Single user unable to auto-forward/auto-redirect to external address

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This topic contains 3 replies, has 3 voices, and was last updated by Avatar hemanthkumar 7 months ago.

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    We have a single user (me) that is unable to use Outlook 2016 rules to automatically forward or redirect mails outside of the company. I can auto-forward and auto-redirect email internally.

    We have only one remote domain set up and it allows automatic fowarding. I have no transport rules in place to stop it from happening for me. We did set up some transport rules to prevent auto-forwarding and auto-redirect for specific groups of users but I’m not a member of any of those. I deleted and recreated my rules in Outlook. I deleted and recreated my Outlook profile on the client workstation. I ran a repair installation on Outlook. I tried creating the rules in OWA. I ran a check against my mailbox for corruption – there was none. I also compared a get-mailbox | FL against a user that is able to auto-forward/auto-redirect and besides the obvious account differences they’re identical. I looked at my properties in ADSIedit and nothing jumps out at me. We have a spam filter in the DMZ that has message tracking but it doesn’t look like the email is even getting to that point. Sounds to me like it’s a server side thing, but I’m at a loss where to go from here troubleshooting this issue. Will welcome any thoughts or insights on where to look or how to fix.


    Can you tell us a bit more about the Exchange environment (version, on prem or cloud….)

    Have you tried creating a mail contact for the external address and forwarding to that?


    Running Exchange 2010 SP3 UR21 on prem. 2 CAS/HUB servers, 2 mailbox, 1 with all 3 roles, 3-node DAG.

    Yes, I tried creating a contact and it didn’t work either. However, if I create a Transport Rule in Exchange it does work (except for emails marked with high importance”.

    Did a little more testing and when I do a Get-MessageTrackingLog and try to send using Outlook rules I get:
    EventId Source Sender Recipients MessageSubject
    SEND SMTP Test

    When it’s sent using the transport rule I basically get:
    SEND SMTP Test


    Finally ended up burning a support ticket with Microsoft. Although they didn’t come up with the exact answer they did lead me to another Google search expedition where I found an obscure post here:

    Where the following comment was made that seems to explain why I was unable to trigger on the domain name in the SMTP address:

    “The problem is that purely internal email does not seem to be evaluated by the full smtp address, so your rule won’t work if the email has never left the server.”

    The workaround was to specify a word or phrase in the message header, which is:

    “X-MS-Exchange-Organization-AuthAS: Internal”

    Which will look for emails generated internally. Seems to work.

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