When I last looked into setting up my own email server, I read that your messages ending up in the spam folder was almost inevitable if the receiver is using a major host (Gmail, iCloud etc.)
Is that still an issue?
Is that still an issue?
SPF and DKIM are pretty much required now, as are TLS/SSL. From there, it turns into a dice roll. Gmail is terrible about this; they have a totally opaque and very frustrating engine that sometimes filters messages into a junk folder and sometimes doesn't. Outlook.com uses a somewhat more traditional internal RBL, but they are happy to block network segments and they don't offer any way to query their blacklist or request removal from it, so you could do everything right but a neighboring VPS or IP will get you blacklisted anyway. Comcast will simply accept delivery of messages and then disappear them depending on an arrangement of the stars that I haven't quite figured out yet. And those old sbcglobal/Yahoo services users... just, uggghh.
A popular solution is to rely on a third-party service to handle your outbounds. Sendgrid specifically is really bad, they carry way too much junk traffic, so don't go with them if you decide to try this out.
I have a post banging around in my head that's titled "Email is fractally broken", and getting outbound non-spam messages to reliably land in other people's inboxes would be a significant part of that writeup.
In their activity feed right now, SendGrid traffic is being blocked by comcast, GoDaddy, iCloud, and a cornucopia of smaller services.
Here's one of SendGrid's outbound IPs, listed on multiple RBLs used by other services: https://mxtoolbox.com/SuperTool.aspx?action=blacklist%3a167....
On the receiving end, I've had to deal with waves of spam from SendGrid for years, and it's especially difficult because they carry a mix of spam and legitimate traffic, so blocking them causes complaints and not blocking them also causes complaints.
Never had any issues with sending mail. But I've been careful with the initial setup and have all the expected requirements covered : no open relay, SPF, DKIM, reverse ip, TLS,...
Been using the tutorial at workaround.org as basis for building the stack (postfix, dovecot, rspamd,...) and, while the initial learning curve was high, once its been set up, its been a really very stable setup requiring practically no maintenance whatsoever.
Not saying that's for everyone, just saying it works for me.
I guess I was lucky at the dice roll mentioned by other comments.
Ah yeah, and testing your outgoing emails using a service like mail-tester.com is very very useful. I aimed for and reached a perfect score 10/10.
So prereqs - 1) Valid reverse DNS on your sending IP. Preferably with a hostname that is also forward resolvable. 2) SPF Records 3) DKIM
I do in fact want this. It may not be possible, but I definitely want it to be.
(I eventually went with a Tutanota account, fwiw)
I have had my own email server sending emails which were not marked as spam. also I have had cases where email from Gmail addresses/ips would be actually spam.
I urge everyone to start using their own mail servers so the ecosystem around self hosting emails becomes super smooth.
why do receivers still rely on ip addresses when we have dkim and spf?
Lists are like the DRM kind of tech, where the genuine user has the real headaches (pay a service to filter my mail, cant self host etc) while the spams are still flowing through.
It is easy to get an email server running initially, but hard to get all the auxiliaries (SPF, DKIM, DMARC, MTA-STS, TLSRPT, BIMI, etc) set up correctly. It's even harder to debug deliverability issues, since there is 0 feedback on why your email is not being delivered. To a point where it inspired me to build an email hardening monitoring/validation service [0].
At the risk of being downvoted by people who are frustrated by email deliverability (and it is frustrating, I know): when you have email deliverability issues, it is almost always because you did something wrong on your end. Remember that false positives in spam detection hurts the $EVIL_BIG_CORP receiver as much as it does to you as a sender.
However, when I set up my first email server most emails were delivered just fine, however emails to a Microsoft domain (hotmail, outlook, etc) all were marked as Spam.
Then I switched to a new IP and since then everything has been great.