Jumping headfirst into security- noob question about email servers

General Tor and Anonymity Talk
1

I’m sure there are more appropriate places to ask this, but I just started using whonix and while I’m here I thought you guys would know how to help with this. If you’ve got a few minutes to explain it to a noobie I’d really appreciate the help.

I want to send and receive email @ my own .onion address. If I understand correctly hosting a hidden service is a simple as running the web server as normal for clearnet and then pointing tor at it. But are there extra complications for email? I know it’s a weird old protocol. Can I just run my MTA/MDA on the server as normal? Someone said something about pointing my email server applications at SOCKS? How would I do this?

Thanks a ton in advance for any help!

p.s. I know pointing a MUA like thunderbird at onion email is tricky, that’s okay, webmail is fine.

2

An important thing to consider. If this setup succeeds at all, you would only be reachable by people who are using Tor and/or who are using mail servers that also are talking Tor.

Someone from clearnet couldn’t send you an e-mail. Just as clearnet users cannot browse .onion addresses. There are services such as tor2web, but it’s “2web”, not “to e-mail” or “to anything”.

Have you considered this?

3

I understand. I’m fine with that.

4

Ok.

Have you considered alternative to hidden services? Those are listed here:

They might work better.

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But if you want only Tor to Tor communication, I mean who many people have such an obscure setup… Why e-mail?

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Using Tor hidden services it could be difficult. Because e-mail usually require MX DNS. Tor does not support those yet. (Support all kinds of DNS over Tor (#7829) · Issues · Legacy / Trac · GitLab) I am not aware of someone having done this setup.

Mixmaster is similar to e-mail. When I documented it back then, this was quite difficult. You might find some interesting pointers here:

There might also be relevant information here:

Onioncat might help (all parties need this, but in your setup, all parties need that anyhow):
https://www.whonix.org/wiki/OnionCat

You can also try asking on the tor-talk mailing list since this is mostly Whonix unspecific.

After having written this, I just typed “e-mail onion” into Google. Did you try that? Found this pdf, didn’t test:

5

Oh, wow, that pdf looks great! Just what I was hoping for. I’ll try to puzzle through it, but in the meantime do you have any sage advice about it? Or (dare I ask) would you be willing to sit in a chat with me and hold my hand through setting it up? At the risk of being crass I could pay a bit of BTC for your time.

Edit:

I just found this: Petter Reinholdtsen: A Debian package for SMTP via Tor (aka SMTorP) using exim4

It looks really promising- what do you think? Should I be able to do this on whonix?
I feel very close to understanding this myself, but I’m just not quite there.

6

No, sorry, I don’t think I will have time for that.