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I use Sidestep on Mac OSX to make a proxy connection via SSH to an EC2 instance whenever I'm on public unsecured networks. In cases where the network has a more restrictive I can connect my IRC client to IRC networks like Freenode by configuring the client to use the local SOCKS proxy that Sidestep creates (which it does via ssh -D) but for servers requiring SSL this doesn't work.

Is there anything I can try for using the proxy when SSL is required or do I need to connect to / run a VPN?

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As a followup, I removed Sidestep from the equation. I blocked all traffic to IRC ports on my router and confirmed that normal connections would not work. Then I created a SOCKS proxy via SSH: ssh -CND 1080 me@thehost I confirmed that connecting to Freenode worked via the proxy. Connections to IRC servers requiring SSL still don't work. A paste of the SSH debug output showing my client attempting to connect to a couple of SSL-secured networks: – Brian Luft Jun 1 '13 at 4:09
up vote 1 down vote accepted

Turns out it was the Textual IRC client. Upgrading to v3 resolved the problem. I can now connect to SSL secured IRC servers.

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