Postfix mail server not delivering to hotmail.

Posted March 6, 2017 12.2k views
EmailUbuntu 16.04

I have a server that I’m using to send mail via postfix. It’s delivering to other major providers like gmail and icloud, but it’s not sending to any of microsoft’s domains.

A bit of background, I initially didn’t realise I needed to do anymore work after installing postfix, so I was sending messages without any authentication, after a couple of days they stopped reaching my personal hotmail account.

I’ve since sorted out the SPF, DKIM, DMARC and PTR records so that it’s a much more legit operation, but alas, nothing is reaching my hotmail account.

If you need more information to diagnose the problem, please let me know and I’ll provide.

1 comment
  • I am also having the same issue. Anybody with microsoft exchange server cannot email us. If we also email hotmail it bounces back to us. What is the problem? All other mail is fine. This has only started happening, we had no problems before.

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6 answers


One of the first things I’d recommend would be a scan on your IP and Domain against blacklists. This will let you know if blacklists are the issue.

Hotmail is pretty picky about how fast you send transactions. As @hansen said, the mail log should give you the reason that mail cannot be delivered and from there we could provide some help in addressing the problem.

The same is happening to me.

My startup’s email server is hosted on DigitalOcean. For an unknown reason it does not deliver emails to any of Microsoft’s services (Hotmail, Live, Outlook).

I’ve been running it for two years, it only sends legit personal emails, not even “drip campaigns” or such.

Their mx reports that the mail has been delivered, but it does not appear in the recipient’s inbox or spam folder. It is simply lost and I can’t even monitor delivery errors. Sometimes a message goes through (usually a direct reply to an incoming mail) but that’s not even guaranteed. There are no errors in postfix. The message is reported as delivered.

I’ve completed all checklists, my mailserver uses DKIM, SPF, in-transit TLS, does not send spam, has a reverse PTR, etc, etc. The IP is not listed in any blacklist. I get a perfect 10/10 score in most mail tester services.

Other MXs like Gmail and Yahoo! deliver emails properly, sometimes to the spam folder but that is usually fixed when the recipient clicks on “Not spam”.

Contacting their support is talking to a wall. It’s impossible to get a non-canned response.
Short of paying the extortion fee for a “deliverability certificate” I honestly don’t know what else to do. I understand spam is a serious issue but come on, how are small businesses supposed to send emails if they don’t want a third party like Google Apps to read them?

  • hello did you find out how to resolve this issue? iam having the same issue

    • Three years later… unfortunately it isn’t fixed.

      Or, I would say, sometimes it works, but there is no guarantee.

      The bottom line is: don’t set up a mail server on a VPS (or at home, for that matter). It’s sad, but that’s the current status of mailservers.

I have exactly the same issue with my new application. No problems sending to emails in yahoo or gmail but emails just does not reach hotmail accounts.

/var/log/maillog says emails are queue for delivery by postfix/smtp and removed by postfix/qmgr.