Help me set reasonable expectations re: E-mail on DirectAdmin

NTT

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Nov 28, 2020
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I ran my own mail server for a decade in a half. At the end I was running Zimbra, had everything configured cleanly, and randomly Microsoft, Gmail, or others would start routing legitimate e-mail into their Spam folders. Since this was affecting clients I surrendered and now pay the Microsoft Tax on o365. I figure this is part of dealing with an oligopolistic market.

Now I'm offering hosting again, and comments here suggest e-mail works, so I'm trying, but I'm getting routed to SPAM.

So far I think I've done everything right: according to tests by allaboutspam.com, mxtoolbox, and a DNSBL lookup:
  • Reverse DNS is set correctly
  • Server HELO is good (even though EXIM isn't connecting as mail. - it's hostname.)
  • I'm not on any blocklists
  • SPF is working, and says my server is authorized to send for me
  • DKIM is working
  • There's no content that looks like spam in the URIBL, and spamassassin isn't flagging it
  • DMARC is published and enabled
I see green lights everywhere, and yet ticket notifications and outgoing tests I send are all routed straight to the junk folder of my main (o365) mail account.

Should I just accept this, and offer e-mail through a third party for those who need it? Or might there be another trick I need to use, like telling EXIM to identify itself as mail.mydomain.tld instead of realhostname.mydomain.tld?
 
No I have all the same stuff setup and my emails don’t get sent to spam.

Is this a brand new server and ip?
 
contact microsoft and and ask for mitigation for your ip
had same situation with some servers and contact with ms helped
As @bdacus01 mentioned is this an new ip ?
 
This is a new IP actually, so no traffic has been seen from this before.

I'll reach out to Microsoft and see if that resolves the issue.
 
This is a new IP actually, so no traffic has been seen from this before.

I'll reach out to Microsoft and see if that resolves the issue.
This might help to.
 
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