# Email spam folder problems with Outlook / Hotmail
**URL:** https://meta.discourse.org/t/email-spam-folder-problems-with-outlook-hotmail/93425
**Category:** Self-hosting
**Created:** [July 29, 2018, 10:56pm UTC](https://meta.discourse.org/t/email-spam-folder-problems-with-outlook-hotmail/93425 "2018-07-29T22:56:34Z")
**Posts on this page:** 15
**Page:** 1
### Author:  [@visions710](https://meta.discourse.org/u/visions710)
#### Post date: [July 29, 2018, 10:56pm UTC](https://meta.discourse.org/t/email-spam-folder-problems-with-outlook-hotmail/93425/1 "2018-07-29T22:56:34Z")
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?
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### Author:  [@Stephen](https://meta.discourse.org/u/Stephen)
#### Post date: [July 29, 2018, 11:50pm UTC](https://meta.discourse.org/t/email-spam-folder-problems-with-outlook-hotmail/93425/2 "2018-07-29T23:50:19Z")
Have you looked at the mail header of a junkmailed message?
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### Author:  [@visions710](https://meta.discourse.org/u/visions710)
#### Post date: [July 30, 2018, 12:23am UTC](https://meta.discourse.org/t/email-spam-folder-problems-with-outlook-hotmail/93425/3 "2018-07-30T00:23:59Z")
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](https://meta.discourse.org/groups/staff) could you please delete the edit history? Thx.
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### Author:  [@visions710](https://meta.discourse.org/u/visions710)
#### Post date: [July 30, 2018, 12:27am UTC](https://meta.discourse.org/t/email-spam-folder-problems-with-outlook-hotmail/93425/4 "2018-07-30T00:27:11Z")
They are delivered to gmail inboxes, with no problem.
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### Author:  [@Mittineague](https://meta.discourse.org/u/Mittineague)
#### Post date: [July 30, 2018, 1:19am UTC](https://meta.discourse.org/t/email-spam-folder-problems-with-outlook-hotmail/93425/5 "2018-07-30T01:19:18Z")
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: Send Spam Test Emails - Transactional Email API Service For Developers | Mailgun](https://www.mailgun.com/deliverability/email-spam-checker) ?
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### Author:  [@visions710](https://meta.discourse.org/u/visions710)
#### Post date: [July 30, 2018, 1:32am UTC](https://meta.discourse.org/t/email-spam-folder-problems-with-outlook-hotmail/93425/6 "2018-07-30T01:32:48Z")
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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### Author:  [@visions710](https://meta.discourse.org/u/visions710)
#### Post date: [July 30, 2018, 2:35am UTC](https://meta.discourse.org/t/email-spam-folder-problems-with-outlook-hotmail/93425/7 "2018-07-30T02:35:49Z")
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.
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### Author:  [@codinghorror](https://meta.discourse.org/u/codinghorror)
#### Post date: [July 30, 2018, 2:41am UTC](https://meta.discourse.org/t/email-spam-folder-problems-with-outlook-hotmail/93425/8 "2018-07-30T02:41:10Z")
Did you test with [mail-tester.com](http://mail-tester.com) as specified in the docs?
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### Author:  [@visions710](https://meta.discourse.org/u/visions710)
#### Post date: [July 30, 2018, 2:45am UTC](https://meta.discourse.org/t/email-spam-folder-problems-with-outlook-hotmail/93425/9 "2018-07-30T02:45:06Z")
@codinghorror
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.
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### Author:  [@codinghorror](https://meta.discourse.org/u/codinghorror)
#### Post date: [July 30, 2018, 2:47am UTC](https://meta.discourse.org/t/email-spam-folder-problems-with-outlook-hotmail/93425/10 "2018-07-30T02:47:49Z")
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.
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### Author:  [@visions710](https://meta.discourse.org/u/visions710)
#### Post date: [July 30, 2018, 2:48am UTC](https://meta.discourse.org/t/email-spam-folder-problems-with-outlook-hotmail/93425/11 "2018-07-30T02:48:29Z")
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.
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### Author:  [@visions710](https://meta.discourse.org/u/visions710)
#### Post date: [July 30, 2018, 12:35pm UTC](https://meta.discourse.org/t/email-spam-folder-problems-with-outlook-hotmail/93425/12 "2018-07-30T12:35:24Z")
Thanks for your help everyone. Great community here!
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### Author:  [@codinghorror](https://meta.discourse.org/u/codinghorror)
#### Post date: [July 31, 2018, 12:20am UTC](https://meta.discourse.org/t/email-spam-folder-problems-with-outlook-hotmail/93425/13 "2018-07-31T00:20:27Z")
[mail-tester.com](http://mail-tester.com) is gold, I recently sent them a fair bit of cash donation from Discourse to thank them for producing and maintaining that excellent resource.
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### Author:  [@visions710](https://meta.discourse.org/u/visions710)
#### Post date: [July 31, 2018, 4:05am UTC](https://meta.discourse.org/t/email-spam-folder-problems-with-outlook-hotmail/93425/14 "2018-07-31T04:05:33Z")
@codinghorror
I just ran another test today on [mail-tester.com](http://mail-tester.com) 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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### Author:  [@system](https://meta.discourse.org/u/system)
#### Post date: [August 30, 2018, 4:05am UTC](https://meta.discourse.org/t/email-spam-folder-problems-with-outlook-hotmail/93425/15 "2018-08-30T04:05:34Z")
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