WatchOS is demanding I enter my AppleID password. It often blocks me from using my watch. I’ve used the phone trick, where it will show the password prompt on my phone. However, the iPhone won’t allow 1Password or the paste function in this field.
My AppleID is 20+ character password that was generated by 1Password and includes every single type of character that I can imagine.
I’ve tried over 10 times to enter it. I always get an error, often a “server error” when I’m finished. When I’m really lucky, my phone requires I re-authorize my AppleID on my phone. (Thank goodness 1Password handles that).
How do people get their passwords entered successfuly on their watch?
My watch has never asked my my AppleID password to my memory (and like you I have a generated password so I’d remember having to add it)
That’s one of the benefits of it being an accessory to the phone, you don’t (or shouldn’t) have to put your password in as it shares it from your phone.
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Apparently your watch is better than mine. I think I went through this pain on setup 2 1/2yrs ago now.
It’s possible I did it on the original Apple Watch back in 2015 and have completely forgotten.
This sounds really stupid, but have you rebooted both?
I recently set up a bunch of family member watches and had to enter at least once.
Thankfully, the password was a complex but memorable (e.g. XKCD style) password so a bit easier to type on the tiny watch keyboard.
I’d also recommend rebooting everything just in case it clears up the errors.
My phone and watch keep asking for appleID password and it is SO annoying. I keep entering it, accepts it. Weeks go by and then again. :-\
I’ve been getting this as well, maybe three times over the last six months. A couple years ago, I had this happen repeatedly, more like what Mark is experiencing, and a re-pairing fixed it. I never found a way to paste in the password either so I revealed it on a Mac and entered it with the iPhone keyboard.