Re: how to keep iCloud sign in from popping up all the time. Apple started requiring application specific passwords/keys for iCloud access for apps that use iCloud data when 2 factor authentication is active.I first encountered this issue with Fantastical.e: how to keep iCloud sign in from popping up all the time. Apple started requiring application specific passwords/keys for iCloud access for apps that use iCloud data when 2 factor authentication is active.