Chicago, IL – With Microsoft officially ending support for Windows 10 on October 14, 2025, businesses across Chicago and surrounding areas face an important IT transition. After this deadline, Windows 10 systems will no longer receive security updates or support, increasing the risk of cybersecurity vulnerabilities, regulatory compliance issues, and operational disruptions.
Why the Windows 10 End-of-Life Matters
When an operating system reaches End-of-Life (EOL), it means Microsoft will no longer release security patches, bug fixes, or technical support. For businesses still running Windows 10 after October 2025, this can lead to:
- Increased cybersecurity risks – Unpatched vulnerabilities could be exploited by cybercriminals.
- Regulatory compliance issues – Businesses in healthcare, finance, and other industries may face penalties for running unsupported systems.
- System performance decline – Outdated software can lead to slowdowns, crashes, and compatibility issues with new applications.
- Higher IT maintenance costs – Keeping old systems running often becomes more expensive than upgrading.
To help businesses navigate this transition effectively, Computerease IT Support of Chicago has developed a Windows 10 Migration Plan with key steps to ensure a smooth, secure upgrade.
How to Plan the Windows 10 Migration
Transitioning from Windows 10 requires careful planning and execution to avoid business disruptions. Below is a step-by-step migration checklist to help businesses prepare:
1. Conduct an IT Asset Inventory
- Identify all computers, servers, and devices running Windows 10.
- Determine which applications and software require updates or replacements.
- Check for hardware compatibility with newer Windows versions.
2. Assess Business Needs & Compliance Requirements
- Review industry-specific regulations (e.g., HIPAA, PCI-DSS) that may require immediate upgrades.
- Evaluate whether Windows 11 or alternative solutions (such as cloud-based systems) better fit the business needs.
3. Develop a Migration Timeline
- Prioritize critical systems that need upgrading first.
- Plan upgrades during off-peak hours to minimize downtime.
- Allocate budget and resources for hardware/software updates.
4. Backup & Secure Business Data
- Implement full system backups before making changes.
- Verify that backups are secure and accessible in case of migration issues.
- Ensure a disaster recovery plan is in place.
5. Test Upgrades in a Controlled Environment
- Run pilot upgrades on a few devices before a full rollout.
- Test software and business applications for compatibility.
- Train employees on new system features and workflows.
6. Deploy & Monitor the New System
- Schedule upgrades in phases to minimize disruptions.
- Monitor for technical issues and security vulnerabilities post-migration.
- Adjust IT policies and procedures to align with new system capabilities.
Additional Considerations for Chicago Businesses
For businesses in Chicago’s financial, healthcare, and manufacturing sectors, compliance and cybersecurity should be top priorities during this transition. Legacy systems running Windows 10 may become an easy target for cybercriminals, making proactive IT planning essential.
Businesses should also consider whether a hybrid or fully cloud-based infrastructure could improve security, remote access, and cost efficiency.
Next Steps
The Windows 10 EOL deadline may seem distant, but upgrading IT infrastructure takes time and strategic planning. Businesses are encouraged to begin assessments now to avoid last-minute disruptions.
For additional resources on planning a Windows 10 migration, visit:
www.computer-service.com/win10-eol
About Computerease IT Support of Chicago
Computerease IT Support of Chicago is a trusted IT services provider specializing in cybersecurity, managed IT, and cloud solutions. As a Microsoft Certified Partner, the company helps businesses implement secure, efficient IT strategies that align with compliance and security best practices.
Preparing Chicago businesses for a secure, post-Windows 10 future.
Media Contact
Name
Computerease IT Support of Chicago
Contact name
Ryan Haislar
Contact phone
312-463-4646
Contact address
200 West Madison, Suite 2100
City
Chicago
State
IL
Zip
60606
Country
United States
Url
https://www.computer-service.com/
