I've also been experiencing the same behaviour for some time now,
exactly as Thelasko laid out in the description.  I, too, realize gufw
is just a gui & whether it's running or not shouldn't have an affect on
anything once ufw is enabled, but this is what appears to be happening.
On a fresh install of Xubuntu 8.10:

Installed pidgin, installed gufw
Ran gufw, checked 'Firewall enabled' box, closed gufw
Reboot system, connect to internet
"$ status ufw" reports 'Status: loaded'
Run pidgin -> accounts cannot connect (AIM, Yahoo, MSN, Jabber)
Run gufw -> now pidgin's accounts suddenly *can* connect..

Upon reboot, pidgin cannot connect again until I run gufw.  I have
however noticed that for whatever reason, if I don't run gufw, but wait
a while, pidgin will find itself able to connect after several minutes
(~15?).

Maybe this is just something silly & simple we're just overlooking?
It's frustrating, nonetheless. >_<

-- 
Pidgin can't login without gui-ufw running
https://bugs.launchpad.net/bugs/307590
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