Don't know whether anyone here has been plagued by repeated requests for the Apple ID password which get into a confusing spiral of repeats? Anyway, just in case, here is a good summary of the situation and an explanation I found today. Can now use iMessage without the pain..
From Apple support pages:
"But it is not obvious whether this is what I was meant to do. The Apple help page on app-specific passwords is rather unhelpful - it doesn't even mention which of Apple's own apps require app-specific passwords (such as iMessage and FaceTime), let alone clarify whether you can/should use the same password for those apps on different devices, or how you're meant to respond to random mystery iCloud login prompts that pop-up from time-to-time (generate a new app-specific password? Re-use the existing one? Not at all clear.)
The actual enrolment process works by demanding your Apple ID password, then chastising you for entering the wrong password, followed by prompting you to visit appleid.apple.com/ and generate an app-specific password "for iMessage and FaceTime". But the subsequent random mystery iCloud login prompts make no mention of iMessage or FaceTime, which is why it's difficult to know how to respond.
Allegedly a similar process is meant to happen on iOS - but the iOS dialog pictured in this arstechnica article never appeared for me on iOS; I just got various Apple ID password prompts which rejected my Apple ID password, but appeared to accept the app-specific password that I'd previously generated on OS X. ("Appeared to accept" of course means the dialog disappears, they don't actually say anything helpful).
A further annoyance is that when any kind of iCloud password prompt appears on iOS, the prompt is modal, which makes it impossible to paste in the app-specific password that I'd saved into my password manager app (1Password). So I had to cancel that dialog and force a re-login to iMessage and FaceTime by turning them off and on again, just so I could paste the password in. But this had the side-effect of disabling Text Message Forwarding, so I had to re-enrol that service.
As I said, I got it all working in the end by simply generating one app-specific password and using it in all 5 scenarios above - but it took a lot of trial-and-error to get there and it wasn't straightforward at all.
God knows how someone who is not IT literate can make any sense of this."
I still had trouble getting the other devices on iOS to co-operate but cracked it by manual copying and inputting the keychain password.
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