Tunneling HTTPS traffic via a PUTTY/SSL tunnel with SOCKS

Posted by ripper234 on Super User See other posts from Super User or by ripper234
Published on 2012-10-21T14:11:50Z Indexed on 2012/10/21 17:05 UTC
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Filed under:

putty

|

https

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socks-proxy

I have configured a SOCKS ssh tunnel to a remote proxy, and set my Firefox to use localhost:<port> as a SOCKS proxy. My intention is to tunnel outgoing HTTP/S connections from my machine via a specific 3rd party server I own (on AWS).

In my testing, HTTP UTLs are forwarded properly (e.g. when I access http://jsonip.com/ from my computer I do get the server's IP)

However, whenever I try to reach an HTTPS address, I get this error:

The proxy server is refusing connections

How do I debug/fix it?

My PUTTY tunnel config is simply (some random source port number + dynamic checked):

enter image description here

P.S. I'm aware I might need to manually accept SSL certificates. The reason I'm doing this is to resolve problems using gmail as an outbound SMTP service.

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