While the accessing of the GMail web interface via Tor in Firefox with Torbutton installed seems simple enough, you might prefer to use an email application with GMail, in which case it might seem a bit harder.
Here’s how.
Install Stunnel which you get here. Once you have, find in Start | All Programs | stunnel | Edit stunnel.conf which on selection opens Notepad with the stunnel.conf file ready.
Insert these lines:
[SMTP Gmail]
accept = 127.0.0.1:25
connect = smtp.gmail.com:465
[POP3 Gmail]
accept = 127.0.0.1:110
connect = pop.gmail.com:995
and then File | Save and you’re done there. DO NOT run Stunnel from the Start Menu or it is going out straight from your IP.
Instead, using SocksCap which you already downloaded and installed earlier, you start that and go to File | New… and here’s the values:
Profile Name: Stunnel by Tor (or whatever you prefer)
Command Line: "C:\Program Files\stunnel\stunnel.exe"
Working Directory: "C:\Program Files\stunnel\"
and click OK.
From within SocksCap you now run Stunnel AFTER starting Tor from the Vidalia Control Panel. I suggest letting it run a few minutes to build a few circuits before starting Stunnel.
Now simply aim your email application at Stunnel. Where you enter your POP3 server, user 127.0.0.1 and the same IP address for your SMTP server. Enter your GMail account user and pass information and save everything.
What this does is to cause your email application to send standard POP3 and SMTP traffic at Stunnel which receives it and relays it to GMail’s servers which only use SSL but many email applications don’t, and does it via SocksCap's redirection towards Tor.
This saves you from trying to get SSL functioning on the email application, which while it might work almost certainly won’t be SOCKS aware and thus will be unable to be directed at Tor. IF your email application IS SSL aware, then theoretically you could start it within SocksCap and cut out Stunnel. Of course, many aren’t and for those who don’t want to dick around with the SSL stuff and just insert the easiest values to use, then this method works.
Also, it helps familiarize yourself with using Stunnel to use SSL with non-SSL-aware applications AND do it with Tor.
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