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Self-hosting email like it's 1984

maxadamski.com

81–90 of 190 posts

Re: Self-hosting email like it's 1984

#81
I think the following is a better guide for someone looking for a complete setup that includes an IMAP server and that can be used with regular email clients like Thunderbird:

https://workaround.org/ispmail-bookworm/

I set up my own server more or less following the above guide, but eschewed the database in favor of plain text files. I wanted to keep things simple since I am the only user, but the above guide should scale to big enterprise setups.

Re: Self-hosting email like it's 1984

#82

(had to dug my comment from under a flagged parent) I self-hosted for well over 20 years, I did not throw the towel and I do not plan to. Self-hosting is a sign of pride. Neither my government nor my Prime Minister nor even my Ministry of Interior or Foreign Ministry can host their own email. Last time I checked, only State Security self-hosted. I was probably lucky, but I rarely had delivery problems. The last one w…

> treat self-hosting like a hobby and learn to enjoy it.

This is why I have stepped away from a lot of my self hosting. I have turned my attention/time elsewhere. Apparently though the time/money balance is shifting a bit again, so it may be worth it to go back.

My biggest hesitance to self hosting email specifically is dealing with spam. What does that look like these days and do you have any pointers to share?

Re: Self-hosting email like it's 1984

#83
post #74

I used to do this. What finally killed it wasn't reputation, it was the fact that I needed 100% uptime or risk losing messages, getting my address blacklisted, etc. Email is supposed to be resilient to down time (retries, trying each MX record, etc.) but I found that large mail providers tend to just bounce and walk away. Worse, GitHub (back in 2016 and 2018) would mark a recipient as "unavailable" after a single bou…

This is fearmongering. My mails always got resent after some hours or a day. It's absolutely NOT possible to tell if the problem is on your side, senders side or somewhere in between why a mail is not delivered once and no standard server config would simply toss it. Host your own mail. I get 99% deliverability with 0 repuation since i do dkim and spf correct. Don't be distracted by the "complexity" - if you config r…

>I get 99% deliverability with 0 repuation since i do dkim and spf correct.

Your anecdote of success doesn't matter to the others that correctly configured DKIM/SPF and still don't get their emails delivered to Gmail/Outlook/Yahoo/etc. E.g. : https://news.ycombinator.com/item?id=32715437

One of the reasons for hard-to-diagnose sending failures is that Gmail/Outlook have "extra invisible rules" that override correct DKIM/SPF settings because spammers and phishers also have correct DKIM/SPF. So they use extra heuristics such as "ip reputation" etc.

And even after one gets it working, e.g. "submit some form" to Microsoft and wait a few days to get things unblocked... the deliverability may break again because of another "invisible heuristic".

EDIT to reply: >No, that's because your relay overwrites part of the header which makes dkim strict break. Change to relaxed or don't modify the header on your relay.

Delivery reliability can still break without using a relay.

In fact, this unreliability of 100% self-hosting at home is why some self-hosters split it into a hybrid setup and add an external relay for outgoing SMTP and only keep self-hosting for receiving email.

Re: Self-hosting email like it's 1984

#84

Modern email providers, especially ones offered by ISPs often have the same problems that people criticize self-hosted providers for. Even Google has problems. For example, I regularly order via companies that use Shopify. Now, all of the shopify emails are going straight to spam in Gmail, despite constantly marking them as not spam. (These even pass dmarc/spf/dkim etc, so who knows what's going on here.) Email deliv…

Bizarrely, I also find Gmail's spam algo is actually oversensitive to marketing emails from companies these days, which I never thought was something I would complain about. But like you said its super annoying when I actually want the emails. Seems like we had the opposite problem 10ish years ago. But now the pendulum has swung a bit too far in the other direction. Ultimately most of the spam I get these days is act…

Microsoft Outlook has been flagging their own marketing emails as spam for me lately. I'm not sure if I ought to be impressed or disappointed.

Re: Self-hosting email like it's 1984

#85
post #26

Not sure why someone would go through the pain of cobbling up a self hosted solution based on Postfix when you have fully integrated solutions like https://stalw.art/ , which are a breeze to setup.

Postfix has been around for decades and respects the Unix philosophy of doing one thing and doing it well. It's perhaps the most widely deployed MTA, and as such it has been thoroughly field tested.

Also, people in the FOSS community tend to be wary of "open source" projects primarily developed by a commercial company under dual licensing.

Re: Self-hosting email like it's 1984

#87

(had to dug my comment from under a flagged parent) I self-hosted for well over 20 years, I did not throw the towel and I do not plan to. Self-hosting is a sign of pride. Neither my government nor my Prime Minister nor even my Ministry of Interior or Foreign Ministry can host their own email. Last time I checked, only State Security self-hosted. I was probably lucky, but I rarely had delivery problems. The last one w…

> I decided to finally replace my aging Debian jessie setup by Arch Linux, and I rewrote all cron jobs as systemd timers. Man, I wish I had 1% of the motivation I had 20 years ago to do something like this, before all the full time job, wife and child.

Stuff to keep you busy is always there, you can control what you spend the rest of the time on.

Re: Self-hosting email like it's 1984

#90

(had to dug my comment from under a flagged parent) I self-hosted for well over 20 years, I did not throw the towel and I do not plan to. Self-hosting is a sign of pride. Neither my government nor my Prime Minister nor even my Ministry of Interior or Foreign Ministry can host their own email. Last time I checked, only State Security self-hosted. I was probably lucky, but I rarely had delivery problems. The last one w…

I have been self-hosting for about 25 years. I remember the protection.outlook.com issue. Once there was an issue with a bank that tried to do encryption, but used an expired certificate. But once I told them what the problem was, and that it was a problem for paying customers, they actually fixed it.

Being able to check the server log can be very useful. E.g. to tell someone that their mail was delivered to a served using their domain name, with that IP-address at that time.

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