When I updated my Air to 10.10.5 after the reboot I was asked to create an app-specific password for iMessage and Facetime because 2 factor authentication is enabled. I thought it was weird but created the password and everything worked fine. A couple of days later I updated other machines to 10.10.5 and I was not asked to create any passwords - for now. Not only that another couple of days later other macs running the same iCloud-account asked me to create app-specific passwords for iMessage & FT, even iPhone and iPad (running iOS 8.4.1) wanted me to create them app-specific passwords. I tried reinstalling 10.10.5 via combo update, I deleted and re-logged-into the iCloud accounts on both, OS X and iOS - nothing changed. Is there anyone else having problems with iCloud/iMessage/iSomething since the latest updates?