Or maybe it's always had problems based on my Google results.
One of my PCs was disconnected from the internet for maybe a month. Last night I discovered 23 "important" updates that needed to be downloaded and installed.
What a PITA! There were several ways it failed: e.g. hanging on "Creating a restore point" or hanging on "Configuring Windows, do not shutdown or turn power off."
All of the failure modes were seen by numerous others, judging by the questions asked on the internet and which resulted in the usual mixture of useless and sometimes helpful advice.
What worked for me was to go to Action Center -> Troubleshoot Common Computer Problems -> System and Security -> Fix Problems with Windows Update.
I had to do this twice over the course of about 2 hours after fiddling around unsuccessfully in Safe Mode, restoring check points, which solved nothing. I ignored the arcane and potentially dangerous registry-related advice, virus removal "this *is* the problem" type advice and sundry Microsoft MVP directives to do X to solve the problems, but it resulted in a lot of wasted time just to evaluate the advice.
The "Fix Problems with Windows Update" would say something like "checking for problems", "finding additional problems" and then would end with a little green box with a check labeled "fixed". No details were given.
Nothing like this ever happens when I update my Mac.