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How should one best access Google communications and social services, like Gmail, Talk/Hangouts, and maybe G+ over Tor?

I'll propose the default threat model for interacting with Google as : We've only one non-temporary identity with Google. Google should never connect web searches or maps queries with this identity. Google should never learn our location either.

We could access Gmail and Gtalk by asking the Tor browser bundle for a new identity, but that's error prone and prompts CAPTCHAs.

Instead, we could make our exit node constant for Google by running a second Tor on port 9050 with the config lines :

MapAddress *.google.com *.google.com.foo.exit
MapAddress *.gmail.com *.gmail.com.foo.exit 

And access Gmail via IMAP/SMTP and Gtalk via XMPP instead of the Tor browser bundle. We cannot make our exit node constant for the Tor browser bundle in this way because we might wish to use Google search.

In this setup, there remains some risk of CAPTCHAs since foo.exit is a Tor exit node. We must therefore point a browser at port 9050 at least occasionally. And we might want G+, Google Groups, etc. too.

A priori, I'd do this by creating a second profile in the Tor browser bundle that uses 9050 instead of 9150 and disables Tor button? What else should we do? What else have I missed?

How should one select foo.exit? Just pick an exit with solid bandwidth and uptime from the list of tor exit nodes? Attempt to pick an exit with several alternative exits in the same city?

Does MapAddress support IP address ranges? I could imagine it doing so with a syntax, like MapAddress 64.233.160.0-64.233.191.255 *.foo.exit, but afaik nothing like that works.

Also, I presume the same MapAddress trick cannot realistically be used for financial institutions, like PayPal, unless we've a private exit node that never appears in the consensus, right?

  • As an aside, we might want a torrc tag on tor.SE, maybe an alias to configuration, maybe not. – Jeff Burdges May 10 '15 at 23:01
  • Appears one must open and password protect the control port on the system Tor to do the above. I donno if there is a realistic option for making TorBrowser profiles spawn a new tor daemon, but sounds messy. – Jeff Burdges May 11 '15 at 20:22
  • This may work but I wanted to suggest not doing this as it increases your threat of de-anonymizing attack since you would so constantly be using the same exit. Instead, look into VPN/proxy services as the final exit. so it's Client>Tor>VPN/Proxy>Google service – Lizbeth May 19 '15 at 21:07
  • We're using a second tor demon, and a second browser, so normal TBB traffic that accesses google services won't be associated. In practice I wasn't about to make this work because google still asks for CAPTCHAs. I'd need my own secret exit node to make it work. I'll just dump gmail and gtalk instead. – Jeff Burdges May 19 '15 at 21:12
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    It's actually trivial to quit gmail, just forward the mail to another account. I donno if there are forwarding options for XMPP but oh well. – Jeff Burdges May 19 '15 at 21:17

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