfolio Manager.  They are responsible for analyzing and selecting specific securities that they believe best reflect the risk and return level as provided in each client’s investment guidelines.

Guggenheim may have clients with similar investment strategies.  As a result, if an investment opportunity would be appropriate for more than one client, Guggenheim may be required to choose among those clients in allocating such opportunity, or to allocate less of such opportunity to a client than it would ideally allocate if it did not have to allocate to multiple clients.  In addition, Guggenheim may determine that an investment opportunity is appropriate for a particular account, but not for another.

Allocation decisions are made in accordance with the investment objectives, guidelines, and restrictions governing the respective clients and in a manner that will not unfairly favor one client over another. Guggenheim’s allocation policy provides that investment decisions must never be based upon account performance or fee structure.  Accordingly, Guggenheim’s allocation procedures are designed to ensure that investment opportunities are allocated equitably among different client accounts over time.  The procedures also seek to ensure reasonable efficiency in client transactions and to provide portfolio managers with flexibility to use allocation methodologies appropriate to Guggenheim’s investment disciplines and the specific goals and objectives of each client account.

In order to minimize execution costs and obtain best execution for clients, trades in the same security transacted on behalf of more than one client may be aggregated.  In the event trades are aggregated, Guggenheim’s policy and procedures provide as follows: (i) treat all participating client accounts fairly; (ii) continue to seek best execution; (iii) ensure that clients who participate in an aggregated order will participate at the average share price with all transaction costs shared on a pro-rata basis based on each client’s participation in the transaction; (iv) disclose its aggregation policy to clients.

Guggenheim, as a fiduciary to its clients, considers numerous factors in arranging for the purchase and sale of clients’ portfolio securities in order to achieve best execution for its clients.  When selecting a broker, individuals making trades on behalf of Guggenheim clients consider the full range and quality of a broker’s services, including execution capability, commission rate, price, financial stability and reliability.  Guggenheim is not obliged to merely get the lowest price or commission but also must determine whether the transaction represents the best qualitative execution for the account.

In the event that multiple broker/dealers make a market in a particular security, Guggenheim’s Portfolio Managers are responsible for selecting the broker-dealer to use with respect to executing the transaction.  The broker-dealer will be selected on the basis of how the transaction can be executed to achieve the most favorable execution for the client under the circumstances.  In many instances, there may only be one counter-party active in a particular security at a given time.  In such situations the Employee executing the trade will use his/her best effort to obtain the best execution from the counter-party.

Guggenheim and the registrant have adopted certain compliance procedures which are designed to address these types of conflicts. However, there is no guarantee that such procedures will detect each and every situation in which a conflict arises.

(a)(3) Portfolio Manager Compensation

Guggenheim compensates portfolio management staff for their management of the registrant’s portfolio. Compensation is evaluated based on their contribution to investment performance relative to pertinent benchmarks and qualitatively based on factors such as teamwork and client service efforts.  Guggenheim’s staff incentives may include: a competitive base salary, bonus determined by individual and firm wide performance, equity participation, and participation opportunities in various Guggenheim investments.  All Guggenheim employees are also eligible to participate in a 401(k) plan to which Guggenheim may make a discretionary match after the completion of each plan year.

(a)(4) Portfolio Securities Ownership

The following table discloses the dollar range of equity securities of the registrant beneficially owned by Steven Brown as of November 30, 2016:

Name of Portfolio Manager
Dollar Amount of Equity Securities in Registrant
Steven Brown
$-0-

Item 9.  Purchases of Equity Securities by Closed-End Management Investment Company and Affiliated Purchasers.
None.
Item 10.  Submission of Matters to a Vote of Security Holders.
The registrant has not made any material changes to the procedures by which shareholders may recommend nominees to the registrant’s Board of Trustees.
Item 11.  Controls and Procedures.
(a)      The registrant's principal executive officer and principal financial officer have evaluated the registrant's disclosure controls and procedures (as defined in Rule 30a-3(c) under the Investment Company Act) as of a date within 90 days of this filing and have concluded based on such evaluation, as required by Rule 30a-3(b) under the Investment Company Act, that the registrant's disclosure controls and procedures were effective, as of that date, in ensuring that information required to be disclosed by the registrant in this Form N-CSR was recorded, processed, summarized, and reported within the time periods specified in the Securities and Exchange Commission’s rules and forms.
(b)      There were no changes in the registrant’s internal control over financial reporting (as defined in Rule 30a-3(d) under the Investment Company Act) that occurred during the registrant’s second fiscal quarter of the period covered by this report that have materially affected, or are reasonably likely to materially affect, the registrant’s internal control over financial reporting.

Item 12.  Exhibits.
(a)(1)   Not applicable.
(a)(2)   Certifications of principal executive officer and principal financial officer pursuant to Rule 30a-2(a) of the Investment Company Act.
(a)(3)   Not applicable.
(b)       Certifications of principal executive officer and principal financial officer pursuant to Rule 30a-2(b) under the Investment Company Act and Section 906 of the Sarbanes-Oxley Act of 2002.


SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934 and the Investment Company Act of 1940, the registrant has duly caused this report to be signed on its behalf by the undersigned, thereunto duly authorized.
Guggenheim Strategic Opportunities Fund
By:      /s/ Donald C. Cacciapaglia
Name:  Donald C. Cacciapaglia
Title:     President and Chief Executive Officer
Date:    February 6, 2017
Pursuant to the requirements of the Securities Exchange Act of 1934 and the Investment Company Act of 1940, this report has been signed by the following persons on behalf of the registrant and in the capacities and on the dates indicated.
By:         /s/ Donald C. Cacciapaglia
Name:    Donald C. Cacciapaglia
Title:       President and Chief Executive Officer
Date:      February 6, 2017
By:         /s/ John L. Sullivan
Name:    John L. Sullivan
Title:      Chief Financial Officer, Chief Accounting Officer and Treasurer
Date:     February 6, 2017