Outlook.com incorrectly marking emails sent from my server as SPAM

Brief issue description:

Whenever a user sends an email from my custom domain and server to an @outlook.com email address, the email is classified as spam.

Quick information:

  • My email server is hosted on a VPS and has been on it for the past ~7 weeks.
  • There were deliverability issues with Outlook. Phoned them. Fixed it.
  • IP address was part of a blacklist (Rats Dyna). Contacted list maintainers. Sorted it out.
  • DNS records are set. Reverse DNS. SPF. DKIM.
  • No mass emailing (bulk emailing). Only "normal" email usage
  • Sending emails via Mozilla Thunderbird.
  • Mail-Tester.com 10/10, IsNotSpam.com pass

I will be glad to provide any additional details and would be very grateful if a Microsoft representative could help me solve this issue.

Thank you very much.

Any help?

Thanks

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Only the deliverability folks can mitigate your issue.  This is a peer to peer site staffed mostly by volunteers who have little or no contact to MS.  Suggest you fill out one of the below forms


https://support.microsoft.com/en-us/getsupport?oaspworkflow=start_1.0.0.0&wfname=capsub&productkey=edfsmsbl3&locale=en-us&ccsid=635612678637576127&wa=wsignin1.0

or here

Cat herder
Windows Insider MVP
MVP-Windows and Devices for IT
http://www.zigzag3143.com/

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Only the deliverability folks can mitigate your issue.  This is a peer to peer site staffed mostly by volunteers who have little or no contact to MS.  Suggest you fill out one of the below forms


https://support.microsoft.com/en-us/getsupport?oaspworkflow=start_1.0.0.0&wfname=capsub&productkey=edfsmsbl3&locale=en-us&ccsid=635612678637576127&wa=wsignin1.0

or here

I was trying not to use that form because AFAIK that is for deliverability issues such as email bouncing back, which I had in the past and got it sorted out, and not for reporting issues within their SPAM classifying algorithm.

However, I just submitted a form with all these details. I'll let you know if it gets sorted out.

Thanks!

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Wish I could do more but those are the only folks who can mitigate this issue.  Good Luck
Cat herder
Windows Insider MVP
MVP-Windows and Devices for IT
http://www.zigzag3143.com/

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Apparently they refused my request.

Our investigation has determined that the above IP(s) do not qualify for mitigation.

I have just sent an email asking for clarification.

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That was far faster than I have ever seen.  Perhaps it is an issue with your host.
Cat herder
Windows Insider MVP
MVP-Windows and Devices for IT
http://www.zigzag3143.com/

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That was far faster than I have ever seen.  Perhaps it is an issue with your host.

Okay, so they got back to me with a generic response. What bothers me so much is that they keep on telling me to better manage my newsletters despite not having sent a single one. This is an obvious issue: my subnet was used for spamming. RatsDyna says so, and Hotmail completely blocked emails from my VPS from the beginning.

However, this is an issue that I haven't had anything to do with in the first place, because this problem existed even before I purchased my server.

This is the email that I got in response:

We have reviewed your IP(s) (xxx.xxx.xxx.xxx) and determined that messages are being filtered (i.e. sent to the Junk folder) based on the recommendations of the SmartScreen® Filter.

Email filtering is based on many factors, but primarily it's due to mail content and recipient interaction with that mail.  Because of the proprietary nature of SmartScreen® and because SmartScreen® Filter technology is always adapting and learning more about what is and isn't unwanted mail, it is not possible for us to offer specific advice about improving your mail content. However, in general SmartScreen® Filter evaluates specific words or characteristics from each e-mail message and weights them, based on their likelihood to indicate that a message is unwanted or legitimate mail. 

Unfortunately, after reviewing the information you provided and in compliance with our mail policies, we are unable to offer immediate mitigation for your deliverability issue. However, we have some specific recommendations for you to consider that can help you to improve deliverability over time.

