Hotmail Silently Dropping Emails From Work Domain

We recently switched to a new domain and mail server, and since then we havent been able to deliver emails to hotmail.com @outlook.com addresses until a user sends us a message and we reply to them. Or they add us to their safe list.

Despite the fact that our IP is clean, we have valid SPF, DKIM and PTR set.

There is no bounced email so we have no idea of knowing which one of our email to the hotmail client is received, hotmail just silently drops the email.

Can one of the reps PM me so i can share my domain and other information.

Hello,

The issue might be with the server that needs to be checked or configured by your ISP. We suggest that you contact your internet or email service provider to better assist with your concern.

If you have further questions feel free to get back to us.

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My service provider and I have already checked the mail server, the SPF, DKIM, PTR passes. There's no data on JMRP and SNDS reports our IP as clean too.

AND i am able to send emails to everyone else but Hotmail.

Someone from Outlook Deliverability Support has replied to my emails with a canned message which isn't relevant to me. Still waiting for them to get back to me after my response. 

You're asking me to change my newsletter when i haven't sent a single one, Hotmail is sending messages from our domain to my and my client's hotmail emails to a void.

They claim it's being sent to Delete folder but i can't even find them there even after running the recorvered deleted emails fucntion.

Hello,

My name is Anirudh and I work with the Outlook.com Deliverability Support Team.

We have reviewed your IP XXXXXXXX and determined that messages are being filtered (i.e. sent to the Delete 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 Deliverability white paper. 

Sincerely,

Outlook.com Deliverability Support

 

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Hi,

I am having exactly the same problem.

I run two domains, one for my business and a family one which my wife uses for a local club and in the last month or so we have failed to get messages to any of the hotmail, outlook or live addresses.

We run our own mail server and have a fixed IP and have done so for several years, but then in early May we started getting issues sending to the MS addresses.

I think that it is down to the fact that our ISP changed our fixed IP address in early May, but can't get a straight answer from the Outlook.com Deliverability Support Team.

The Outlook.com Deliverability Support Team are worse than useless completely ignoring the information being provided in the initial support requests and then ignoring the responses to the canned messages they keep on sending back to you.

We have been through the support teams recommendations as well as made a number of other improvements, but none of them seem to make the slightest difference.

Since is it the MS SmartScreen® Filter tech that is blocking our legitimate emails we are ending up getting customers to move over to GMail so they can actually receive the emails they are expecting.

If anyone out there could help it would be appreciated.

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Hi,

I have the same problem, and randomly not for all email accounts.

I'm able to send emails to Hotmail, yet one of my colleges was not, and we are both under the same domain !! 

When I added the Email contact and saved it in the addressbook - without a need to make it white list - I was able to receive normally..

I have some questions: 

  • Why does Hotmail drop without a delivery failure message to the sender??????
  • What is the use of the Junk folder in such cases?
  • How can we fix this issue?

We can't contact all our customers who use Hotmail to ask them if they receive our email !!!

Thanks,

Khalid.

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Hello Khalid,

We understand that you're having some issues with your email account. Regarding your questions, we may need to verify some details first for us to determine the appropriate advice. To answer your first question, it is actually depends on the type of account that you have. It could be a server issue or with the settings in your email account. For your second question, Junk folder is where the spam messages are being stored. For your last question, since we still need some details first, kindly provide us the information to the following:

  • What is the domain of your email account?
  • Do you use an email application to access your account, or do you access it through a web browser?
  • If you're using an email application, what application is it?
  • Is your account a personal or an organization/company provided email account? Is it a business type of email account?
  • What troubleshooting steps have your tried so far?

Looking forward to your response.

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And I am having the same problems as Genyus and Khalid. 

In the longer version of the email from Outlook Deliverability Support it says:

 (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.)

Does anyone know where/how to do this "send a response"? I have tried several links, but they seem to send me in a circular loop back to the bot-response emails.

Again, as with your clients above, I have proper SPF, DKIM, DMARC, reverse PTR, all verifies by mxtoolbox. Emails to all other tested sites go through properly.

Can anyone from Microsoft help me (or all of us) get this sorted?

I have seen on the web that people have overcome this problem by appealing directly to Directors and VP's at Microsoft. Surely we shouldn't have to do that.

Pat Beirne

patb (at) apphost.ca

Pat Beirne
CTO AppHostCanada

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Hello Pat,

We understand that you're also having the same issue as the others. For us to better assist you, please provide us the answers to the following questions that we provided in our above response to Khalid Rehan, on this thread.

Looking forward to your response.

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Thank you for responding.

  • What is the domain of your email account?
    • csdlabs.com
    • apphostcanada.com
  • Do you use an email application to access your account, or do you access it through a web browser?
    • my clients are the senders of email; they send emails through various clients, all of which are routed through our PostFix SMTP sender
    • this PostFix has DKIM header capabilities
    • we have no control over how the recipients of our emails read them
  • If you're using an email application, what application is it?
    • our clients use K9, Thuderbird, Roundcube, GMail and various other IMAP clients
    • all these resolve to our PostFix 2.11 server which sends to Outlook/Hotmail/Live
  • Is your account a personal or an organization/company provided email account? Is it a business type of email account?
    • this is a corporate email system
  • What troubleshooting steps have your tried so far?
    • we have moved to complete compliance with the requirements posted at postmaster.live.com
    • SPF has been implemented since 2014. DKIM and DMARC were implemented a few days ago; verified at mxtoolbox & accepted by gmail & yahoo and others
    • reverse pointers are implemented, MX record is clean
    • we block relays
    • we have never sent marketing newsletters, or any other email which would require an "unsubscribe"
    • joined JMRP and SNDS

Lawrence, from your listed questions, you seem to think this is a recipient user problem. The problem isn't there, it's with Microsoft's silly SmartScreen system blocking business emails. Just like Mr. Voelcker and Mr. Genyus and Mr. Khalid. So the question restated is:

As sysadmins, what to we have to do in order to get our corporate emails through to our clients who are using @outlook.com or @hotmail.com accounts? [given that we've already gone through the requirements listed at postmaster.live.com]

Pat Beirne
CTO AppHostCanada

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And to be perfectly clear, the problem is that our clients are having trouble sending emails to their collegues who have @outlook.com/@hotmail.com. These emails end up in the Junk folder and get missed.

Our clients are trying to make appointments and establish relationships with business professionals, and having our emails end up in Junk leaves a terrible impression, never mind the missed opportunities, bad faith and loss of business. 

Secondly, in the longer version of the email from Outlook Deliverability Support it says:

 (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.)

Could you please inform all of us on this list how we are supposed to "send a response to Support"?

Pat Beirne

Pat Beirne
CTO AppHostCanada

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This frustrating problem has been around for awhile. My ISP worked on it and gave up. I run a small business and clients with a Hotmail address frequently don't get my correspondence and they think I'm unresponsive. It just happened again and that's how I stumbled on this thread. It's absolutely inexcusable that the messages fail silently.

Here is a blog post from 2015 that explains it.

https://blog.paranoidpenguin.net/2015/01/outlook-com-is-silently-discarding-email-messages/

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Last updated February 23, 2021 Views 1,431 Applies to: