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Self-hosting email like it's 1984

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Re: Self-hosting email like it's 1984

#151

Post by man8alexd »

crossroadsguy wrote: post #141

Where do people self-host these emails? When email self-hosting is talked about, my thoughts wander to Fastmail, Migadu, etcetera (I use one like these), but I quickly realise that's not it. On those lines, I do not believe these mail self-hosting folks are talking about some VPS, or server from some provider, or even AWS, et al., either — not self-hosting enough. It must be a computer/server always running at their…

The problem with self-hosting is finding an IP with an clean reputation and not on any block lists, with good neighbours (people sometimes block /24), with an open outgoing port 25. Then you'll need to slowly warm up this IP for weeks or months.

Re: Self-hosting email like it's 1984

#152

Post by Biganon »

jasode wrote: post #83
Krei-se wrote: post #74

Earlier quoted context omitted.

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 D…

I hate the fact that your comment got flagged / greyed out / whatever even though it's perfectly correct. I'm one of those people who had configured everything perfectly. Score of 100 on mail-tester, SPF, DKIM, DMARC, you name it. Examining the headers in an e-mail sent to gmail: pass, pass, pass. Everything green.

Microsoft however? Denied, 100% of the time. Spam folder, or even plain rejected. Why? No idea, they won't say. They redirect you to their shitty partner that you can PAY in order to HOPE you get approved.

I don't know why our experiences are considered "anecdotes", and not the other way round. What's the incentive for big players to accept e-mail from home servers or small dedicated servers? "Sure it could be Standard Nerd from HN running their own stuff for street cred points, or it could be one of the bazillion spam factories sending fake UPS scams. In doubt, let's reject."

Re: Self-hosting email like it's 1984

#153

Post by qingcharles »

rmoriz wrote: post #137
qingcharles wrote: post #124

How big a deal is reverse DNS for this and anything else in 2025? I've not created any PTR records for anything for about 20 years now...

No deal, even possible for ipv6 easily with eg Hetzner, Vultr

Thank you. I'm hosting all my boxes with Hetzner. The option is right there and I never knew. Might as well add it.

Re: Self-hosting email like it's 1984

#154

Post by 6ak74rfy »

drnick1 wrote: post #85
lifty wrote: 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.

As for your second paragraph - I am more worried about the project being maintained by more or less a single person.

Re: Self-hosting email like it's 1984

#155

Post by isodev »

sam_lowry_ wrote: post #57

(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…

It’s amazing how today we have social networks bending backwards to be able to call themselves “open” and “decentralised” when we already have all the tools we need to be truly independent.

I think when we’re building something with “good UX” the major point of “does this remove agency from users” is somehow missing from the picture. When everything runs on some kind of system, it’s not extraordinary to expect people to know how it works and maybe be able to do it themselves.

Otherwise, fast forward a decade of simplifications, and we can’t even install an app without someone on the other side of the world approving the “transaction”.

Re: Self-hosting email like it's 1984

#156

Post by dugite-code »

defanor wrote: post #133
dugite-code wrote: post #120

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…

I missed an incoming message (fortunately an unimportant one) from Amazon SES recently, since its 54.240.27.30 address was listed by bl.spamcop.net: Amazon kept trying different addresses while running into greylisting, until it tried that address and was rejected. Possibly it is less of an issue when sending between large providers (e.g., Amazon to Gmail), but apparently still not a perfect solution to ensure messag…

Sure but it really highlights that even big providers get black balled at seemingly random. I've had an email from a Microsoft email address come up in a spam list before. No one is safe.

Re: Self-hosting email like it's 1984

#157

Post by stavros »

tolciho wrote: post #142
stavros wrote: post #101

Earlier quoted context omitted.

I'm thinking of self-hosting email sending for my applications. Does anyone know if, with DMARC/DKIM, email reputation moved from the IP to the domain? If I can make sure only my server can send mail from my domain, shouldn't the sending IP then be irrelevant?

The sending IP remains very relevant; it may be in a third-party blacklist (RBL) or site local blacklist due to prior spam from said IP or even nearby IP(s). Let's have a look through /var/log/maillog... okay that didn't take long. $ rubbled 86.54.42.238 86.54.42.238 zen.spamhaus.org. XBL (exploit) 86.54.42.238 zen.spamhaus.org. 127.0.0.9 86.54.42.238 zen.spamhaus.org. SBL (spammers) Spammers can setup DMARC, and hav…

Oof, thanks, I'll keep paying someone then :(

Re: Self-hosting email like it's 1984

#158

Post by aborsy »

If you host your email on a VPS, you might as well let an email provider manage it all for you. In both cases, a company has access to your emails. What you have achieved is doing the dirty job of administration for the company, while not getting the privacy benefits of self hosting.

If you host it at home, can you endure uptime?

Re: Self-hosting email like it's 1984

#159

Post by jasode »

Biganon wrote: post #152
jasode wrote: post #83

Earlier quoted context omitted.

>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 D…

I hate the fact that your comment got flagged / greyed out / whatever even though it's perfectly correct. I'm one of those people who had configured everything perfectly. Score of 100 on mail-tester, SPF, DKIM, DMARC, you name it. Examining the headers in an e-mail sent to gmail: pass, pass, pass. Everything green. Microsoft however? Denied, 100% of the time. Spam folder, or even plain rejected. Why? No idea, they wo…

>I hate the fact that your comment got flagged / greyed out / whatever even though it's perfectly correct. [...] I don't know why our experiences are considered "anecdotes", and not the other way round.

It's because people who successfully self-host think their situation universally applies to everyone.

Here's another example from 2017 of someone replying to my previous reasonable comment about self-hosting by overconfidently saying I was exaggerating the issues : https://news.ycombinator.com/item?id=15526127

And then 18 months later in 2019, that same person reveals they also got their sent emails rejected by Gmail : https://news.ycombinator.com/item?id=19757607

So they end up solving it by "outsourcing" the outbound email to a relay (SendGrid).

So my comment gets downvoted for explaining what others had to do in the real world.

The following should not be a controversial statement but for some reason it is: Correctly configuring SPF/DKIM/DMARC and getting 100% green score on https://www.mail-tester.com/ for your self-hosted setup ... does not universally mean your outbound email will get accepted by all the services.

Re: Self-hosting email like it's 1984

#160

Post by logifail »

toast0 wrote: post #73
logifail wrote: post #72

Earlier quoted context omitted.

> it was the fact that I needed 100% uptime or risk losing messages Q: If your server(s) is/are offline for a few hours, why would you "lose messages"? I've just checked my own email server -> "up 219 days" Honestly, compared with the stuff we do all day, this is not hard ...

> Q: If your server(s) is/are offline for a few hours, why would you "lose messages"? They said... >> 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. I take that to mean that if your server isn't availble to receive the mail at the time it is first offered, it won't be retried later. That wasn't the case (fo…

> I take that to mean that if your server isn't availble to receive the mail at the time it is first offered, it won't be retried later.

Umm, RFC 5321, which describes queuing and retry? SMTP is designed to be very forgiving of transient network issues.

> That wasn't the case (for most mail) when I gave up on self hosting 10 years ago, but it's plausible

Plausible? To those of us who run our own mailservers, the OP's statement is an extraordinary claim.

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