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Outlook 2016 not showing NS delegated domains correctly as 'From' RRS feed

  • Question

  • So here's the problem. I work on an invoicing software package that sends mails in name of their customers. Customers need to set up their DNS to include a NS record, which delegates a subdomain to us. This allows us to control SPF/DKIM keys, so our customers don't need to be too techsavvy to get this going. Furthermore it allows us to send mails with correct keys in name of our customers, so the mails do not come in spamboxes.

    So a large overview of the flow would be:

    "Customer Domain" <---- Subdomain delegated to ----> "Invoicing Mailing Software" <---- Sending mail to ----> "Customer of our customer with 'from:' set to our customer's domain"

    This works great; thousands of mails are send in name of our customer from our mailing provider. There is a problem however when a customer of our customer is using Outlook 2016: the subdomain is shown, instead of the customer domain as the 'from'. It seems that Outlook 2016 is using the wrong header to determine it's from field, namely the 'sender' email header, instead of the 'from' email header. Surprisingly enough, the webclient of Outlook is NOT affected by this and correctly shows the value of the from header in the from field in the interface, instead of the sender header in the from field, what the Desktop client is doing.

    The headers that are send with the mail are as following (changed the domains for privacy reasons):

    From: "Testdomain" info at testdomain dot com Reply-To: "Testdomain" info at testdomain dot come Return-Path: info at 123847thgashfjhjykf-invoicingcompany dot testdomain dot com Sender: info at 123847thgashfjhjykf-invoicingcompany dot testdomain dot com

    TL;DR:

    Outlook is showing "info at 123847thgashfjhjykf-invoicingcompany dot testdomain dot com" in the from field, instead of "info at testdomain dot com".

    We contacted Microsoft through phone and mail previously, and they seem to insist on changing our SMTP servers, but that is not the problem, since we can replicate this issue, by just importing an EML with these headers and the problem persists. It does not matter which mailprovider the receiver is using, it happens on all of them; POP3/IMAP/Exchange, it all doesn't matter. That's why we highly suspect that Outlook 2016 has a bug in which header it should use for the from field.

    Maybe other outlook versions are affected as well, but that is not known at the moment.

    Please help so that the correct domain is shown in Outlook 2016.


    Thursday, October 3, 2019 10:45 AM

All replies

  • Hi Robbin,

    >> So here's the problem. I work on an invoicing software package that sends mails in name of their customers. Customers need to set up their DNS to include a NS record, which delegates a subdomain to us. This allows us to control SPF/DKIM keys, so our customers don't need to be too techsavvy to get this going. Furthermore it allows us to send mails with correct keys in name of our customers, so the mails do not come in spamboxes.

    We may not be familiar with your settings and cannot test your issue in our environment. And it seems the issue is related to your settings

    >> Surprisingly enough, the webclient of Outlook is NOT affected by this and correctly shows the value of the from header in the from field in the interface,

    Please try testing as below:

    1. Sending and recieving emails on the web mail.
    2. Send with Outlook 2016 client and check the email header on the web mail.
    3. Send on the web mail and check the email header in the Outlook 2016 client.


    Besides, please make sure you have upgraded your Outlook client to the latest version. It is alos suggested to configure your accounts on another computer(Outlook) or other versions of Outlook and see if there is any difference.

    Any update, please feel free to post back.

    Regards,

    Aidan Wang


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.

    Friday, October 4, 2019 8:07 AM
  • Hi Robbin,

    Have you got the issue fixed?

    Please try my suggestions and let me know the results.

    Regards,

    Aidan Wang


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.

    Monday, October 7, 2019 9:25 AM
  • Hey there! We have tried the different issues.

    We mailheaders seem to be the same in all clients (which is expected of course). None of the other clients we tried had this problem (Roundcube webmail, Mailcatcher, gmail, Outlook Web, Thunderbird, Apple Mail and the default mail client of windows 10). Outlook 2016 still seems to be using the 'sender' mail header in the 'from' field.

    Outlook is updated. We have tried different account, all with the same result. (Microsoft account, gmail account and some other IMAP, as well as just loading the EML file without account).

    I can send a testmail if you want, so you can test it in your environment, since it seems to be environment independent and just plain straight a bug in outlook 2016.

    Just to be clear: it is the _receiver_ that is having the problem! It is entirely independent of the sender!!


    • Edited by Robbin_003 Friday, October 11, 2019 10:46 AM
    Friday, October 11, 2019 10:45 AM
  • Hi Robbin,

    Do you mean that all Outlook 2016 clients in your organization are having this problem? If so, this issue may be related to the conflict between your environment settings and Outlook client.

    If it is  just one computer(Outlook 2016 client) is having this problem, then the issue may be caused by this specific Outlook 2016 client. It is suggested to repair your Office installation. Or just uninstall and re-install your Office.

    Regards,

    Aidan Wang


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.

    Monday, October 14, 2019 8:50 AM
  • No, I mean that all outlook 2016 instances are having this problem.Not just in our environment, but every client that is receiving mail from us.

    I don't have the idea that you understand the scope of the problem. To put it simply:
    Outlook shows the 'sender' header in the 'from' field.
    Sender header bad, from header good for that field.

    While the sender and from headers are usually the same, they are not always the same; that's the assumption that Outlook 2016 Desktop plain straight is wrong about and I consider it a bug.

    Monday, October 14, 2019 11:27 AM
  • Hi Robbin,

    Thanks for your reply.

    I haven't found any official article about this issue, so it is suggested to pay attention to the next update of Outlook, once there is new update, just install it and see if the issue will go.

    If the issue continues, it is encouraged to share your feedback via the Outlook UserVoice forum.

    Regards,

    Aidan Wang


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.

    Thursday, October 17, 2019 8:08 AM
  • Hi,

    I'm writing to see if the reply above is helpful to you. If yes, would you mind helping mark the reply as answer? So that others who might have a similar question can benefit from your thread? Thanks for your understanding and support.

    Regards, 

    Aidan Wang


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.



    Monday, October 28, 2019 9:03 AM