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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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I haven't used PuTTY in a long time; have you tried with Dymanic instead of Local? I think the way it is now you're only forwarding :80. – zmode Oct 21 '12 at 14:21
    
@zmode - Sorry, the screenshot is incorrect, I actually used Dynamic in my real testing. – ripper234 Oct 21 '12 at 14:57
up vote 1 down vote accepted

I managed to pull this off by switching from PUTTY to command line SSH:

ssh -D 9998 user@myserver.com

or

ssh -ND 9998 user@myserver.com

(Not sure which one of these did it)

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I really do not understand why do you use dynamic port, but if it works for you, then fine – Serge Oct 21 '12 at 16:36

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?

That means that your socks proxy server is set not to connect clients to port 443. Check its configuration

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How? Do you mean some socks/ssh daemon running on the target (ubuntu) machine, or the PUTTY client (which is also a server) – ripper234 Oct 21 '12 at 16:26
    
The former one, the daemon on Ubuntu machine – Serge Oct 21 '12 at 16:32
    
I think this is not the case - check out my answer. – ripper234 Oct 21 '12 at 16:34

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