Here are some specific recommendations for you to consider:

Brand your mail
Ensure mails are cleanly formatted and clearly identifiable as originating from your service.

Follow content and formatting best practices
There are numerous Internet resources which offer advice and best practices, we recommend you refer to these resources for assistance creating well formatted and more deliverable email.

Highlight Opt In

Clearly mark your emails so that Windows Live Outlook.com customers are able to identify that they requested or subscribed to emails from your service.

Ensure your email lists are up to date
Remove those who do not want to receive the emails and consider making the unsubscribe process more visible to ensure you are only delivering mail to interested recipients.

Join the Junk Mail Reporting Program (JMRP)
We believe that your recipients are the best indicator that the email you are sending is wanted.  The JMRP program allows you to see which of your emails Outlook.com users have marked as junk or unwanted mail.  Reviewing the results in JMRP will provide to the most direct information on what characteristics of your email, customers, and ultimately SmartScreen®, consider to be unwanted. This helpful feedback mechanism allows you to ensure that mails being sent from your IP are not resulting in negative feedback that could impact your sending reputation. Being vigilant about users who mark your e-mail as unwanted or the types of messages that are being marked as unwanted can help you keep mailing lists updated with only interested users and modify future campaigns. In addition, monitoring user complaints can help you identify unintended mail traffic or detect a potentially compromised account sending unwanted mail to your customers. Enroll at
https://postmaster.live.com/snds/JMRP.aspx?wa=wsignin1.0.

Join the Smart Network Data Services program (SNDS)

The SNDS program provides data about traffic seen originating from your registered IP, such as mail volume and complaint rates. The data is built from the log files of the inbound mail machines and other servers at Outlook.com and Microsoft and represents factual information about the traffic from your mail servers to Outlook.com users. For more information about this free program refer to https://postmaster.live.com/snds/FAQ.aspx. To register, please go to http://postmaster.msn.com/snds/. (Tip: As part of the enrollment process, you are asked to sign the JMRP program agreement and then send a response to Support indicating that it has been signed.  It's not uncommon for that step in the enrollment process to be missed.)

We encourage you to take an active role in managing your email practices and infrastructure. The SmartScreen® filter is not static and it is possible to improve deliverability over time.  Implementing and maintaining email best practices such as those described above can help.

We also encourage you to download and apply the industry best practices found in our Outlook.com Enhanced Deliverabilitywhite paper.

Sincerely,

yyyyyyyyy

Outlook.com Deliverability Support Team

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I am facing same issue and got sent the same canned message even though i haven't sent a single promotional newsletter but casual business emails to coworkers.

If by some miracle op or someone else who has been in similar situation is reading this can you please tell me if you were able to resolve your problem?

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I am facing same issue and got sent the same canned message even though i haven't sent a single promotional newsletter but casual business emails to coworkers.

If by some miracle op or someone else who has been in similar situation is reading this can you please tell me if you were able to resolve your problem?

Hello, there's nothing I hate more than finding an old thread where OP describes the very same problem and not being able to get a reply from them. That is why I came back to give you an answer asap.

Chances are that the IP address of your server has been part of a spam network. Basically there's not much you can do other than start building up a good reputation. I've had the very same issue with Google and it works pretty much the same way.

However, there are a couple technical tweaks you can try like setting up DMARC and SPF that help make your emails more trustworthy. Don't send out any newsletter or unwanted emails from your domain, try using services like MailChimp for that if strictly necessary.

Try asking your recipients to mark your emails as NOT SPAM. That helps a lot. You should be seeing your emails arrive like they should but it could take a while. In the short term, remember to call your recipients and making sure they've seen your email.

Also, avoid spammy features like certain words, formats, outbound links, etc. And check if you're part of a blacklist: https://mxtoolbox.com/blacklists.aspx

It's gonna take a while, don't expect a quick fix for that. Been there, done that, finally succeeded.

Good luck with that.

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Last updated November 1, 2023 Views 3,189 Applies to: