By The Structured Team —

At the tender age of 10 years old, Windows 10 is over the hill. Microsoft is ending support for this stalwart desktop OS on Oct. 14, 2025.

If you haven’t already done so, now is definitely the time to get your organization’s upgrade plan in motion for any devices that are not yet running Windows 11. And just maybe keep in mind that Windows 12 is on the horizon. (Rumor has it that Windows 12 will have deep AI integration and may require significant RAM and processing power, with a neural processing unit [NPU] required to unlock the OS’s full functionality.)

Wait – What Does ‘Windows 10 End of Support’ Mean?

First, it is important to understand what Microsoft means by “end of support.” It does not mean that on Oct. 15, all laptops, desktops, and similar end-user devices will encounter a bluescreen error and become unusable.

What it does mean, however, is that these devices will become inherently less secure. Microsoft will cease software updates, security updates or fixes, and will not offer technical support for any issue. This is a detriment to your overall security posture, which increases your risk and could have ramifications for your regulatory compliance adherence and cybersecurity insurance.

Best not to risk it and instead act sooner rather than later. Read on to learn how.

Assessing and Upgrading: Your 6-Step Game Plan

Upgrading to Windows 11 isn’t something you just wing — it’s more like planning a big family road trip. You need to check your car, pack the essentials, and have a plan for when someone inevitably asks, “Are we there yet?”

This section breaks down how to assess your current setup and make the switch to Windows 11, with practical steps and a few extra tips to keep things smooth and secure for IT admins and business leaders alike. No tech wizardry required — just solid prep and a little know-how.

1. Check Your Hardware’s Readiness (It’s Picky for a Reason)

Windows 11 has some specific hardware demands, and it’s not just being fussy — it’s about keeping your system secure and snappy. Two biggies are TPM 2.0 (Trusted Platform Module) and Secure Boot. TPM 2.0 is like a vault for your encryption keys, protecting sensitive data, while Secure Boot acts like a gatekeeper, ensuring only legit software starts up your device. Without these, Windows 11 wouldn’t even say hello.

• How to Check: Download Microsoft’s PC Health Check tool — it’s free, fast and tells you if your devices pass the vibe check. It’ll flag any hardware that’s not up to snuff, like an old processor or missing TPM.
  
  
• Extra Tip: If some machines don’t qualify, don’t sweat it. You might consider a hardware refresh for those stragglers or explore Windows 365, which lets you run Windows 11 in the cloud — no fancy hardware required. Think of it as a sneaky way to future-proof without breaking the bank.
  
  
• One More Thing: If you haven’t already done so, migration is a great time to begin inventory management with asset tagging and warranty/support tracking. It also presents a good opportunity to establish hardware refresh cycles and secure disposal procedures, which may include either trading in old devices or recycling them.

2. Seize the Chance to Focus on Cybersecurity

Stronger protections inherent in Windows 11, like hardware-based isolation, Secure Boot, and TPM 2.0, help prevent malware and unauthorized access, significantly reducing the attack surface compared to Windows 10. But in addition to an OS upgrade, this migration process also presents a good opportunity to focus more broadly on securing your endpoints with best practices.

• How to Do It:  Additional ways to improve your security posture are to:
  • Enforce multifactor authentication (MFA) for access to all corporate resources,
  • Ensure all laptops have full disk encryption enabled to protect data at rest,
  • Establish and automate a device and OS patch management practice,
  • Enable remote wipe and lock functionality for lost or stolen devices, and
  • Embed enterprise-grade antivirus and endpoint detection and response (EDR) tools like Microsoft Defender for Endpoint.
    
    
• Extra Tip: You may also want to take your security practices even further and leverage the SIEM/SOAR functionality of Microsoft Sentinel.

3. Make Sure Your Apps Are Along for the Ride

Your applications are the MVPs of your workday, so you need to know they’ll work with Windows 11. Most modern software should be fine, but there’s always that one quirky program that could throw a tantrum.

• How to Check: If your business uses Microsoft Intune, it’s a great way to list all your apps and spot any potential troublemakers. No Intune? The Windows 11 Compatibility Checker or even third-party tools like Flexera’s AdminStudio can give you the rundown.
  
