Firewall – Applying outbound connection rules PER USER in Windows Firewall with Advanced Security

Microsoft over the years has had security (be it file ACLs or firewall) where more specific rules override less specific rules - Instead of prioritization - So it would be reasonable to expect firewall is the same way - On file ACLs there's no prioritization - The logic is explained well in the Resource Kit - I remember seeing both the ordering AND logic for why this works better than prioritization for rules in one of the old resource kits (not sure what windows version).

One problem with firewalls with prioritization rules is I could accidentally put allow all at the higher priority and break my whole chain of rules. The same could happen here but it would be a little less likely IMHO.

As Jim B said, use a port based rule instead rather than an application rule,

Also check if there aren't other rules in you firewall settings that would superseed yours. This could be a application rule on deny that work on same port as your program.

You might also want to fire up Wireshark (http://www.wireshark.org/) to see what port are used to initialized the connection.

You can use http://packetlife.net/media/library/13/Wireshark_Display_Filters.pdf to be able to filter out packets you don't want.