Windows 10’s Final Countdown — What I’m Doing Before October 2025
It’s official: Windows 10 support ends on October 14, 2025. If you’ve been in IT long enough, you know what that means—patches stop, bugs linger, and attackers start circling like vultures. I’ve lived through the XP and 7 sunsets, and trust me, you don’t want to be caught flat-footed again.
Why I’m Writing This
I’ve got a mix of machines in my environment—some running Windows 10 Pro on older ThinkPads, others on newer desktops with TPM 2.0. I started prepping for this transition earlier this year, mostly because I didn’t want to repeat the chaos of 2020 when we had to rush upgrades during lockdown.
What Actually Ends
After October 2025:
- No more security updates or bug fixes.
- Microsoft 365 apps stop updating on Windows 10.
- Defender Antivirus updates continue till 2028, but that’s just one layer of protection.
I’ve seen endpoints get compromised simply because someone assumed Defender was “enough.” It’s not.
My Migration Game Plan
Audit First, Panic Later
I ran a compatibility check using Microsoft’s PC Health Check and a few PowerShell scripts. About 40% of our machines passed the Windows 11 requirements. The rest? Either missing TPM or stuck on unsupported CPUs.
ESU as a Safety Net
For those older machines, I’m enrolling in Extended Security Updates (ESU). It’s not ideal, but it buys me time. Microsoft’s pricing is fair—$61/year/device for businesses. I’m using Microsoft Rewards to offset costs for personal devices.
Exploring Alternatives
Some of our kiosk setups are getting reimaged with ChromeOS Flex. Lightweight, secure, and perfect for single-purpose machines. I also spun up a few Azure Virtual Desktop instances for legacy apps that refuse to die.
Testing Windows 11 (Without the Hype)
I’ve been running Windows 11 on a dev box since April. It’s snappy, sure, but the UI changes threw me off at first. I haven’t touched Copilot+ PCs yet—still waiting for broader rollout and real-world feedback.
Lessons Learned (The Hard Way)
- Don’t assume ESU means full protection. It’s a stopgap.
- Microsoft 365 apps quietly stop updating—no warning banners, just silent decay.
- Compatibility issues sneak up on you. One of our finance apps refused to launch post-upgrade due to a .NET version mismatch.
Final Thoughts
This isn’t just another upgrade—it’s a strategic shift. Whether you’re a solo admin or managing hundreds of endpoints, start now. Audit your gear, test your apps, and plan your rollout.
What’s your migration strategy looking like? Are you going full Windows 11, sticking with ESU, or trying something else entirely? Let’s swap notes.
