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Regarding email, I spent some tens of hours setting it up, including implementing DKIM, DMARC, SPF and getting my mail delivered to Gmail and O365. That was ove

by dvdkon 6y ago

Regarding email, I spent some tens of hours setting it up, including implementing DKIM, DMARC, SPF and getting my mail delivered to Gmail and O365. That was over a year ago and things mostly just work with the occasional upgrade or configuration change. You could also save a lot of time by going with a pre-packaged solution. I understand if you don't have time for that, but at least in my experience, self-hosting email isn't the impossible task it's sometimes made out to be.

petronio 6y ago
My experience has been similar. The most important thing that can't be easily resolved is if the server's IP is already on the blocklists, but other than that DKIM, DMARC, SPF, and reverse resolution together solves the ~~magical ritual~~ heuristics that make the big guys happy.
imwillofficial 6y ago
It is near impossible. I did all the same things, totally valid and secure setup, gmail would never deliver. YMMV.
- quesera 6y ago
  Two negatives: new domain names, and historically troublesome sending IP addresses. And of course SPF, DKIM, DMARC are all prerequisites. But if you can avoid the first two problems, hosting email yourself is rock-solid reliable and requires very little attention.
- alephu5 6y ago
  I've got the same problem. Using a Hetzner VPS and can't find my IP on any blacklists but it's all sent straight to spam...
Anthony-G 6y ago
People’s experience with deliverability of messages from self-hosted mail servers seems to be very hit-or-miss but I’m another one of the lucky ones. Rather than using Mail-in-a-box or something similar, I used a cautions step-by-step approach. About 5 years ago, I read the O’Reilly book, Postfix: The Definitive Guide that had been sitting in my book-shelf for years. I installed and configured Postfix as a sending-only mail server on a Hetzner VPS. I sent a few test emails to GMail accounts and a friend’s Office 365 and they both worked! I then gradually added extra layers of functionality (TLS, DKIM, SPF, DMARC). Once I was happy that I could successfully send emails, the next step was to receive email: I added MX records for my domain and opened port 25 on the firewall. I was able to use Mutt over SSH to read emails sent to my account. I later installed Dovecot (excellent documentation) and Squirrelmail (lacking in features but was easy to install). I don’t really use web-mail but I’ll probably install Roundcube at some stage and I plan to learn how to use Sieve for automatic filtering. I thought I’d have serious problems with spam and have to install anti-spam software and/or use black-lists but that hasn’t (yet) been an issue. Simply using Postfix default options along with grey-listing and not accepting messages from invalid (according to SPF records) sources blocks all spam. The only times I received spam was when I had accidentally disabled the grey-listing (the mail logs show I get hundreds of connection attempts with only a tenth of successful connections being genuine). The system actually works better than GMail in that I don’t miss messages that were wrongly flagged as Spam. Another benefit of self-hosting is that I can quickly and easily set up account-specific email addresses, e.g., <hackernews@example.com> – no need for <anthony+hackernews@example.com> I gradually started using it instead of GMail and it’s now my primary email account for important communication. In the four years of serious use, I haven’t had any problems (touch wood).
- ywei3410 6y ago
  Once you start using Sieve, you can also start doing more fine-grained filtering of mail to locations and archiving things which you care about with a couple of bash scripts and systemd timers/cron jobs.

by dvdkon 6y ago

petronio 6y ago

My experience has been similar. The most important thing that can't be easily resolved is if the server's IP is already on the blocklists, but other than that DKIM, DMARC, SPF, and reverse resolution together solves the ~~magical ritual~~ heuristics that make the big guys happy.

imwillofficial 6y ago

It is near impossible. I did all the same things, totally valid and secure setup, gmail would never deliver. YMMV.

quesera 6y ago
Two negatives: new domain names, and historically troublesome sending IP addresses. And of course SPF, DKIM, DMARC are all prerequisites. But if you can avoid the first two problems, hosting email yourself is rock-solid reliable and requires very little attention.
alephu5 6y ago
I've got the same problem. Using a Hetzner VPS and can't find my IP on any blacklists but it's all sent straight to spam...

Anthony-G 6y ago

People’s experience with deliverability of messages from self-hosted mail servers seems to be very hit-or-miss but I’m another one of the lucky ones. Rather than using Mail-in-a-box or something similar, I used a cautions step-by-step approach. About 5 years ago, I read the O’Reilly book, Postfix: The Definitive Guide that had been sitting in my book-shelf for years. I installed and configured Postfix as a sending-only mail server on a Hetzner VPS. I sent a few test emails to GMail accounts and a friend’s Office 365 and they both worked! I then gradually added extra layers of functionality (TLS, DKIM, SPF, DMARC). Once I was happy that I could successfully send emails, the next step was to receive email: I added MX records for my domain and opened port 25 on the firewall. I was able to use Mutt over SSH to read emails sent to my account. I later installed Dovecot (excellent documentation) and Squirrelmail (lacking in features but was easy to install). I don’t really use web-mail but I’ll probably install Roundcube at some stage and I plan to learn how to use Sieve for automatic filtering. I thought I’d have serious problems with spam and have to install anti-spam software and/or use black-lists but that hasn’t (yet) been an issue. Simply using Postfix default options along with grey-listing and not accepting messages from invalid (according to SPF records) sources blocks all spam. The only times I received spam was when I had accidentally disabled the grey-listing (the mail logs show I get hundreds of connection attempts with only a tenth of successful connections being genuine). The system actually works better than GMail in that I don’t miss messages that were wrongly flagged as Spam. Another benefit of self-hosting is that I can quickly and easily set up account-specific email addresses, e.g., <hackernews@example.com> – no need for <anthony+hackernews@example.com> I gradually started using it instead of GMail and it’s now my primary email account for important communication. In the four years of serious use, I haven’t had any problems (touch wood).

ywei3410 6y ago
Once you start using Sieve, you can also start doing more fine-grained filtering of mail to locations and archiving things which you care about with a couple of bash scripts and systemd timers/cron jobs.