Windows 10, problems with Disk Cleanup: what happens

Some users report a new problem with the latest Windows 10 update: this time it affects the Disk Cleanup utility

It's a decidedly unfortunate update the Windows 10 May Update 2020: another problem has popped up, this time with the Disk Cleanup utility. The problem (but for paradoxical reasons) fortunately affects very few users and Microsoft has already put a patch, albeit in a very strange way.

Practically, the problem consists in the fact that some computers can no longer boot up if Disk Cleanup is started right after installing the update to Windows 10 version 19041.21. This is a preliminary version of the May Update, reserved for beta testers enrolled in Microsoft's Insider program, released with the code KB4535550 in January 2020. Those who are not subscribed to this program, therefore, did not install this version or many of the new features it contains because (and here is the paradoxical thing) the May Update is causing so many problems that Microsoft still has not made it available via Windows Update to most users.

Disk Cleanup problems: how Microsoft solved it

The solution found by Microsoft for this problem is at least original: the Troubleshooter tool. Basically, the tool temporarily disables the automatic execution of Disk Cleanup, so that the computer can start and a new beta version of Windows, 19041.84, can be installed. Then Troubleshooter activates again, to check that everything is in order and, if it is, reactivates Disk Cleanup. This maneuver is completely automatic and cannot be started manually by the user, who can only check that everything has happened, by going to Settings> Update & Security> Troubleshooting> View Troubleshooting History.

Who is affected by this problem

As we said, this problem affects a very small number of PCs: the current version of May Update 2020 that you can download manually, in fact, is already quite a bit later than the offending version. However, due to the numerous problems caused by the first major six-monthly Windows 10 Update 2020, Microsoft itself recommends disabling the option in Disk Cleanup to automatically remove (10 days after installing an update) old files from the previous version of the operating system. You never know should a new problem pop up out of nowhere.