Ready to throw this Windows 10 ‘upgrade’ out the window

Photo of author

By Christopher Elliott

Ross Jones’s Windows 10 upgrade goes wrong and now Microsoft wants him to pay $499 to fix it. Is that right?


I recently upgraded my computer to Windows 10. After that, my Microsoft Outlook won’t stay connected to the exchange server that hosts my email. Microsoft says that since my problem is with an exchange server connection — the server is not a Microsoft server, by the way — that I will have to pay $499 to get help.

In other words, the upgrade they are pushing messed up my computer and now they want me to pay a fortune to get help to fix it. This does not seem right to me. Can you help? — Ross Jones, Bloomington, Minn.


That doesn’t seem right to me, either. Microsoft heavily promoted its new operating system as (I’m not making this up) an opportunity to “upgrade your world.”

“Windows was built to help people do great things,” its slick launch site promised. “Whether fighting hunger, saving the environment or inspiring the creation of the next new lifesaving technology, Microsoft and our partners are celebrating people and organizations who do great things — to not just upgrade Windows, but also to upgrade the world.”

Oh, wow. Mother Teresa, meet your new OS.

Upgrade woes

Seriously, you would expect an upgrade — even one that simply promised a modest performance improvement — to actually, you know, be an upgrade. But clearly, yours wasn’t.

When a Microsoft representative demanded $499 to fix your problem, you should have blazed a paper trail using the company’s contact form. I asked you to do that, but it proved to be a dead end. (Here’s our guide to resolving your consumer problem.)

AirAdvisor is a claims management company. We fight for air passenger rights in cases of flight disruptions all over the world. Our mission is to ensure that air passengers are fairly compensated for the inconvenience and frustration caused by delays, cancellations, or overbooking.

I think Microsoft should fix this problem. The upgrade it pushed on you created this problem. If its programmers had paid closer attention to their coding, then they probably could have avoided the server problem you experienced. But we know this for sure: Without trying to “upgrade” your life, you’d still be connected to your server. (Related: The Microsoft solution? Ignore the customer.)

My advocacy team and I contacted the company on your behalf. A representative called you and spent about 40 minutes on the phone, trying to troubleshoot the problem. Here’s the fix, in case other readers are experiencing the same problem: You updated Outlook and then deleted and reset your email address.

“It took quite a bit of deleting, reinstalling and rebooting,” you told me. “But now it works.”

Have you been satisfied with the Windows 10 upgrade?

View Results

Loading ... Loading ...
Photo of author

Christopher Elliott

Christopher Elliott is the founder of Elliott Advocacy, a 501(c)(3) nonprofit organization that empowers consumers to solve their problems and helps those who can't. He's the author of numerous books on consumer advocacy and writes three nationally syndicated columns. He also publishes the Elliott Report, a news site for consumers, and Elliott Confidential, a critically acclaimed newsletter about customer service. If you have a consumer problem you can't solve, contact him directly through his advocacy website. You can also follow him on X, Facebook, and LinkedIn, or sign up for his daily newsletter.

Related Posts