One Foot Through the Door…and One Foot Out… Microsoft Announces Flexible Transition Options

by | Jul 15, 2025 | SSMN Features

ACTSmart I.T.

The tech world is still adjusting to the changes coming down from Microsoft and their main operating system, Windows, as they are pushing for everyone to move on up to Windows 11. But… not everyone has flown the Windows 10 ‘coop’ quite yet. Thankfully, we have David Snell of ACT Smart I.T. in Wareham to guide us through this big change. 

On this week’s Tech Talk, which airs every Tuesday morning at 8:10 on The South Shore’s Morning News, David says this about Microsoft offering some transitional steps between Windows 10 and Windows 11:

As of July 2025, Windows 11 has finally overtaken Windows 10 in market share. According to StatCounter, Windows 11 now runs on 52% of all Windows PCs, while Windows 10 has dropped to 44.6%. That’s a dramatic shift from just a month earlier, when the two were nearly tied at around 48% each.

The surge in Windows 11 adoption is largely driven by Microsoft’s aggressive push and the looming end-of-support deadline for Windows 10.

Still, that leaves hundreds of millions of PCs—many of them still perfectly functional—running Windows 10. And that’s a problem for Microsoft. They’re essentially saying they won’t patch known security flaws in their own software unless users pay up. The patches exist—they’ll be sold to those who can afford them—but everyone else will be left increasingly vulnerable.

So, it wasn’t too surprising when Microsoft blinked. On Tuesday they announced a more flexible approach to Extended Security Updates (ESU) for individual users. Here are the three options:

  1. Use Windows Backup to sync your settings to the cloud — free.
  2. Redeem 1,000 Microsoft Rewards points — also free.
  3. Pay $30 USD for one year of ESU coverage.

Once you choose an option and follow the steps in the enrollment wizard, your PC will be covered from October 15, 2025, through October 13, 2026. The wizard is already available to Windows Insider Program members and will roll out to all Windows 10 users by mid-August

You can read David’s full blog about this by clicking here.  And listen to this week’s Tech Talk as Rob, Beth, and David discuss all these changes: 

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