Ask HN: how do you manage encrypted email?

8 points

13 years ago

I've recently (re-)decided to make an effort to use PGP, and to convince others to use it too. (My effort to do so: http://www.ocf.berkeley.edu/~rwl/encryption.html, linked from my .signature.) But I've run into a couple of problems fairly quickly. If you use PGP regularly, how do you solve them?

1) Reading encrypted mail that I sent. If I need to remind myself what I said to someone, or recover an attachment, etc., I can't, because the only copy of my message is encrypted with the recipient's public key. I could work around this by Bcc'ing myself on every message, but that would have the mildly annoying effect of duplicating all my outgoing messages; every time I were to look for a message I sent to Mr. X, I'd get two results, and I'd have to figure out which one was encrypted with my key to read it.

2) Search. The more serious issue is that I can't search encrypted email, whether I sent it or received it. It is conceivably possible to search mail encrypted with my public key by decrypting it before running the search (though not encrypted mail that I sent, pending a good solution to problem 1). However, that seems like it would be extremely slow in practice, and I am not aware of any software that would make this simple or practical.

I am currently using Mutt as a client for a local Maildir, with offlineimap and notmuch to download and index my mail, but I am willing to switch to a different setup if there is one out there that solves these problems. What's frustrating is that both problems seem pretty obvious, and solutions are conceivable, but search results for practical solutions elude me.

I don't want to recommend to others that they use PGP if it means they cannot reasonably search their mail archive and read their sent messages. What should I tell them to do?

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