Here’s How I Upgraded to Windows 11 for Free—Without Breaking My Setup

I’ve been dragging my feet on this for months. Windows 10 has been solid for me—predictable, stable, and I’ve got muscle memory baked into every corner of it. But with support ending on October 14, 2025, I figured it was time to stop dodging the inevitable.

This isn’t a guide. It’s a postmortem of how I actually upgraded three machines—each with its own quirks, BIOS tantrums, and “why is this even happening?” moments.

Why I Finally Bit the Bullet

I’ve got a mix of gear: a ThinkPad X1 Carbon (Gen 9), a Ryzen desktop I built in 2020, and an old Dell OptiPlex I use for testing weird network setups. All three were running Windows 10 Pro, patched up, and mostly behaving.

The tipping point? A client asked if upgrading would break their Hyper-V setup. I didn’t want to guess. So I ran the upgrade myself—no sandbox, no VM. Just raw installs on live machines.

Method 1: Windows Update (Worked… Eventually)

Started with the ThinkPad. TPM 2.0? Check. Secure Boot? Enabled. UEFI? Yep. I hit “Check for updates” and… nothing. No Windows 11 prompt.

Turns out I had paused updates weeks ago and forgot. Unpaused, rebooted, waited. Still nothing.

I ran the PC Health Check tool, which gave me the green light. Then, finally, the upgrade option appeared. The install screen just sat there—black, silent, almost mocking me—for a good 10 minutes before anything moved. But it worked. No data loss, no driver issues. Just a new OS and a centered taskbar I didn’t ask for.

Method 2: Installation Assistant (Cleaner, but Finicky)

On the Ryzen desktop, I used Microsoft’s Installation Assistant. It felt more direct, but halfway through, the installer froze. I checked logs—turns out my BIOS was two versions behind, and Secure Boot was off.

I flashed the BIOS (ASUS board, so not too painful), enabled Secure Boot, and tried again. This time, it flew through. Apps stayed intact, even my weird OBS setup survived.

Method 3: ISO File (For the Brave)

The OptiPlex was a mess. No TPM, Secure Boot disabled, and BIOS from 2017. I knew it wouldn’t pass the checks, so I used Rufus to create a bootable USB that bypassed the requirements.

It installed, but Windows Update refused to push cumulative patches. I had to manually download KB files and install them one by one. Not ideal. I wouldn’t do this on a production machine.

Lessons I Learned

• BIOS matters. Don’t assume it’s up to date just because the machine boots fine.
• Secure Boot is sneaky. Some boards say it’s enabled, but it’s not active until you set a platform key.
• Legacy antivirus tools can silently block the upgrade. I had to nuke one with Safe Mode.
• Rufus works, but unsupported installs are a gamble. You’re basically off the grid.

Final Thoughts

Upgrading to Windows 11 is free, but it’s not frictionless. If your gear’s compliant, use Windows Update. If not, weigh the risks. I’ve done it three ways now, and each taught me something new—mostly about how fragile “supported” can be.

Have you upgraded yet? Did your BIOS throw a tantrum? Did Windows Update ghost you for days? I’d love to hear how your setup handled the switch—especially if you’re running anything older than 8th Gen Intel.