Pidgin 2.7.3 on Debian has an issue where the configured accounts do not connect right away on startup. This issue is related to the network manager configuration inside pidgin itself. Fortunately, the issue can be simply resolved by starting pidgin with the -f flag. This forces pidgin to ignore the network manager’s status and attempt to connect no matter what. If you are having problems with having to re-enable each account in pidgin after you start the application, then add the -f flag to the startup command you use, and your problems will hopefully be solved.