Email spam folder problems with Outlook / Hotmail

I am having one hell of a time getting email set up. This is my first time setting up a discord server. My hosting service is Digital Ocean and I’m attempting to use mailgun as my email provider. Almost everything is working properly. I’m able to authenticate and send out emails, no problem. The problem is they are ending up in the spam folder of whomever they are sent. I have SPF record set up correctly according to MailGun, DKIM is set up correctly according to MailGun. I even have a dmarc record. PTR is configured correctly, reverse lookup resolves correctly. I’m at a loss. I’m out of free mailtester tries. Any ideas?

Have you looked at the mail header of a junkmailed message?

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I’ve looked through the mail header yes. I am either missing it, or don’t understand all of what I am seeing. It looks fine to me, then gets confusing toward the bottom. Here is the header of one of the test emails sent from my discourse server.

Edit: I deleted the header
@staff could you please delete the edit history? Thx.

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They are delivered to gmail inboxes, with no problem.

I have a feeling the problem may have to do with either or both the domain name / TLD

psilocybin - Illegal Schedule 1
.tk - commonly used by known problem domains

As you are using mailgun, do the emails fare well with the Email Spam Checker - Mailgun ?

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Yes, and they are being delivered to every other email provider I’ve tried, gmail, Comcast, etc, just not outlook servers. I did find my ip on an email blacklist due to misconfiguration, but am having difficulty getting the unlock key, even though the problem has been resolved. Seems like it’s only outlook/hotmail junking these. I’m waiting for support from mailgun.

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I finally got the unlock key. I had to change my ptr entry to the mailgun subdomain, then the emaili with the unlock key arrived. It’s going to be .org when it goes live so the .tk I’m using for staging will go away, maybe that will help. Still gets junked by outlook, but there is a message from discourse to check your spam folder so at this point, everything else is working and I don’t care lol. It’s a forum for discussing legalization, potential for treating depression, cluster headaches, etc, so since we aren’t selling anhything and highly discouraging any illegal activity, I’m not personally concerned with the schedule 1 status of a word in the domain name. If microsoft want’s to be ignorant/overly cautious like that, fine by me I guess. Thanks for the help and suggestions. Much appreciated! I can be a little bit of a perfectionist, but I’m going to have to let this go for now lol.

Did you test with as specified in the docs?


Yes, the only thing that came back was the missing dmarc entry, and ptr issue, both of which I fixed, but I ran out of free tests for the day.

Dmarc and ptr are CRITICAL, if you did not have those in place for weeks already you are starting from a very deep hole you need to dig yourself out of.


I’ve only been working on this for 2 days. The email I set up today.
Edit: Well, if you count screwing around with the dev server, 4 days total, but that shouldn’t matter.

Thanks for your help everyone. Great community here!

1 Like is gold, I recently sent them a fair bit of cash donation from Discourse to thank them for producing and maintaining that excellent resource.


I just ran another test today on and everything came back green, except the message format section suggested improvements. It was the standard discourse test email from the admin panel though.

I have no problem giving them money, it’s just I’m broke until tomorrow. =)

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