If you don’t think SaaS jeopardizes every bit of your work, think again.

A cautionary tale.

Last Wednesday night, I got a horrible feeling in the pit of my stomach. I turn off my laptop every night, because of the security risk posed by a former boss. I keep everything but programs on an external hard drive, and I turn everything off. Not restart. Off.

And last Wednesday, there was one of those forced Microsoft updates upon shutting down. What made me worry: The screen said it would take around ten minutes. Which usually means disaster. Because the bigger the update, the more bugs. They seem to put everything in a garbage can and dump it into cyberspace, hoping they fix something.

Thursday morning, my fears were justified. Except silly me figured Microsoft would be on top of it.

First problem: No access to business email. Not on laptop. Not on iPad. Not Center for White Rose Studies. Not Exclamation! Publishers. I decided to work a bit on administrative tasks, reconciling bank accounts.

With another hmmm. Because of last year’s Intuit disaster, I’m keeping my books in Excel. Both companies have simple structures, so Excel is all I need. Except a great deal of data was missing. Keep in mind that Word and Excel are now SaaS, not perpetual licenses.

But I had proper licenses, not just for Microsoft 365 aka M365, which used to be Office 365. But also for email (an “exchange” for each).

Overnight, Microsoft had disabled the licenses. M365 and the exchanges. Gone.

It took two days to get that ticket resolved. Remote access from someone in India or wherever. I showed her the paid $0 invoice for M365, for nonprofit use. She said, “In May 2025, MS stopped those free licenses for nonprofits. So you have to renew.”

Note: My license cycle is November to November. In October 2025, Microsoft notified me that Center for White Rose Studies still qualified for $0 license for M365. I just had to pay 3x the former amount for the exchanges. Which I’ve been doing.

November 2025 through June 2026, no problem. Until Microsoft disabled my licenses. No prior notification. Just disabled.

I did as the techie required and clicked on “renew license.” She said I wouldn’t be able to see the dollar amount until I’d done so. Did it, and it “renewed” at zero dollars. Her response, “Hmm. I don’t understand.”

Also, this whole time, I was having to communicate via my iPad, because, well, can you say disabled licenses?

Sunday I turned on my computer—she had said to give it 48 hours to repropagate. Email worked. Excel worked. Word worked. But second monitor didn’t work.

Second monitor not working after an update is a known Microsoft issue. If you Google it, it goes back at least to 2020. They send out an update, the tech support site is flooded with second monitor issues, Microsoft fixes the bug. Next update it’s rinse and repeat.

Only last week’s update included TWO HUNDRED AND SIX (206) fixes. So they’ve not rolled out the fixes to the buggy fixes.

I’ve therefore spent the last two days with Windows tech support—although I’m “our” (read, my own) Microsoft admin, Windows issues cannot be reported through the Microsoft admin portal. Make it make sense.

Today I sat and watched while someone (likely an AI bot) did an advanced Windows 11 reinstall. He/It said that either this update or cumulative updates had corrupted system files in W11, necessitating the reinstall.

And of course, after all those hours, it didn’t work.

I won’t bore you with the following two hours of dealing with other people or bots (the chat itself identified “person named Rohan” as a bot). Except to say that it was more of the same. Unplug your monitor. Check your HDMI cable. Windows-P. Etc. Things I had already done a million times and had documented in both tickets.

After he/it recommended an advanced reinstall of W11, I nearly screamed. Not only did he/it recommend that, when I said, READ THE CASE FILE, he/it doubled down. Next suggestion was uninstall that update. But it’s deemed a security update and cannot be uninstalled.

The chat ended with, “You must simply wait for Microsoft to roll out the bug fix.”

So now I am facing a conundrum.

No way in hell I’m replacing this laptop with another Windows-based laptop. Next laptop needs to be a MacBook of some sort, but not the Neo. It’s great, but too limited.

But it’s out of my price range. Not just the hardware, but the WordPerfect and Proton perpetual licenses. And tech support to get it set up. And then today an email from last week’s techie, that Microsoft could disable these licenses whenever they choose? How is that even legal?

I wrote this on my iPad. Which is hard, because no keyboard or mouse. My alternative is a laptop with a small screen I can barely see. Microsoft’s bug—its known issue!—is harming my ability to do business. To write. To communicate.

And they don’t give a damn because there are zero consequences. Techbros have protection. There’s no laws that keep them on the straight and narrow. If it’s bad now, it’s only going to get worse.

Maybe typewriters and fax machines aren’t such a bad idea.

Postscript: Last year I moved everything off SharePoint to DropBox with redundant backup to an external hard drive. Gut was already telling me not to trust Microsoft. Highly recommend not trusting Google or Microsoft. Choose something like Dropbox that allows you to opt out of AI and isn’t owned by Google, Microsoft, or Meta.

If Dropbox ever sells out, I’m shutting them down.

Questions? Comments? Speak your mind below. Before doing so, please log in using the email address that corresponds to your orders or newsletter subscription. Note: MARKDOWN is the app's label for formatting shortcuts.

If you enjoyed this post and would like to leave me a tip, I would be grateful! Buy Me A Coffee!

Return to Policies, Not Politics index. Return to AI subsection.

No part of this post may be reproduced in any form or by any electronic or mechanical means, including information storage and retrieval systems, without written permission from the copyright holder, except for the “fair use” of quotations that are properly cited and credited, including identification of the translator if applicable. No part of this post may be included in any Large Language Model without proper licensing from the copyright holder, Denise Elaine Heap.