I had to call Apple yesterday as I didn't know the answers to my security questions to login to one of their websites.
Been there, I feel your pain.
Similarly: I lost my iPhone a few days ago (as in, I knew it was somewhere in the house/garden/car, but couldn't figure out where I'd left it). No problem - I have the Find my iPhone service set up.
So on my Mac, I went to the icloud.com Find-my-device page, to be greeted with
YOU HAVE A WEAK PASSWORD. YOU MUST CHANGE YOUR PASSWORD NOW. RIGHT NAO!!1!. IMMEDIATELY!!
Yeah, great, perfect timing Apple... when someone has lost their phone and is mildly freaking out, is EXACTLY when you should insist on changing their password to suit you (note: I don't keep anything sensitive on my iCloud account because I hate all things cloud, so a "strong password" is for Apple's convenience, not mine).
Why not something like "Your password doesn't meet our latest requirements. Please change it at your earliest convenience"???
So, anyway, muttering and grumbling, I changed the password. As most people in this situation do, I just capitalized the first letter and added a symbol and a number on the end e.g "Sesame^1"... that'll teach them...
Then got hit with a blizzard of system prompts on the mac.
ICLOUD needs your new passsord NOW!!
MAIL needs your new password NOW!!
ITUNES needs your new password NOW!!
..one after the other, appearing as fast as I could deal with them.
Once I found the phone, I got similar modal, non-skippable prompts. "Your password needs to be updated - go to settings NOW".
What. A. Shitty. User. Experience.
Seriously, Apple, WTF?
What has happened to all the tech companies, that they now think THEIR requirements and way of doing something trumps anything up to and including user convenience?