Visual Studio stuck in 'Restart Required' after update

A while ago, my Visual Studio installation was caught in a “please-reboot-loop” after an update.

After letting auto-update Visual Studio 2019 to a newer version, it finished with a request for a reboot; well, I granted it, with teeth grinding…

The attempt after the reboot to start Visual Studio again (directly or via double-cliking a *.sln file) or running the VS installer failed: It still/again wanted a restart of the machine. Oh well, did it a second time, but that didn’t solve the issue either.

Then I began searching around on the internet, but could not find any helpful tip (either it was before the link at the top existed, or I simply did not find it back then). So, in the end, I completely uninstalled Visual Studio and set it up fresh again (luckily, I save my settings occasionally via Tools/Import and Export Settings…).

Fast forward: Some months later, after skipping a few updates out of fear of this (and because I didn’t really need them), I dared to do it again – and the same issue hit me again! *grrr…*

Fortunately, this time I found a page in the ‘Visual Studio Developer Community’ with the solution to the problem:

Looking at your situation, it is possible that the volatile key used for designating a needed reboot is somehow orphaned on your machine and leaving you in this state.

This is a rare event we have seen with how Windows handles volatile registry keys. Can you please check the following registry key to see if it is set? If so, removing this key should unblock you.

32Bit: HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\VisualStudio\Setup\Reboot

64Bit: HKEY_LOCAL_MACHINE\SOFTWARE\WOW6432Node\Microsoft\VisualStudio\Setup\Reboot

Reply by Matt Cavallari [MSFT] 2019-05-24