Why I Am Not Upgrading To Windows 11

In this post and video, I’ll explain why I’m not upgrading to Windows 11 on my main PC just yet—even though the free upgrade is available. The short version: my workflow is tuned for Windows 10, I rely on Dragon NaturallySpeaking, and Microsoft is still providing Extended Security Updates (ESU) for Windows 10 through October 2028, so there’s no rush.

Context: Windows 10 Security Updates

Initially, it looked like Windows 10 updates were ending soon, which understandably worried many of us. Microsoft has since extended security updates, meaning you can keep using Windows 10 safely for years if you participate in ESU. I show how to navigate the Windows Update pages and enroll for ESU in the related posts below.

My Setup

Daily driver desktop that’s eligible for Windows 11.
10+ year-old laptop that still runs perfectly on Windows 10.

There’s no reason to discard working hardware just because a new OS exists—especially when security updates continue.

The Key Reasons I’m Staying on Windows 10

1) Dragon NaturallySpeaking compatibility and cost

I use Dragon NaturallySpeaking (speech-to-text) as part of my daily workflow. Windows 11 can be finicky with older software versions. Upgrading Dragon to ensure perfect compatibility can run to the high hundreds of pounds, which feels unnecessary while everything functions smoothly on Windows 10.

2) Proven stability

Windows 10 is mature and predictable. It’s been refined for years and is rock-solid for my video creation, editing, and voice dictation work.

3) Software and device compatibility

My production stack—including recording gear, microphones, audio drivers, and editing tools—works flawlessly on Windows 10. Staying put avoids unexpected driver quirks or plugin issues.

4) Familiar, efficient interface

I’m fast in Windows 10. The muscle memory, right-click menus, and layout help me get work done without friction. Moving to Windows 11 would mean re-tuning lots of little habits.

5) Lower system overhead on older machines

Windows 10 tends to be less resource-hungry on older hardware. If your PC is modestly specced, that can translate to a snappier, quieter system—useful for editing and screen capture.

6) Extended Security Updates through 2028

With ESU in place, my Windows 10 machines can keep receiving critical security updates for years. That removes the urgency to jump to Windows 11 before I’m ready.

7) No reconfiguration needed

Upgrades often trigger a round of re-installs, driver updates, privacy tweaks, and settings changes. Staying with Windows 10 means I keep creating without downtime.

How I Enrolled for Extended Security Updates

From Settings → Windows Update, I see the Windows 11 offer, but I choose Enroll for Extended Security Updates for Windows 10 instead. After confirming the ESU prompt, my device shows it will receive extended security updates. If you want the click-by-click walkthrough, see the related guides below.

Who Should Stay on Windows 10?

Creators who rely on specific software (like Dragon) that may not be 100% happy on Windows 11 without paid upgrades.
Anyone with older—but perfectly good—hardware that runs better on Windows 10.
People who value a stable, familiar environment and don’t want to reconfigure their systems right now.

Who Might Consider Windows 11 Now?

Users buying new hardware designed for Windows 11.
People who want the latest UI features and are happy to re-tune their workflow.
Those whose apps and peripherals are confirmed to be fully compatible on Windows 11.

My Plan

I’ll keep using Windows 10 for at least the next year, monitor how my tools behave under Windows 11, and move when there’s a clear benefit—without sacrificing productivity or paying for upgrades I don’t need right now.

Have Your Say

If you’ve stayed on Windows 10—or upgraded to Windows 11—let me know how it’s going for you. What worked well, and what would you do differently next time? Your feedback helps others decide what’s right for their setup.