1. unlike password protected content servers , cloud connections in CC should not reprompt - NB dropbox does not. would be extremely annoying if it did.
2. all the clouds I use also have android apps and you only have to login in once with those, then they remember
my calibre CS is not password protected- AFAIk it's LAN only & even if some outsider figured out how to connect to it there are no state secrets therein
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