Jim Rossman: Older versions of Windows will cause issues – eventually

This week a reader writes with a problem, and tells me how he solved it, but he has a larger question about the cause:

"I have been using Hotmail for over 30 years without any issues. A couple of weeks ago I kept facing a situation when Hotmail would keep asking me to change my password. It directed me to a backup email (Gmail) to get a code. When I entered the code, it would loop me back to get another code. This kept repeating. I was using a desktop with Windows 10. Suggestions I received from the web was to clear my cache and/or use another browser. Nothing worked. I finally deleted the apps from all my devices, re-installed them and now I have access. Could it be that using Windows 10 and suspension of support by Microsoft could be corrupting the system? Is Microsoft forcing the issue of transitioning to 11 and Outlook?"

The short answer is yes…and no. This is all just my opinion, not anything official.

OK. The real answer is that Microsoft has ended support for Windows 10, so those systems are not really given much (if any) consideration when new security features are rolled out.

Microsoft is constantly updating its mail security to try to keep one step ahead of the hackers. If you're using an unsupported version of the operating system and an unsupported browser or an older version of a mail app to check your mail, it may all work great…until it doesn't.

You won't get any warning. No window will pop up to advise you to update to Windows 11 or to the newest version of the Edge browser or the Outlook mail app. Things will just stop working.

For a while, you may be able to work around it by uninstalling and reinstalling or using a different browser, but eventually, you're going to run into a problem that you can't work around. This will likely be because of a change in something at Microsoft's end that your older hardware and software isn't equipped to handle.

The online community is a great place to ask questions. There are Microsoft message boards and subreddits where you can toss out your questions and ask for assistance. You'll find some helpful people who will try to get you back up and running, but eventually you'll run into a problem that will stump you, and that's when you'll need to update. Start saving your money.

Here's a tip. If you are having problems on the computer, try using your phone. Chances are your phone has a more recent operating system and the problems facing your aging PC will likely not be an issue on your phone.

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This story was originally published June 10, 2026 at 4:29 AM.