It seems like Azure DevOps migrated to some new login mechanism recently which is visibly slower than the old one, and I was seeing random failures prior to today.
I have also noticed strange behavior that was not present before this perceived update, e.g. basic auth challenges and pop-up windows if I'm waking up my computer and still have azdo pages open.
I believe that was a change to auth from a few weeks ago and is affecting every MS service. Not sure though and it does work, but it doesn't work gracefully.