this post was submitted on 07 Nov 2023
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Clients like Thunderbird are great because you have everything stored locally so you can easily search offline. They also support encrypting and decrypting emails in PGP. However, they seem to have the same limitation as protonmail where you can't search through encrypted emails.

I know that protonmail can't just store your key at their server since that would defeat the purpose, so the emails are all ciphertext to them right? But in Thunderbird, you already have the key and decrypt everything all the time. So why can't you skip the middleman in your local machine and store everything locally in plaintext? It's not less secure since if your local machine is compromised, your private key is also compromised.

Or at the very least give us the option and have a slightly less secure but much more convenient option.

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[–] pianoplant 8 points 1 year ago (1 children)

I've been trying to move away from email as a document server.

Anything that's important / I might want to reference later gets exported to a secure paperless-ngx instance where it's neatly categorized and easily searched. I then delete it from my inbox.

[–] [email protected] 5 points 1 year ago (1 children)

Came here to ask about paperless and the myriad of versions, even though it's off topic.

[–] pianoplant 7 points 1 year ago (1 children)

Paperless-ngx installed via docker-compose is super easy. I have it on a luks-encrypted vm only accessible via tailscale.

[–] [email protected] 2 points 1 year ago

Thank-you. I'm really interested in finding a way to make searching my paper much easier.

[–] [email protected] 6 points 1 year ago* (last edited 1 year ago) (1 children)

If you're in Linux, you can use eCryptfs to setup a private encrypted directory, move the ~/.thunderbird directory into it and just leave a symlink to it in your unencrypted home directory. Then you can store your emails in plain text in the encrypted private directory.

It's not even complicated to set up: most Linux distributions are setup so that the private directory is automounted upon login: when you're not logged in, your data at rest is encrypted. It only becomes readable when you're logged in.

Both my Thunderbird and Firefox directories are stored in my private directory.

[–] [email protected] 5 points 1 year ago

This does not answer the question. OP wants to Thunderbird to decrypt PGP mails. Yes, it makes sense to use an encrypting fs, but we are still missing this thunderbird feature.

[–] tpWinthropeIII 3 points 1 year ago (1 children)

Locally, an attacker still needs to know your password. A strong password can make it too expensive or impractical to brute force.

[–] [email protected] 1 points 1 year ago

Do you have to put in your password on every session in protonmail? If not, then that means that either the key is unencrypted and is stored somewhere else as plaintext or the password is stored somewhere also as plaintext, which would defeat the purpose.

[–] [email protected] 2 points 1 year ago

Honestly, I can't think of a good reason. This is just how email has always worked. What Thunderbird stores locally is identical to message on the server. It's not decrypted because no conversion happens when syncing mail.

I agree, it would make sense to keep plaintext emails locally or on a trusted server for practical reasons.

[–] [email protected] 1 points 1 year ago

This may be a long shot, but it's what I do, so it might be an option: Set up a crypto gateway like CipherMail which will automatically decrypt inbound email and sign/encrypt outbound. The result is that your Thunderbird will never get to see an encrypted email, decryption is handled transparently before it hit's your inbox. Obviously, if you don't trust your email provider, this is not an option.

This isn't simple and hence not for everyone, also comes with dependencies on your email provider, but it works flawless for me ever since I set it up. I run my own email server, hence adding in CipherMail wasn't a big deal.

[–] [email protected] 1 points 1 year ago* (last edited 1 year ago)

I think Tutanota (or just Tuta now?) does this, since search works correctly.

I think not using PGP helps Tuta a lot with this, since PGP is really outdated and does not play well with modern features.