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Mail to Local Recipient Sent Externally

    Question

  • Hey. I have mail from a local exchange user -> another local exchange user being sent out through a Send Connector to another host. Protocol logs and Message tracking logs confirm this. It is only hapening for this user. There is no forwarding address set on the mailbox, nor is there an inbox rule to forward the mail. I bounced the Mailbox Transport Service to no avail. I added a new smtp address to the mailbox and explicitly addressed an internal mail to the new address but it still goes out the send connector. I am at a loss. Can anyone shed some light? Thanks.
    Thursday, September 14, 2017 2:08 PM

Answers

  • To close the thread, found the issue. The users in question had the targetAddress attribute set to SMTP:user@domain.org. Maybe they were converted from a contact/mail user at some point. I don't know why Exchange would choose to route it over the send connector when the address is local. One for the head scratcher.
    Monday, September 18, 2017 2:07 PM

All replies

  • Hi, 

    Is the recipient located on another site? If yes, the send connector can be used for delivery. If it is not the scenario, you can try to move the mailbox to another DB and test the mail flow in OWA. If the issue persists, I'd like to collect more details for investigation.
    1.Does the issue occur when sending emails to any other internal recipient of the same SMTP domain?
    2.Please run the following cmdlets and provide the outputs.

    Get-ExchangeServer | FL Name, ServerRole, *version*
                    Get-AcceptedDomain
                    Get-Mailbox -Identity user@contoso.com | FL

    3.The mail header collected from the recipient. The X-MS-Exchange-Organization-AuthAs value can indicate whether it is an internal or external email.
    4.The Message Track logs and the send connector protocol logs of this email you have got.


    Regards,

    Alex Sun


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    Friday, September 15, 2017 5:40 AM
  • It is a single server deployment, so I don't think the AD topology would affect it. There are no forwarding addresses configured or transport rules.

    I did move the user to another db but the issue persisted.

    1. The issue is happenning with a handful of users. It happens when mail is received from an external user or another internal user.

    2. 

    Name                : SERVER01
    ServerRole          : Mailbox, ClientAccess
    AdminDisplayVersion : Version 15.0 (Build 1236.3)
    ExchangeVersion     : 0.1 (8.0.535.0)

    The domain is configured as an internal relay domain w/ a send connector to gmail for non-local delivery.

    3. I do not have access to the mail headers for the affected user.

    4. From the message tracking logs:

    local user that gets routed through send connector:

    Get-MessageTrackingLog -Sender sender@domain.org -Recipients recipient@domain.org -MessageSubject "test flow 9"

    EventId  Source   Sender                            Recipients                        MessageSubject
    -------  ------   ------                            ----------                        --------------
    HARED... SMTP     sender@domain.org         {recipient@domain.org}     test flow 9
    RECEIVE  SMTP     sender@domain.org         {recipient@domain.org}     test flow 9
    AGENT... AGENT    sender@domain.org         {recipient@domain.org}     test flow 9
    TRANSFER ROUTING  sender@domain.org         {recipient@domain.org}     test flow 9
    SEND     SMTP     sender@domain.org         {recipient@domain.org}     test flow 9
    RECEIVE  STORE... sender@domain.org         {recipient@domain.org}     test flow 9
    SUBMIT   STORE... sender@domain.org         {recipient@domain.org}     test flow 9

    local user that gets delivered locally:

    Get-MessageTrackingLog -Sender sender@domain.org -Recipients recipient@domain.org -MessageSubject "test flow 9"

    EventId  Source   Sender                            Recipients                        MessageSubject
    -------  ------   ------                            ----------                        --------------
    DELIVER  STORE... sender@domain.org         {recipient@domain.org}       test flow 9
    HARED... SMTP     sender@domain.org         {recipient@domain.org}       test flow 9
    RECEIVE  SMTP     sender@domain.org         {recipient@domain.org}       test flow 9
    AGENT... AGENT    sender@domain.org         {recipient@domain.org}       test flow 9
    SEND     SMTP     sender@domain.org         {recipient@domain.org}       test flow 9
    RECEIVE  STORE... sender@domain.org         {recipient@domain.org}       test flow 9
    SUBMIT   STORE... sender@domain.org         {recipient@domain.org}       test flow 9

    The send connector logs indicate the forward to gmail as well.



    • Edited by adonerok Friday, September 15, 2017 8:52 AM
    Friday, September 15, 2017 8:05 AM
  • To close the thread, found the issue. The users in question had the targetAddress attribute set to SMTP:user@domain.org. Maybe they were converted from a contact/mail user at some point. I don't know why Exchange would choose to route it over the send connector when the address is local. One for the head scratcher.
    Monday, September 18, 2017 2:07 PM