He's Ready to Throw His Windows 10 Upgrade Out The Window

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

Question: 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.

Answer: 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.

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.

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.

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."

Christopher Elliott specializes in solving intractable consumer problems. Contact him with your questions on his advocacy website. You can also follow him on Twitter, Facebook and Google or sign up for his newsletter. (Illustration by Aren Elliott.)