Generate Specific Pass..... whats going on?

[DJTaurus]

Each time i reboot my Mac i get the message below

When i enter my pass it promts me to safari in order to generate a specific pass for imessage and facetime... i generate the pass but then i cannot login to view details on these both apps.... also each time i reboot i get the same message.

 

[DJTaurus]

Why it doesnt accept my password despite i am logged in icloud on my mac...? Same happens with imessage...

 

[Honza1]

Why it doesnt accept my password despite i am logged in icloud on my mac...? Same happens with imessage...

Just to make sure - if you generated application specific password for iMessage and Facetime, you are using that application specific password for them? I screwed this up few times - once application has app specific password, you cannot use your usual iCloud password for that application. You must use the app specific one. YOu can generate new one, if needed.
I suspect your iCloud applications cannot log in on reboot since the password they are trying to use is the main iCloud password and not app specific one.