Lesley Carhart 
One of my favorite modern cybersecurity design things is when something on the server side authentication fails instead of your actual credentials / MFA, but the failure error message is identical so you spend an hour doing resets and second guessing yourself only to have everything work perfectly a little later on.
Tim Panton@hacks4pancakes There is a _fantasticly_ annoying feature in Apple Music - where if you need to sign in on a rebuilt machine that isn't synced to iCloud 3 or 4 different service all popup the same login dialog in turn. I initially assumed I'd mistyped the credentials - but no. Super confusing to anyone who encounters it.