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Self-hosting email like it's 1984

maxadamski.com

121–130 of 190 posts

Re: Self-hosting email like it's 1984

#121

I've been self-hosting my email for over 10 years now (I'm going to link a bunch of my old comments on old email HN threads). I have fallen back to using Amazon's SES to send because all of Digital Ocean's IP blocks suddenly got marked as bad and I don't have enough volume to improve a new IP reputation - https://news.ycombinator.com/item?id=39891262 , https://news.ycombinator.com/item?id=38471262 I use Gmail as a fr…

Long winded admission that you might as well pay for google's email service.

Re: Self-hosting email like it's 1984

#122
I at least maintain administrative control while using free resources. I looked at the completely self hosted route a long time ago and didn’t want to deal with that. Fast forward to today and I’m dealing with a friend who has the polar opposite. Now their mental faculties are reduced and they lost devices. Couple this with not paying previous management entities and it’s a digital lock out. Recovering from this is a nightmare and I’m operating blind. For a normie this would be impossible.

Re: Self-hosting email like it's 1984

#123

I've been self-hosting my email for over 10 years now (I'm going to link a bunch of my old comments on old email HN threads). I have fallen back to using Amazon's SES to send because all of Digital Ocean's IP blocks suddenly got marked as bad and I don't have enough volume to improve a new IP reputation - https://news.ycombinator.com/item?id=39891262 , https://news.ycombinator.com/item?id=38471262 I use Gmail as a fr…

Long winded admission that you might as well pay for google's email service.

And use it only for important things that won't be delivered if you don't send them from Google.

Receive only (e.g. account signup)? Use your own account. Not important anyway? Use your own account. Your recipient needs the email more than you? Use your own account. None of the above? Use a mainstream provider for that email only.

Re: Self-hosting email like it's 1984

#125

I've been self-hosting my email for over 10 years now (I'm going to link a bunch of my old comments on old email HN threads). I have fallen back to using Amazon's SES to send because all of Digital Ocean's IP blocks suddenly got marked as bad and I don't have enough volume to improve a new IP reputation - https://news.ycombinator.com/item?id=39891262 , https://news.ycombinator.com/item?id=38471262 I use Gmail as a fr…

Long winded admission that you might as well pay for google's email service.

Not really, I don't send many emails these days but find the ability to filter and run automations on emails coming into my server very useful.

Not to mention I use a separate email per service so I can tell if there's a data breach (usually end up seeing an uptick in spam).

*Edit: Not to mention I can pay for a relay service other than Amazon SES without using Google's services, and for significantly less.

Re: Self-hosting email like it's 1984

#126

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…

I know right. It’s like, “what did they do to my boy?” as to huddle over the bullet ridden corpse of your son.

Re: Self-hosting email like it's 1984

#127

Earlier quoted context omitted.

Long winded admission that you might as well pay for google's email service.

And use it only for important things that won't be delivered if you don't send them from Google. Receive only (e.g. account signup)? Use your own account. Not important anyway? Use your own account. Your recipient needs the email more than you? Use your own account. None of the above? Use a mainstream provider for that email only.

But this is why I'm using Amazon's SES for sending my very low volume emails now. It's never been blocked, if they ever start causing me grief I can switch to a new email relay service in a matter of minutes if necessary.

Re: Self-hosting email like it's 1984

#128
> "If something isn't working for you, please double-check your DNS records, and triple-check that TLS certificates are readable by the Postfix user, and that DKIM keys are readable by the OpenDKIM user. Postfix and OpenDKIM logs will also be useful. The OpenDKIM config file is especially unforgiving of typos, so watch out for small mistakes!"

I tried this over a period of years, aggressively changing my email server configuration as new challenges appeared, before realizing the basic problems were (a) a server's configuration is a moving target that requires constant revision, and (b) if your ISP has ever hosted a spammer, even briefly and inadvertently, then its entire address block may be universally blacklisted and you have to change ISPs, possibly several times.

So ... I gave up. If I had nothing better to do, if I just wanted to play email server whack-a-mole, that would be different, but I have a life apart from pleading with giant email recipients to trust my little server.

It's not as though Google, Microsoft, et al. have an incentive to trust small email servers -- quite the opposite. They can -- and do -- make the argument that they shouldn't trust anything but another big player like themselves.

Re: Self-hosting email like it's 1984

#130
post #82

Earlier quoted context omitted.

> 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?

I’m not sure that there is any pre made product for this, but I’ve been playing around with LLMs to identify spam, or just generally sorting emails for you. And even the self hosted models seem to be pretty good at classifying emails even without external information like spam blacklists or IP reputation.

I think LLMs, even local ones, are probably way overkill for identifying spam or sorting/classifying emails.
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