I’ve been having the same issues with my site for the past week, trying to get the critical CSS to generate. Well, low and behold, if it didn’t just generate. So obviously it is not my site but something to do with the program itself given the number of people having issues.
Also wanted to comment that I noted it says to do this whenever we make changes to the html or css structure of our sites. I haven’t taken any of those steps/actions, so can’t see why it would have been necessary in the first place.
All is well – for now.