I've never seen anything like it.

A brouhaha has erupted with users who are incredibly frustrated over a Windows 10 upgrade problem. It seems Microsoft has been alerting users through the Windows Update program, which shows pop-ups as you work within an older operating system like Windows 8, that they should upgrade...or else. 

The prompts have caused a stir because they are annoying, intrusive, and aggressive. Yet, they also point to a larger problem, one that likely won't go away anytime soon.

First, some background. As you know, I was one of the big champions for Windows 10 when it first started shipping. I hated the interface in Windows 8 and once called it an epic fail, but Windows 10 brought back the familiar Start button (which is now more of a menu). I've watched people who are not that computer savvy figure out how to find basic settings, use the search box, and find apps much easier than ever before. In Windows 8, my biggest reason for disliking the OS so much was due to how people who get so confused by the tile interface, which is now less prominent.

Windows 10 came out last year around this time. You have until July 29 this year to get the free upgrade if you are using any computer running Windows 7 or Windows 8. Now, that cost is "free" in terms of dollars but not necessarily in time or any related support costs. Some users have told me directly that they spent a day trying to install the upgrade after agreeing to the prompts. Others have said they declined the update, but Windows Update proceeded with the update anyway.

Why is it so important to Microsoft that legacy users upgrade? What's causing people to get so frustrated and annoyed that they email me out of the blue?

Ironically, part of the reason has to do with a legitimate security concern, because those older operating system do not have the latest security features such as Microsoft Hello (which uses a fingerprint reader, face scanning, or a PIN code to authenticate your login) or full-disk encryption. It's an irony because users are reporting that they have turned off Windows Update to avoid the constant nagging, which means they are also not receiving the latest security updates.

Of course, Microsoft also wants everyone on the new OS for many other reasons. One is that their overall support costs will be lower if everyone is on the same OS. There are some features, particularly in some of the built-in gaming apps, that generate revenue for Microsoft through ad placements. And, it's just better for any tech company when people upgrade. It means you are more likely to use the Windows Store and purchase apps, movies, and games. It means you are more likely to stick with a new, fresh, and clean OS.

What's most interesting to me is how many users are worked up over this issue. It's astounding. I've received dozens and dozens of messages from people in the past few days complaining about the upgrade reminders. Here's my theory about why this is a problem. The concept of "enabling technology" means the tech blends into the background. In the Google Chrome browser, it means every site you visit just works, loads quickly, and the browser updates itself in the background. In a newer car like an Audi A4, it means you connect your iPhone and your main apps for music, navigation, and texting show up on a touchscreen using Apple CarPlay.

Enabling technology means we are enabled, but the Windows Update problem makes it seem like the technology is taking over. It's disabling tech. It's also intrusive to people who need to focus on their work. The user base is telling Microsoft: "We will upgrade when we are good and ready, now please go away."

The frustration is also due to the incessant nagging. I've experienced this myself with anti-virus apps that nag me constantly to upgrade or install some extra feature or make an update. It doesn't seem like enabling technology, it seems like a come-on or a way to generate revenue. The entire problem with Windows Update seems like yet another example of a major tech company having too much swagger. We mostly want to be left alone to work and make our own decisions.