Windows 10 is nearing its second and much less forgiving expiration date. Microsoft cut off standard support back in October 2025, but the Extended Security Updates program many businesses leaned on as a bridge only buys so much time, and year one of that bridge ends October 13, 2026. After that, any device still running Windows 10 without a paid ESU subscription stops receiving security patches altogether. Full stop.
More Machines Are Still on Windows 10 Than You’d Think
If your organization has been putting off the Windows 11 migration, you have company. As of this August, Windows 10 still held roughly 45.5 percent of the Windows market, according to Statcounter, even with the free support window already closed for most users. A lot of businesses treated ESU as a long term fix rather than what it actually is, a short runway to finish a migration that should already be underway.
That matters because the math on what happens next isn’t close. Verizon’s latest breach data shows vulnerability exploitation grew 34 percent year over year as an initial access method, and SonicWall’s 2026 research names unpatched systems as one of the top drivers of SMB breaches for the third year running. Once Windows 10 stops getting patched, every newly discovered flaw in it stays open, permanently, on any machine still running it. For businesses tracking toward CMMC, NIST 800-171, HIPAA, or PCI-DSS readiness, an unsupported operating system is also one of the fastest ways to fail a control review before an assessor even gets to the harder questions.
What “Ready” Actually Looks Like
For an SMB, getting ahead of this deadline is less about panic and more about sequencing. A few things worth doing now, before October:
- Inventory every endpoint and flag which ones are still on Windows 10, then check hardware compatibility against Windows 11’s requirements, TPM 2.0 trips up more machines than people expect.
- Budget for the gap. ESU pricing for businesses starts around 61 dollars per device in year one and roughly doubles each year after, and it’s cumulative, so waiting doesn’t save money, it costs more.
- Prioritize by exposure: machines handling client data, finance, or remote access should move first, general workstations can follow behind.
None of this needs to be a scramble in September. The businesses that come out of this cleanly are the ones treating it as a planning exercise now rather than a fire drill in six weeks, and that planning is a lot cheaper than the alternative.
Where This Fits Into a Bigger Picture
Windows 10’s exit is really just one line item inside a much larger discipline: keeping every endpoint, server, and piece of infrastructure current without anyone having to think about it. That’s the heart of the operational management work a managed IT partner should be doing quietly in the background, patching, monitoring, and flagging aging hardware before it becomes a liability. For businesses that haven’t mapped out a device replacement and upgrade timeline, this deadline is also a good forcing function to build one as part of a broader IT roadmap tied to budget cycles rather than emergency spend.
Cloud9 Tech Solutions has spent years helping Massachusetts businesses operate like enterprise organizations without the enterprise complexity, and unglamorous deadlines like this one are exactly where that discipline pays off. The businesses that ask what’s next instead of what’s broken are the ones who aren’t scrambling come mid October.
Don’t Wait for the Deadline to Find You
If you don’t have a clear answer right now for how many Windows 10 devices are still active on your network, that’s worth fixing this week, not in October. Cloud9 can help you inventory your environment, map out a realistic migration timeline, and make sure nothing slips through the cracks with an unpatched machine still sitting on your network past the deadline. It’s a small project now. It’s a much bigger one after October 13.
Schedule a free security assessment with Cloud9 and get a clear picture of where your business stands before the deadline arrives.