Recently I wrote about the cost of not changing, and legacy Windows machines were part of that conversation. Today’s note is a follow-up, because something has come up in the conversations since that’s worth naming on its own.
Windows 10 support ended on October 14, 2025. That was seven months ago. In the run-up to that date, Microsoft announced an extension program that would let users keep receiving security updates for one additional year. The news got covered, the news got passed around, and the news got filed in a lot of people’s heads under “good, I have more time.”
Here is what I keep running into. The extension is real, but the extension is not something that happened to your computer. It is something you had to actively do. For businesses, it costs money. For consumers, it costs less money, but it still requires enrollment. If you did not enroll, you did not get the extension. You got the headline.
And even if you did enroll, the extension is a runway. It ends on October 13, 2026. That is roughly five months from now.
So there are really two versions of the same pattern going around. The first is the owner who heard “Windows 10 was extended” and used that as a reason to stop thinking about it, without ever enrolling. That machine has been unpatched since October. The second is the owner who actually enrolled, and is now treating a one-year bridge as a permanent solution. The clock on that one is running faster than it feels.
The word “extended” does something to the brain. It lowers the temperature on a piece of news that should have raised it. Microsoft’s own messaging moved a few times, and most business owners had bigger fires to fight last fall than the operating system on a machine that was still booting up every morning.
May is a better month to look at this than September. In September, every IT provider in the country will be having the same conversation with everyone who waited, and the migration calendar fills up fast.
If you are still on Windows 10, the question is not whether to upgrade. The question is which of three buckets you are in. Some machines can upgrade to Windows 11 in place, and that is a relatively short job. Some cannot, because the hardware does not meet the requirements, and those need to be replaced. And some are running a piece of business software that does not play nicely with Windows 11, and that is its own conversation that takes longer than the upgrade itself.
The cost of finding out which bucket you are in right now is small. The cost of finding out in October is not.
If you want a second set of eyes on what you have running, I am happy to help you figure out where you stand.
Until next time, keep IT simple.
Dave
