Yeah, I do the same - I plugged in Postfix, Dovecot and SpamAssassin and haven't had to touch it other than occasionally confirming backup scripts and automatic security updates are working.

Does you email get marked as SPAM by gmail?

I do something similar, but when I send an email to a person for the first time, it always ends up in the spam folder by GMail.

Just relay it out via a trusted host, in addition to setting up DKIM, SPF, etc.; that solved all the problems for me. My email server is working excellent for many years now (OpenBSD, OpenSMTPD, dovecot) with Rainloop as web-based frontend.

I have DKIM, SPF, etc. but still gets caught by spam. What do you mean by "trusted host"?

An email provider that is not blacklisted and allows relay. I currently use my ISP for that.

Taken from my smtpd.conf:

  table secrets { mylogin = [email]@ziggo.nl:[pass] }
  accept tagged DKIM for any relay via tls+auth://[email protected]:587 auth <secrets>

Oh, I see, thanks!

It kind of defeats the purpose, since now the third-party will be able to read all my outgoing emails, and have control over them.

You're transiting over their network anyway -- the jig is already up even without relaying via their gateway.

Connecting directly to the remote (non-ISP) mailserver with TLS shouldn't reveal any message contents.

Relaying via the ISP's mail server though (even with TLS) seems like it would disclose the message contents.

Is DMARC included in your 'etc'? I think thats needed for gmail these days. If rdns, dkim, spf and dmarc are there, try checking your IPs reputation (senderscore) that could be it.

Thirded, only with qmail. I know mine is a tiny private server, but scaling up would only require more hardware and minimal increase in hours working on it. OTOH, I manage hosted mail solutions for three other domains, and those all require more time, because I'm supporting other people.

This used to work for me but lately, way too much spam. Looking to install rspamd but have not succeeded yet.

Same here. I have owned my domain and ran my email server for six years now. Investing a week worth of afternoons harls really paid off and i can do neat things like having infinite email addresses via a catch-all address.

By the way, give a look at mail-in-a-box, another cool project that implements a ready to use mail server with great functionalities.

Used to manage it all manually, set up https://mailcow.email/ after a server move a couple years ago. It's been great, running inside docker now via docker-compose alongside https://github.com/JrCs/docker-letsencrypt-nginx-proxy-compa... for automatic letsencrypt for the web interface along with my additional web services hosted on the same server. I had one minor hiccup when upgrading wherein I had to restart all docker containers, that's about it in terms of maintenance.

I did the same and used my catch-all extensively which I almost regret nowadays because it would make migration to a hosted service much more difficult if I ever wanted to. At least I know of no trustworthy commercial mail hoster which allows catch-all-addresses without requiring a much more expensive 'business' account.

I do this in fastmail with no issues. I'm on an older plan of around $40 a year I think but have zero regrets switching from gmail

For what it's worth, Zoho.com gives catch-all ability with their free tier as long as you supply your own domain.

Do you have the system updates on auto? How do you handle all of that?

On Debian and derivatives, you can install unattended-upgrades to get automatic security updates. See also apt-listchanges, which can send you an email detailing the changes applied.

Similar for RHEL/CentOS/other-EL based distributions too, using the "yum-cron" package.