Hi guys! Just noticed this thread. I wanted to just chime in and support this idea. I think there is immense value to using normal e-mail over Tor and the e-mail client I am working on (Mailpile) is looking to support this sort of thing out of the box, including appropriate UI feedback so users can understand when messages are sent (or received) securely and when they are not (this is probably not a 1.0 feature, but it will be included in a later release).
We have written straw-man description of some of our ideas here: https://github.com/pagekite/Mailpile/wiki/SMTorP Aside from that I wanted to respond to Jonathan's comment from before: > In short, if you let your users send unencrypted messages in the same > client/system > as covert messages, your users won't be safe. And if you force encryption for > everything, you defeat the purpose of using email and should instead choose a > protocol/system designed specifically to hide metadata. In short, I disagree with this analysis. Although this may be true for the high risk users with well funded adversaries, most people are neither of those things. If the goal is to simply improve the privacy of as many people as possible, as much as possible, then an all-or-nothing attitude is extremely counterproductive. In Mailpile we are building an e-mail client that people can use today, to communicate with the vast ecosystem of insecure e-mail addresses that already exists. We want to gradually, opportunistically improve security whenever we can. If we exchange an insecure e-mail with someone, and their headers (or attachments) imply that we could upgrade to PGP, we should. If their mail also contains hints that we could switch to SMTP over Tor, then we should do that too. If this kind of thing is done in a seamless, convenient fashion with a clear UI that tells the user what is happening, then security can become a natural part of people's e-mail experience and maybe we can break the chicken-and-the-egg cycle of nobody using secure e-mail because nobody users secure e-mail... and that will benefit the high-risk users as well. We won't get there in one step though, we'll have to live with imperfect partial solutions for quite some time (probably forever). That's just the way things are. Cheers! - Bjarni -- Sent using Mailpile, Free Software from www.mailpile.is
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