Question

Website email arrives at Gmail and other domains but not Hotmail.com or Outlook.com

I have a domain for example https://example.com website setup on a DO VPS. I have configured the VPS to be the primary MX for the domain and configure what I believe is an appropriate SPF record for it. The VPS is running postfix and can send and receive email for the domain. I can receive email fine to multiple other domains.

I also note that a similar question has been asked before but the work-a-round was performed by the person adding the email address to the safe senders list using outlook.com web interface. This is unsuitable for my purposes because the emails need to arrive at outlook.com or hotmail.com mailboxes without intervening.

Has anyone got any information that could allow me to get to the bottom of why hotmail / outlook.com aggressively blocks valid email while hiding behind many pages of policy documents that don’t enlighten me as to why I have an IP address designated as “Not qualified for mitigation”.

I have attempted to engage with Microsoft regarding how to go about getting it working but if anyone has any experience with getting a Droplet to email directly to mx*.hotmail.com MX servers and have the email accepted I would love to hear from you.

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I found this in the microsoft support forum. The page looks very similar to the sender.office.com page linked above, but requests many more fields. Perhaps this is the updated version of the same service. https://support.microsoft.com/en-us/getsupport?oaspworkflow=start_1.0.0.0&wfname=capsub&productkey=edfsmsbl3&locale=en-us&ccsid=635639051175184163

I’ve been fighting to get Hotmail to accept our emails for a long time. We go through this process with pretty much every new website or IP address. We have a brand new IP address and server from DigitalOcean, but apparently Microsoft doesn’t really give you anyway to reset the history of an IP address. But you might as well try these things:

Just keep on repeating those steps every few weeks. Good luck.

I’m having a hard time as well. New emails are not bounced, nor do I get an error message in my mail log. Funny thing is, replying to an email sent from a hotmail account DOES work. So I had a look at the differences in headers. The only field was:

in-reply-to: <AMSPR05MB1163A06679EE051280F0EF78EE20@AMSPR05MB116.eurprd05.prod.outlook.com>

This resulted in the following DMARC report:

<policy_published>
<domain>engeen.nl</domain>
<adkim>r</adkim>
<aspf>r</aspf>
<p>none</p>
<sp>none</sp>
<pct>100</pct>
</policy_published>
<record>
<row>
<source_ip>188.166.43.30</source_ip>
<count>3</count>
<policy_evaluated>
<disposition>none</disposition>
<dkim>pass</dkim>
<spf>pass</spf>
</policy_evaluated>
</row>
<identifiers>
<header_from>engeen.nl</header_from>
</identifiers>
<auth_results>
<spf>
<domain>engeen.nl</domain>
<result>pass</result>
</spf>
<dkim>
<domain>engeen.nl</domain>
<result>pass</result>
</dkim>
</auth_results>
</record>

I have no idea what do try next… Does anyone know of an affordable relay as an alternative?