So, Windows 10 is officially reaching end of support on October 14, 2025. No more security patches, no more bug fixes, no more support calls to Microsoft. Just you, your machine, and whatever’s left of your patching strategy.
I’ve still got a few machines running Windows 10—some tucked away in lab environments, others powering legacy tools that don’t play nice with newer builds. I didn’t rush to upgrade when Windows 11 dropped. Honestly, I wasn’t in the mood to deal with TPM errors and driver drama mid-project.
But now? It’s time.
Why I Held Off (And Why I’m Moving Now)
I held off because most of my gear “just worked.” But with EOL here, I can’t justify the risk anymore. I’ve seen what happens when endpoints go unpatched—ransomware doesn’t care if your machine is sentimental.
Started by auditing my fleet. Anything with TPM 2.0 and Secure Boot got bumped to Windows 11. The rest? I had to make some calls.
What I’ve Done So Far
- Upgraded my daily driver (ThinkPad X1 Carbon Gen 9, 32GB RAM) to Windows 11 Pro. No major hiccups, though I had to dig into BIOS to enable TPM.
- Subscribed to ESU for two legacy VMs running accounting software from the Stone Age. $61/year per device isn’t cheap, but rewriting that stack would be worse.
- Tested ChromeOS Flex on an old Dell Latitude. First boot was a black screen—turns out I missed a firmware toggle. Once sorted, it ran surprisingly smooth.
Stuff That Didn’t Go As Planned
- One of my desktops had TPM 2.0, but it was disabled by default. Took me longer than I’d like to admit to figure that out.
- My old HP LaserJet threw a fit post-upgrade. Ended up using a generic driver just to get it printing again.
- A few internal tools needed compatibility tweaks—nothing major, but enough to eat up a weekend.
What “End of Life” Actually Means
Let’s clear this up: your Windows 10 machine won’t suddenly stop working. It’ll boot, run apps, and connect to the internet. But without security patches, it’s like leaving your front door unlocked in a sketchy neighborhood.
Here’s what’s changing:
| Feature | Status After EOL |
|---|---|
| OS functionality | Continues to work |
| Security updates | Discontinued (unless you pay for ESU) |
| Microsoft 365 support | Ends August 2026 (security updates until Oct 2028) |
| Microsoft Defender updates | Continue until October 2028 |
| Technical support | No longer available |
Your Options (If You Haven’t Moved Yet)
- Upgrade to Windows 11
If your hardware supports TPM 2.0 and Secure Boot, this is the cleanest path. You’ll get Copilot AI features, better security, and a modern UI. Just be ready for a few UI quirks. - Buy into ESU
Works for legacy systems, but it’s a short-term fix. Starts at $61/year per device. Available for consumers too, not just enterprises. - Switch OS
Linux Mint, ChromeOS Flex, Zorin OS—these can breathe new life into old machines. But expect a learning curve and some app compatibility checks.
Final Thoughts
I’ve been through this before—XP, 7, now 10. Every time, it’s a bit of a scramble. But this one feels different. With AI features baked into Windows 11 and cloud-first tools becoming the norm, the gap between “supported” and “usable” is wider than ever.
If you haven’t started planning your move, now’s the time. Don’t wait until your antivirus stops updating or your compliance team starts asking questions.
