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Does anyone have success stories about self-hosting email, or is it all futile and I should just use a paid service like Fastmail? From what I've found online, self-hosting guarantees that I'll get on someone's spam list, and removing myself from it will require a ton of effort (if it's possible at all).

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@minoru i did, was pretty straightforward with postfix and dkim/stuff howtos

@L29Ah "Did", so you don't do it anymore? Why? Also, how long did you keep it up, and what did you replace it with?

@minoru Used to host it on my home box, but i don't have a home with a box anymore, so i'm just using riseup.net for personal mail.

@L29Ah @minoru I still self host, dkim solves spam issues.

@nm0i How long do you do it? Where is the server hosted - are you using a residential IP, or is it in a cloud somewhere? Have you ever gotten in any blocklists, was it hard to get yourself off them?

@L29Ah

@minoru @L29Ah 11 years, london, cloud, got on mail.ru blocklist, got out because one of admin duders was on irc

@L29Ah @minoru Same here. With a proper security configuration I had no issues over recent years with my personal email.
I use some cheap 128MiB Ram vps box. Nothing fancy.
I think that’s because when everything is properly signed from DNS to IPs then probability that our emails are fishy is negligible.

@kmicu

when everything is properly signed from DNS to IPs

So not just SPF and DKIM, but also DNSSEC and DANE?

@L29Ah

@minoru @L29Ah I can only confirm that based on my setup with SPF+DKIM+DNSSEC and no DANE (I was to lazy to set it up yet) everything works. No issues with emails transfer with gmail et al.
I migrated from gmail years ago to that very setup.
My mail is under .cz if that makes any difference 🤷

@kmicu That sounds much more reassuring than what I've read elsewhere. Thanks!

@L29Ah

@minoru It's not overly difficult. If you are just doing personal email then you likely won't end up on a spam list. The issue is that with email you don't know there's a problem until people haven't been getting your email (or you haven't gotten any) for like a year and you finally notice. It's not that it's hard, it's that problems are quiet.

Even as someone who knows how to self-host email (I worked for an ESP for a while), I'd still just use a paid service so I don't have to deal with it.

@minoru I've been selfhosting my email for the past 15 years, and I can tell it is way easier now :)
Still require work and maintenance though. Sometimes also some action to get remove from blacklist, but that happened only 2 times for me…
There are already a lot of packaged things for people starting email hosting like mailcow, yunohost and others :)

@bacardi55

Sometimes also some action to get remove from blacklist, but that happened only 2 times for me…

That's the part that scares me the most. I don't want to suddenly find out that my emails stopped getting delivered a few weeks ago.

2 times in 15 years doesn't sound so bad though, I could live with that.

@minoru Well, it happened this year (the 2nd time) and basically took me 30min to fix (but only 2 days after so that may be a problem)…
But yeah, when I found out it was not something I wished happen for sure.
I won't say it's worth it or not because it really depends on you at the end…
Also, having other users like family makes it a bit more painful as they just expect stuff to always work^^

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