  
• Extra Tip: Don’t just trust the tools — test your key apps in a safe space first. Set up a spare machine or a virtual “sandbox” to see how they behave on Windows 11. This way, you avoid the chaos of a critical app crashing mid-upgrade. Bonus points if you jot down which apps need updates or replacements before you start.

4. Roll It Out Smart (Because Slow and Steady Wins)

Jumping everyone to Windows 11 at once is a recipe for headaches. Instead, think of it like rolling out a new coffee blend in the office — start with a small group, see how it goes, then bring it to the masses.

• How to Do It: Tools like Microsoft Intune let you push the upgrade to specific teams or departments over time. For an even slicker process, Windows Autopilot can set up devices automatically, saving you from manually configuring every laptop.

• Extra Tip: Map out a game plan. Pick a pilot group — like your IT folks or a tech-savvy team — to test the waters. Give them a week or two, gather their feedback, and tweak your approach. Oh, and communicate! Let your team know what’s coming with a quick email, a short training session, or even a cheat sheet on cool new features (hello, Snap Layouts). It is also a good idea to include the “why” in your communication with end users. When people understand why change is being thrust upon them, especially when it involves something as important as their work device, they are better equipped to adapt.  Happy, informed users make for a smoother rollout.
  
  
• One More Thing: Get buy-in from the top — finance, ops, HR, whomever has critical visibility, access and uptime requirements. A quick heads-up keeps everyone aligned and avoids angry conversations about last-minute surprises.

5. Back Up Before You Leap

This isn’t technically part of the upgrade, but it’s a must-do. Think of it like packing an emergency kit — you hope you don’t need it, but you’ll be glad it’s there if something goes wonky.

• How to Do It: Use Microsoft Azure Backup if you’re in the Microsoft ecosystem or stick with whatever backup solution you trust. Just make sure all your critical files —documents, databases, that spreadsheet of coffee orders — are safe before you hit “upgrade.”

• Extra Tip: Double-check that your backups actually work. Run a quick restore test on a small file to confirm you’re not banking on a dud.

6. Post-Migration Monitoring

Make sure time is scheduled for post-migration monitoring and optimization to ensure that all systems, applications, and user profiles are functioning correctly and securely in the new environment. These audits help identify and resolve any compatibility issues, configuration errors, or security vulnerabilities that may have been introduced during the upgrade process. Additionally, they provide valuable insights and documentation that can inform future upgrades and support compliance with organizational and regulatory standards.

• How to Do It: Use Microsoft’s tools to track system and health performance, select a point person to collect feedback from users, and delegate time and resources to make needed adjustments based on real-world usage.
  
• Extra Tip: As mentioned earlier, before the first device is updated, make sure every affected user understands the timeline for what is happening, what they can expect to experience, and knows the support number to call or text for post-migration help.

By following the process above, your enterprise shift to Windows 11 should be as calm and stable as any significant migration can be. But don’t get overly complacent and wait until October to act. This migration could still require a great deal of time and energy — especially if you have a lot of older devices and legacy apps running on your network.

Final Thoughts on Windows 10 End of Support

As Windows 10 end of support approaches, organizations must act decisively to ensure business continuity, security and productivity.

Migrating to Windows 11 is not just a technical upgrade — it’s a strategic opportunity to modernize IT infrastructure, enhance user experiences and strengthen cybersecurity. By following best practices such as conducting thorough hardware assessments, mapping your apps, carefully planning rollouts, and leveraging tools like Microsoft Intune or Windows Autopilot, organizations can streamline the transition and minimize disruptions.

As with everything, early planning and proactive communication with stakeholders are key to a successful migration.

Need Help Navigating the Transition?

As a trusted Microsoft Solutions Partner with partner designations in Security, Azure, and Data & AI, we offer:

• Migration assessments
• Security workshops
• Azure readiness evaluations
• AI and data modernization roadmaps

Let’s turn this challenge into a strategic advantage. Together, we’ll build a secure, intelligent and future-ready workplace.