Technology should empower your business—not leave it vulnerable to outdated systems and security threats.
But on 14 October 2025, Windows 10 will reach end of support (EOS), meaning no more security patches, bug fixes, or Microsoft support.
For IT leaders, this transition is more than just maintaining operations. It is an opportunity to strengthen security, modernise infrastructure, and boost productivity. The focus is not on whether to act, but on ensuring a seamless and cost-effective transition.
This checklist provides a structured roadmap to help you prepare, migrate, and optimise your IT environment. Whether you’re upgrading to Windows 11, implementing cloud solutions, or refining your long-term IT strategy, now is the time to act before EOS causes disruption.
Step 1. Assess your IT environment
Before upgrading, IT teams must evaluate their IT infrastructure to identify upgrade-ready devices, prioritise replacements, and allocate resources efficiently. A thorough assessment ensures the migration is cost-effective, well-organised, and aligned with operational needs, reducing last-minute expenses or security risks. Key steps in this assessment include:
- Audit all Windows 10 devices: Identify all PCs, laptops, and workstations still running Windows 10.
- Evaluate hardware compatibility: Use Microsoft's to confirm if devices meet Windows 11 system requirements.
Categorise devices based on upgrade readiness:
- Upgrade-ready: Meets Windows 11 requirements and can be upgraded immediately.
- Needs hardware enhancements: Falls short of requirements but can be upgraded with RAM, storage, or firmware updates. Assess if upgrading is more cost-effective than replacing.
- Requires replacement: Cannot meet Windows 11 requirements even with upgrades. Plan for phased replacement.
Step 2. Check software & application compatibility
Ensuring business-critical applications remain functional on Windows 11 is key to a smooth migration. Addressing compatibility issues in advance prevents security risks, system failures, and productivity loss.
To ensure all critical applications function properly after migration, IT teams should:
- Test software compatibility: Use Microsoft Compatibility Appraiser to identify applications that may need upgrades.
- Check third-party integrations: Ensure security software, automation scripts, and productivity apps are compatible.
- Plan for legacy software – if needed:
- Upgrade to a Windows 11-compatible version.
- Use virtualisation solutions (Citrix, VMware) for applications that cannot be replaced immediately.
For organisations with limited in-house IT resources, navigating application compatibility can be complex and time-consuming. Schedule a consultation with The Missing Link to ensure a seamless transition, from compatibility assessments to handling application updates and optimising your IT environment.
Step 3. Back up business-critical data
A well-executed backup strategy protects critical business data during migration. Without it, IT teams risk losing system configurations, applications, or sensitive files.
To minimise risk and ensure data integrity, IT teams should:
- Implement a 3-2-1 backup strategy: Three copies, two different storage types, one off-site.
- Use cloud-based backup solutions: Ensure OneDrive, Microsoft 365, or enterprise storage solutions are enabled.
- Test backup restoration: Run a data recovery test before migration to verify data integrity.
Step 4. Plan your budget & migration timeline
Strategic budgeting and timeline planning ensure a smooth, cost-effective transition. Early preparation prevents unexpected costs, resource shortages, and operational disruptions. Leveraging OEM trade-in and recycling programs can also optimise hardware costs while supporting sustainability initiatives.
Key steps in migration planning:
- Validate data migration: Confirm that files, system settings, and configurations have been securely transferred.
- Assess system readiness: Ensure Active Directory, Mobile Device Management (MDM), and Virtual Desktop setups are aligned with business needs.
- Confirm phased deployment structure: Align rollout phases with business priorities and test critical workflows before full deployment.
By combining financial planning with final migration validation, IT teams can execute a smooth, cost-effective Windows 11 transition.
Step 5. Deploy Windows 11 in phases
A structured rollout allows IT teams to identify compatibility issues early, optimise system settings, and ensure user readiness before full deployment.
Key steps to ensure a seamless transition:
- Phase 1: Pilot deployment: Deploy Windows 11 to a test group to assess performance and compatibility.
- Phase 2: Expand rollout: Upgrade non-critical systems, resolving any issues before full deployment.
- Phase 3: Full deployment: Complete the upgrade across essential business operations once stability is confirmed.
Additional best practices:
- Monitor system performance for 48–72 hours post-upgrade to track security, application stability, and user feedback.
- Train employees on new features and updated security policies to ensure a smooth transition.
With a phased approach, businesses can mitigate disruptions and ensure a stable, user-ready migration to Windows 11.
Step 6: Optimise & secure Windows 11 post-migration
Ensuring long-term security, performance, and compliance after deployment is critical to maintaining a stable and resilient IT environment. Strengthening security controls protects business data, while ongoing monitoring and optimisation help reduce inefficiencies and minimise cyber risks.
To maintain a secure and optimised Windows 11 environment, IT teams should:
- Implement security policies: Enforce Zero Trust security, Multi-Factor Authentication (MFA), and endpoint protection.
- Optimise performance settings: Configure power settings, system updates, and IT management policies.
- Review compliance requirements: Ensure Windows 11 aligns with ISO 27001, Essential Eight, and industry regulations.
Step 7: Decommission Windows 10 securely
Proper decommissioning removes security risks, prevents unauthorised access to sensitive data, and ensures compliance with industry regulations. IT teams must follow secure disposal practices to protect business information and support sustainability initiatives.
Key steps to securely retire outdated Windows 10 devices:
- Wipe and encrypt old devices: Use secure data erasure tools before disposal.
- Dispose of outdated hardware responsibly: Participate in e-waste recycling programs.
- Validate final compliance checks: Ensure all retired devices meet regulatory and security requirements.
Step 8: Post-migration support & contingency planning
After deployment, IT teams must monitor system performance, address unexpected issues, and refine configurations to ensure business continuity.
Key steps for effective post-migration support:
- Provide IT helpdesk support: Ensure users have access to technical support for troubleshooting and adoption challenges.
- Monitor system performance for 30–90 days: Track network stability, software functionality, and security logs.
- Implement a rollback strategy: Have contingency measures in place for critical failures.
- Refine workflows and access controls: Adjust IT management settings based on real-time feedback.
Act now: Secure your Windows 10 migration with The Missing Link
The end of support for Windows 10 is fast approaching, and failing to upgrade in time can leave your business vulnerable to security risks, compliance violations, and operational downtime.
The Missing Link ensures a seamless, secure migration with:
- Comprehensive IT audits: Identifying upgrade paths, hardware requirements, and security risks.
- Phased deployment strategies: Minimising downtime while ensuring business continuity.
- Security-first approach: Aligning with Essential Eight, ISO 27001, and industry compliance standards.
Need expert guidance? From hardware readiness assessments to application compatibility testing, deployment planning, and ongoing support, our Windows 10 end of support services provide end-to-end migration solutions tailored to your business.
Get in touch with us today.
