Many "Cancel" dialogs are worded poorly. Recently I was ordering some sneakers online when I suddenly wondered whether I had specified the right shipping address. To double-check, I clicked on the browser's back button. A warning appeared: If I went back now, this would cancel my order. Below, there were two options: Continue or cancel. I stared at my choices, dumbfounded. If I pressed cancel, would this cancel my order or would it cancel the "back" command? And what if I continued? Just to be on the safe side, I closed the browser tab entirely and got my shoes elsewhere.

A dear aunt of mine hits "Cancel" on anything that offers her the choice. At some point, someone (possibly even me) told her that if she wasn't sure about a dialog, pressing cancel was always the safest option. She followed that advice way too closely.

The perils of cancelling well-meaning dialogs

One day she begged me for help because her "anti-virus wouldn't update anymore." I sat down at her computer and found it to be running a three-year old version of the anti-virus product. Its status confirmed that it had stopped updating its signatures a week ago. The reason was simple: The manufacturer had stopped supporting the old version of its product.

A series of cautious questions to my aunt revealed that the anti-virus had been offering her to update itself for more than a year now. This, of course, would have been free of charge, since her license ran for another three months. But since the updater never made this clear, she had always cancelled the dialog and was proud to have managed the "crisis" by herself. Only when the anti-virus vendor shut down its update service did she finally cave in and ask for my help.

I tried to explain that the well-meant advice on handling unexpected dialogs did not mean to always blindly press "Cancel," but I doubt this really reached her. At least we were able to reach a new agreement: If a dialog pops up and she doesn't know what to do, she will take a photo before cancelling. That is – if there is still a Cancel button to be pressed.

Windows Update: No way out

Of course, software developers by now have realized the perils of users trying to cancel out of everything. The most prominent example is Windows Update: Windows XP users were masters in ignoring the operating system's prompts to restart their machine to complete pending updates. If Windows Update was trying to install a patch for a critical security flaw, stubbornly canceling all restart requests could have disastrous consequences such as malware infection, data loss or both.

This situation led the designers of Windows 7 to decide that system security was more important than users' data. If users didn't reboot when Windows told them to, it would take matters in its own hands. For the Greater Good, of course.

If Windows felt the urgent need to process an update, it would issue a couple of warning messages, but "Cancel" was no longer an option. Eventually Windows would no longer allow further postponements. Instead, it shut down, installed its updates and rebooted, even if applications were open with unsaved files.

Users rebelled in their own way, by installing tools such as "Shutdown Guard" or disabling Windows Update while working on important projects. Windows 10 went one step further: Initial versions were prone to shut down without advance warning and install its update – damn the torpedoes, full speed ahead.

Well-meant, yet ill-conceived

I didn't think the problem was so bad until Windows Update suddenly shut down my computer and spent half an hour installing one of its ignominious "feature updates" – even though I had been furiously typing away at an article. This happened more than a year ago and my blood still boils when I recall the moment: About half an hour of work, gone in an instant – just because Windows couldn't be bothered to give me one last chance to save my files before it shut down.

Naturally, the same thing happened to my aunt in the middle of her tax returns. It was anything but a confidence-building moment: She is now firmly convinced that her computer is out to get her. And she's far from being an isolated victim: The web is full of articles on how to prevent Windows Update from rebooting of its own volition. Some approaches involve disabling the UpdateOrchestrator task in the Task Scheduler, others involve software to constantly shift the "active hours" window. Some extremists even recommend to completely deactivate the update service (yikes!).

The reason I'm not going into more detail about these approaches is that Windows Update has become a moving target. Methods which work in one version of Windows 10 will fail to work after the next Feature Update. Also, Microsoft is actively working to improve the way Windows Update detects whether the computer is currently being used. In any case, it's a very bad idea to disable Windows Update altogether.

One thing is for sure, however: Don't expect Microsoft to restore a "Cancel" button. I have a feeling that they know exactly what my aunt would do.

Do you have your own "Abort, Retry, Ignore" experience? Let us know in the comments.