We have yet another issue, this time 3rd party software clashing with Microsoft’s Remote Desktop.
Sometimes (and I don’t know why) the Skype installation enables as default the use of alternative ports – 80 and 443 to be precise. Now those ports are widely and commonly used by more than just Skype (take your localhost for instance, 443 is used for secure (https) connections). And we came across a scenario where Skype’s default settings wouldn’t enable stable connection to any remote machine runnig Windows.
The spoiler: to fix this go to: Tools > Options > Advanced > Connection > and uncheck “Use port 80 and 443 as alternatives for incoming connections” as of v3.6.0.248.
BTW – did you know Windows Skype doesn’t really work on Windows 2008 at all?
Update: Skype has released v3.8 several times now and even the Beta 4.0 seems to be working just fine on Windows 2008. Solved.