Symptom:
ICQ fails to connect. Status keeps saying "Connecting", after a while it transitions into "Error: Socket is not connected".
Diagnosis:
According to the debug window, Adium is trying to connect to the correct IP:
21:04:43: (Libpurple: dnsquery) IP resolved for login.oscar.aol.com
21:04:43: (Libpurple: proxy) Attempting connection to 64.12.200.89
21:04:43: (Libpurple: proxy) Connecting to login.oscar.aol.com:5190 with no proxy
21:04:43: (Libpurple: proxy) Connection in progress
However, running tcpdump on local machine shows something drastically different:
$ sudo tcpdump -i en1 host polaris
21:09:07.103354 IP polaris.house.net.60773 > polaris.house.net.aol: S 488964827:488964827(0) win 65535 <mss 1460,sackOK,eol>
Running tcpdump on the router also shows packets being sent from the Mac (polaris) to its own external IP (192.168.48.13) over the wlan interface (which makes no sense, why doesnt it loop back?).
Apparently, for some reason unknown to me, when AdiumX is trying to connect to the ICQ login server login.oscar.aol.com, in reality it tryes to connect from a high port to its own external IP.
The Mac in question is not having any connection problems in any other program, and the other modules of Adium being used (MSN and XMPP) are also working properly.