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Sending to Group does not work if 2 external emails go to same domain RRS feed

  • Question

  • I have an Exchange 2016 group set up which works fine if I have 2 users going to different domains.

    If I add a third user going to the same domain as 1 of the others then it does not work

    Group created with email as group@mydomain.com

    e.g. User 1 - user1@gmail.com

    User 2 - user2@stoppers.org

    Works fine

    add User 3 - user3@stoppers.org

    The email to user1@gmail.com arrives perfectly ok.

    However - 2 emails are sent to stoppers.org with the TO address as group@mydomain.com which the exchange server @stoppers.org obviously cannot find and they get forwarded to admin


    Alan Friend

    Thursday, August 4, 2016 8:53 AM

Answers

  • Hi,

    Thank you for your updates.

    I find a duplication thread as you asked, and I have discussed with my colleague.

    We notice that the sender's address has been changed after user send message to group, we need find out the reason for it. Therefore, please use protocol log and message tracking log to monitor the deliver process. For your reference:
    https://technet.microsoft.com/en-us/library/aa997984(v=exchg.141).aspx
    https://technet.microsoft.com/en-us/library/aa997624%28v=exchg.150%29.aspx

    Also, please open the message header on Gmail account as your mentioned, check whether the sender's address is modified.


    Please remember to mark the replies as answers if they help, and unmark the answers if they provide no help. If you have feedback for TechNet Support, contact tnmff@microsoft.com.

    Allen Wang
    TechNet Community Support

    • Proposed as answer by Allen_WangJF Saturday, August 20, 2016 4:10 PM
    • Marked as answer by Allen_WangJF Friday, August 26, 2016 1:40 PM
    Tuesday, August 16, 2016 5:26 AM

All replies

  • Hi Alan,

    For your question, please help collect answer with below questions to narrow down this issue:
    1. Is there any error or NDR return when internal user send message to this group?
    2. How about separate send a message to each member for testing?

    Default, we can send message from to external if you create send connector to internet.
    https://technet.microsoft.com/en-us/library/jj657457%28v=exchg.160%29.aspx

    Since it works before you add second members in this DG, it indicate the mail flow is good. Then you can check the address which you added, ensure the address is valid.
    Anyway, please help to collect more details about your issue for further assistance.


    Please remember to mark the replies as answers if they help, and unmark the answers if they provide no help. If you have feedback for TechNet Support, contact tnmff@microsoft.com.

    Allen Wang
    TechNet Community Support

    Friday, August 5, 2016 7:52 AM
  • This problem occurs when sent from an internal user and there are no error messages on the sending server.

    Emails to each user individually works fine,

    Group containing user1(gmail) + user 2 only works fine.

    Group containing user1(gmail) + user 3 only works fine.

    Group containing user2 and user3 (with or without user1(gmail)) does not work


    Alan Friend


    • Edited by Al Friend Friday, August 5, 2016 8:04 AM
    Friday, August 5, 2016 8:03 AM
  • Hi

    Have you done a message track in exchange to see what happens? Do you have any custom transport rules in place?


    Edward van Biljon - Exchange MVP

    Friday, August 5, 2016 4:28 PM
  • Hi,

    Does the message queued when send message to group (contain user2 and user3)? If not, it should send NDR if deliver failed.

    Please open Queue viewer or use message tracking log (or protocol log) to get more details about this issue:
    https://technet.microsoft.com/en-us/library/aa997984(v=exchg.141).aspx
    https://technet.microsoft.com/en-us/library/aa997624%28v=exchg.150%29.aspx


    Please remember to mark the replies as answers if they help, and unmark the answers if they provide no help. If you have feedback for TechNet Support, contact tnmff@microsoft.com.

