Thanks for the comment, please try to launch checkgmail from terminal with -v 
and see if it says something useful.
Is it also possible for you to try to remove nwmanager and see if the problem 
is still present? 

By the way in the canghe log of last version you can read: "BUGFIX: If
version 1.10 was started when no network connection was present,
checkgmail got caught in an infinite loop when trying to log in, with
predictably disasterous consequences ... :(  This has been fixed by
adding a 30 sec sleep period between trying to connect" see
https://sourceforge.net/project/shownotes.php?group_id=137480&release_id=459054

Thanks

-- 
Error:500 Cant connect to www.google.com: 443 (bad hostname)
https://launchpad.net/bugs/74141

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