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Re:Show HN: OpenBSD Email Service – A free-email alternative by snksnk on Friday February 16, 2018 @03:21PM (#16395744)
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.
Re:Show HN: OpenBSD Email Service – A free-email alternative by sfilargi on Friday February 16, 2018 @03:44PM (#16395988)
I have DKIM, SPF, etc. but still gets caught by spam. What do you mean by "trusted host"?
Re:Show HN: OpenBSD Email Service – A free-email alternative by snksnk on Friday February 16, 2018 @03:58PM (#16396155)
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>
Re:Show HN: OpenBSD Email Service – A free-email alternative by sfilargi on Friday February 16, 2018 @04:02PM (#16396214)
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.

Re:Show HN: OpenBSD Email Service – A free-email alternative by tux1968 on Saturday February 17, 2018 @01:46AM (#16399419)
You're transiting over their network anyway -- the jig is already up even without relaying via their gateway.
Re:Show HN: OpenBSD Email Service – A free-email alternative by justinclift on Saturday February 17, 2018 @03:16PM (#16402484)
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.

Re:Show HN: OpenBSD Email Service – A free-email alternative by phaer on Friday February 16, 2018 @05:26PM (#16397052)
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.