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this post was submitted on 15 Sep 2023
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Technology
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What the fuck is wrong with email now ?
It's one of the only things that hasn't been ruined those past few internet decades, only slightly improved, and is still decentralized and can still allow you to self host, don't you touch it
Hard to selfhost and no E2EE by default I guess. First one can be blamed on Gmail and OutLook, second one is lack of mass PGP usage.
Gmail is actually relatively chill accepting stuff from self-hosted MTAs, even new ones the IP of which hasn't established a reputation yet
Outlook is indeed rougher but none of them even come close to the awfulness that are Apple / icloud email servers
Hard to self host is one of those things that has now become received wisdom in tech circles. It isn’t hard to self host email. More people should do it.
Exactly right. I keep reading this and I never know how to respond, it really isn't that hard and it's worth it. I've posted this before here but personally I go with a postfix+mariadb+dovecot+postfixadmin+spamassassin+opendkim stack; it's extremely easy to set up (if you read the docs) and it has suited me perfectly. Once it's configured it's rock solid
Beyond the obvious privacy advantages, being able to generate an email alias at any time (to the point where you can create one dedicated for each shitty thing you subscribe to) is also very useful for spam protection / infinite free trials and the like. Also aliases redirecting towards many recipients for easy organizing / mailing-list-like behaviour
PGP itself is a bit of mess.
For one thing, there's really only one major/popular implementation of it these days, which is GPG. The codebase is arcane. Pretty major security vulnerabilities pop up constantly. It doesn't have stable funding. Several years ago the entire project almost collapsed when the world discovered it had been maintained for several years by a single person who didn't have any time or money to maintain it. The situation is a little bit better now, but not much.
(For this reason, people are starting to use age instead of gpg, as the code is much smaller, cleaner, forces safe defaults, and doesn't seem to have security problems)
But the bigger problem that was never properly solved with PGP is key distribution. How do you get somebody's key in the first place? Some people put their keys on their own personal (https) webpage, which is fine, but that's not a solution for everyone, and doesn't scale very well. Okay, so you might use a key server, but that has privacy implications (your identity is essentially public to the world) and centralizes everything down to a handful of small "trusted" key servers (since there would be no way to trust key servers in a decentralized way). We should probably just have email servers themselves serve keys somehow, but nobody's put that into the email standard protocols.
The fact that keys expire amplifies all the problems with key distribution, and encourages people to do really unsafe things with keys, like just blindly trust them. You can sign other people's keys for them, but that also does not scale very well.
The key distribution problem is something that things like Signal have "solved" with things like phone number verification, but there's really no clear way to solve it on something totally distributed like email.
It's unencrypted
Is it encrypted while in transit between servers?
The answer is almost universally "no", if you didn't encrypt it yourself and are sending a cross-domain mail
I'm fairly sure connecting over TLS was the default last time I set up my server. But of course that only protects it from people snooping on the wires.
Yes, but that's almost certainly you connecting to the pop3 server (usually indeed provides TLS), or the server connecting to a dedicated smarthost for delivery (sometimes does as well). But mail exchange between MTAs that don't use smarthosts but reach the MX destination directly is mostly unencrypted, through port 25