I've been finding some problems with Skype when combined with TProxy and HTTPS interception and wondered if anyone had seen this before:

Skype works so long as HTTPS interception is not performed and traffic to TCP and UDP ports 1024-65535 is allowed directly out to the internet. Enabling SSL-bump seems to break things - When making a call, Skype makes an SSL connection to go.trouter.io, which Squid successfully bumps. Skype then makes a GET request to https://go.trouter.io/v3/c?auth=true&timeout=55 over the SSL connection, but the HTTPS server responds with a "400 Bad Request" error and Skype fails to work.

The Skype client clearly isn't rejecting the intercepted connection since it is making HTTPS requests over it, but I can't see why the server would be returning an error. Obviously I can't see what's going on inside the connection when it isn't being bumped, but it does work then. The only thing I can think is maybe the server is examining the SSL handshake and returning an error because it knows it isn't talking directly to the Skype client - but that seems like an odd way of doing things, rather than rejecting the SSL handshake in the first place.

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