[stebalien]

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 bounce, refusing to send any more notifications to that address. They since improved the situation and their support was actually very helpful and responsive here, but it's pretty clear that modern SMTP senders have an expectation that recipients will be "always online" that didn't exist when the protocol was invented.

[dijit]

I have a feature (called greylisting) whereby my server intentionally rejects the first mail it receives from a domain.

I have never had anyone claim that their mail has not been delivered to me, and I get a lot of mail.

Retry is built in to the spec, and if you’re really worried you can put a second “receive” SMTP server on the internet with a lower priority, and have it backhaul with LMTP.

———

Email was designed in a time where hosts were not perpetually connected to each other.

[Symbiote]

GMail itself will sometimes temporarily reject messages, then accept them later.

I have Postfix logs showing things like "this address is receiving a high rate of email" which are later accepted.

[logifail]

> 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...

[toast0]

> 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 (for most mail) when I gave up on self hosting 10 years ago, but it's plausible.

[Krei-se]

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 right it's totally doable.

Gives you actual private caldav too btw

[jasode]

>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.

[grepfru_it]

Until that one email you wish to send to someone important never goes through.

The fact is, big email providers have all the leverage and you will have to play their game ($$$) in order for your email to work everywhere.

It happened to me and that made me realize it's not worth the hassle. Good luck

[BikiniPrince]

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