Experimenting with Tor

I own an old, beat-up laptop I name ‘Venus’, from circa 2005. And with this laptop, I am exploring the fantasy that it should be configured to connect to the Internet, entirely using ‘Tor‘. I am trying to replicate what the TAILS USB-stick is said to do, but in the hopes that my own achievements will be more credible. You see, I doubt that TAILS really accomplishes what it claims to accomplish.

I have to admit, that I really have no idea, what that old laptop is supposed to do, once it is connected via Tor. This just seems like a fun project. And, there exist few services today, which will just let people connect via Tor. What one can do is browse, using a Web-browser, and not use Google, because the geolocation services of Google tend to blacklist most of the exit nodes of Tor.

But, wanting one additional ability, I also decided that Venus should connect to a less-important email server of mine via IMAP, and through Tor. What I discovered, was that the email client I was using for this does not itself support a Socks 5 Proxy, through its own GUI. And so I read that some command-line utilities exist for Linux, which will force the programs specified to use such a proxy.

The first utility I tried was called ‘proxychains’. But there is a caveat with this utility, that people fail to point out. It will negotiate the email client to connect to Port 143 in plain-text, rather than in cipher-text. I had not noticed this, until my laptop had connected to my email service, in plain-text in fact. This means that a corrupt exit node would have been able to sniff my password.

This is the full extent to which I was compromised. There was really no other sign, that anybody might have tried to connect to my (subscribed, paid-for) email server, in my place. But such a single exposure was more than what I was willing to let sit.

So I immediately changed the password of this subscribed, paid-for email service, to a much harder password, before anybody else got the chance, and I am still able to use that email address fully.

But then the question lingers in my head, of how I might nevertheless connect to it via Tor. There exists another command-line utility named ‘tsocks’, which claims to tunnel all the TCP/IP connections of its designated program, through the Socks 5 Proxy, without analyzing what types of authentication may be taking place.

I tried to use tsocks as described, but only found the comforting message, that the stream could not reach the IMAP server in question. So here there was no evidence that the utility in question actually breaks TLS encryption.

But ultimately, I would still not feel comfortable using tsocks, after the experience I had with proxychains, because I need to take the idea that tsocks does not break encrypted protocol, entirely on the words of software-authors who I cannot ultimately trust. These are Tor specialists after all. Even tsocks might eventually compromise my connection-security, even though it is not supposed to.

And so my little Tor laptop remains useless, from any practical perspective.

Dirk

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