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

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:

• JMRP and SNDS: Sign up to get hotmail spam reports https://postmaster.live.com/snds/addnetwork.aspx
• https://support.microsoft.com/en-us/getsupport?oaspworkflow=start_1.0.0.0&wfname=capsub&productkey=edfsmsbl3&ccsid=635688189955348624&wa=wsignin1 - They’ll always just tell you your IP is “not qualified for mitigation”. Just keep on replying to their emails and ask them to do something to help you. If nothing happens, fill out the form again every couple of weeks and try again.
• Email delist@messaging.microsoft.com
• Fill out the form at https://sender.office.com
• Try calling Microsoft at 800-865-9408. I didn’t have any luck with that, but some people say they have.
• Post multiple messages in https://answers.microsoft.com/en-us/outlook_com/forum?tab=Threads. Some Microsoft employees do sometimes read those messages and every now and then you’ll get someone who can help. But you have to be persistent and continue posting new threads every few days.
• Ask people who use your website not to use @outlook.com or @hotmail.com email addresses and tell them why.
• Send an email from a Hotmail account to your blocked email address. And also reply from your blocked email address. You should at least get the reply. Check it in Hotmail (view source) for any issues that appear in the headers.

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?