The clock is ticking for Windows 10. Microsoft has officially marked October 14, 2025, as the end-of-life date for the beloved OS. That might sound like a distant deadline, but in IT terms, it’s right around the corner. If your organization hasn’t started planning for Windows 11, now’s the time to get moving.

Let’s talk about what end-of-life means, why you can’t ignore it, and how to make the jump to Windows 11 without losing your mind (or your weekends).

 

What Does End-of-Life Mean for Windows 10?

When Windows 10 hits its expiration date, here’s what you’ll lose:

  • No more security updates: Vulnerabilities won’t get patched, leaving your systems exposed.
  • No feature updates: Windows 10 will stagnate while the rest of the tech world moves forward.
  • No official support: You’re on your own for troubleshooting and compliance issues.

Running an unsupported OS isn’t just risky—it’s a compliance and security nightmare. For most businesses, staying on Windows 10 past 2025 simply isn’t an option.

 

Why Upgrade to Windows 11?

Windows 11 isn’t just a cosmetic refresh. It’s built for the modern workplace, focusing on security, productivity, and future-proofing. Here’s why it’s worth the move:

  • Zero Trust Security: Features like TPM 2.0, Virtualization-Based Security (VBS), and hardware root-of-trust support make it a fortress for modern threats.
  • Productivity Enhancements: Snap Layouts, better multi-monitor support, and Teams integration help users work smarter, not harder.
  • Hybrid Work Ready: Optimized for cloud environments, Windows 11 is built with hybrid and remote work in mind.
  • Long-Term Support: Sticking with Windows 10 means falling further behind, while Windows 11 positions your organization for what’s next.

 

Planning Your Windows 11 Upgrade

The move to Windows 11 doesn’t have to be chaotic. Here’s a step-by-step approach to keep things smooth:

 

1. Assess Your Hardware

Windows 11 has stricter requirements than its predecessor (hello, TPM 2.0). Start by auditing your current hardware to see what’s compatible.

Use Intune for a Hardware Assessment

  • Navigate to Endpoint Analytics in Intune.
  • Check the Work From Anywhere report to identify devices that are Windows 11 ready.

Tip: Devices that don’t meet the requirements may need upgrading or replacing—start budgeting early.

 

2. Test the New OS

Don’t roll out Windows 11 to everyone at once. Test it with a small group of users first (preferably IT and power users). Use their feedback to refine your deployment strategy.

 

3. Leverage Intune for Deployment

If you’re managing your environment with Intune, upgrading to Windows 11 is straightforward. Use Windows Update for Business to deploy feature updates in a controlled manner:

  1. Go to Devices > Windows > Feature Updates.
  2. Create a new policy targeting Windows 11 24H2 or the latest version.
  3. Assign the policy to Azure AD groups.

 

Pro Tip: Use Update Rings to stagger the rollout and test updates before pushing them to all users.

 

 

4. Train Your Users

Even minor interface changes can confuse users. Prepare your teams with:

  • Short training sessions on Windows 11’s new features.
  • Guides or videos highlighting productivity boosters like Snap Layouts and Teams integration.

 

Overcoming Common Objections

Some users (or even IT admins) might resist the change. Here’s how to address the usual pushback:

  • “We need to test everything before upgrading.”
    Sure, but Windows 11 is part of an evergreen model—updates will keep coming. Adopt a test-and-deploy mindset instead of waiting for “perfect.”
  • “Our hardware isn’t ready.”
    Start identifying devices that need replacing now. You’ve got time, but don’t leave it too late.
  • “We can’t afford downtime.”
    Use Intune’s zero-touch deployment capabilities and tools like Windows Autopilot to minimize disruption.

Why Procrastination Is a Bad Idea

October 2025 might seem far away, but large-scale migrations take time. If you wait until 2025 to start planning, you’ll be scrambling to meet the deadline. Here’s why early action is critical:

  • Avoid the rush: As the deadline approaches, vendors and support teams will be swamped.
  • Stay secure: Upgrading sooner means fewer months spent on an unsupported OS.
  • Get ahead of the curve: Windows 11’s modern tools and features can drive productivity gains right now.

 

Final Thoughts

The end of Windows 10 isn’t just a deadline—it’s an opportunity. Moving to Windows 11 brings better security, improved productivity, and a platform built for the future of work. With tools like Intune and Windows Autopilot, the upgrade process can be streamlined and efficient.

So, don’t wait. Start planning your move today, and by the time October 2025 rolls around, you’ll already be reaping the benefits of Windows 11.

 

Ready to Get Started?
Let me know how I can help you make your Windows 11 upgrade seamless and stress-free!