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Re:Ask HN: Self Hosted vs. Gmail / Outlook? by sliken on Thursday May 04, 2017 @04:13AM (#14263344)
I've heard this before, but I have my own vanity domain, a well run mail server (postfix), and I I've never had a problem. I do support DKIM, SPF, DNSSEC, and of course I don't send spam.

I have heard that newly registered domains do have a period before they are trusted.

Re:Ask HN: Self Hosted vs. Gmail / Outlook? by mister_unknown on Thursday May 04, 2017 @04:22AM (#14263393)
I can confirm that. It took me a while to get a sane mailserver setup, but eventually I don't have any troubles with Gmail/MS/Yahoo anymore.
Re:Ask HN: Self Hosted vs. Gmail / Outlook? by atmosx on Thursday May 04, 2017 @08:24AM (#14264263)
I used to run my own mail server for ~7 years and never had issues. I used DKIM, SPF, etc and still do although they're problematic with mailing lists...

Postfix before, openSMTPd the last few years.