    Allen Wang
    TechNet Community Support

    Monday, August 8, 2016 3:10 AM
  • There is no NDR as the system thinks it has sent ok (but However - 2 emails are sent to stoppers.org with the TO address as group@mydomain.com which the exchange server @stoppers.org obviously cannot find and they get forwarded to admin)

    In the message tracking log - 

    EXPAND

    AGENTINFO

    TRANSFER

    SEND

    all have the 3 emails correctly

    then HAREDIRECTFAIL SMTP Inbound Proxy Probe


    Alan Friend

    Monday, August 8, 2016 8:13 AM
  • Hi, your this line is not clear - "(but However - 2 emails are sent to stoppers.org with the TO address as group@mydomain.com which the exchange server @stoppers.org "obviously cannot find" and they get forwarded to admin)"

    If I understand, these are external emails? Then did you added these external mails into "contact list" under Recipient - Contacts -  + add Mail Contacts ?


    Thanks

    Prabodha


    • Edited by PK Sarangi Monday, August 8, 2016 9:40 AM
    Monday, August 8, 2016 9:39 AM
  • Yea they are added as Mail Contacts and are members of the group


    Alan Friend

    Monday, August 8, 2016 10:09 AM
  • The exchange server @stoppers.org does not have an email address group@mydomain.com (all emails @stoppers.org are 'first name'.'surname'@stoppers.org


    Alan Friend

    Monday, August 8, 2016 10:12 AM
  • Hi,

    I notice that you can send message to each user individually works fine, then other results as you described "the exchange server @stoppers.org 'obviously cannot find'", would you please provide more details about this?

    Moreover, do you have a transport rule to forward message to your admin?
    Please run below command to check:
    Get-TransportRule| FL Name,Description


    Please remember to mark the replies as answers if they help, and unmark the answers if they provide no help. If you have feedback for TechNet Support, contact tnmff@microsoft.com.

    Allen Wang
    TechNet Community Support

    Tuesday, August 9, 2016 1:53 AM
  • Hi, you are confusing a lot!! Just let us know if "mydomain.com" is your exchange server primary domain? and you created a security group called "group" in exchange server and added all external mail contacts (firstname.surname@stoppers.org)) to this group?

    Or, is it vice versa? I mean your exchange primary domain is @stoppers.org and you try to create a group called "group@mydomain.com". If this is the case, then you need to add this "mydomain.com" into your trusted domain list, and must be a valid domain registered outside.

    Regards,

    Prabodha

    Wednesday, August 10, 2016 6:45 AM
  • The group is created on the domain (mydomain.com) and the group was created on there with the external users/emails created as Mail Contacts - the external users are valid email address @stoppers.org and I can send emails to each user individually and they arrive perfectly as expected but when I try and send to them using the group email from an account on mydomain.com the emails do not arrive as expected - 2 emails arrive @stoppers.org but the 'sent to' address is group@mydomain.com and stoppers.org does not have an account group@mydomain.com (all accounts on stoppers.org are set up as 'first name'.'surname'@stoppers.org


    Alan Friend

    Wednesday, August 10, 2016 7:56 AM
  • Hello Alan,

    Try to create a new distribution group in exchange (i.e. external@mydomain.com) with mail enabled. Add these external contacts to the group. Send a test mail from your outlook to this new group and check if mails are reaching to the recipient. 

    Thanks

    Prabodha

    Wednesday, August 10, 2016 9:41 AM
  • Done that - the 2 emails that should be sent to user1@stoppers.org and user2@stoppers.org both arrive but they are BOTH 'sent to' group@mydomain.com (and forwarded to Administrator as it cannot find the recipients)

    Alan Friend

    Wednesday, August 10, 2016 9:56 AM
  • Sorry Alan, I am not getting you properly !!

    By guessing - if you are talking mails from user2@stoppers.org not reaching to the distribution group ID, then you need to allow external mails to reach the group mail ID. To enable external mails coming to group ID: Open the distribution group properties - Mail Flow settings tab - Message Delivery Restriction - Properties - Uncheck 'Required that all senders are authenticated" and click OK.

    Good luck !

    Thanks

    Prabodha

    Wednesday, August 10, 2016 1:47 PM
  • That is the opposite of my problem.

    On myDomain.com.

    User1 - contact with external email external1@gmail.com

    User2 - contact with external email external2@stoppers.org

    MyGroup - with primary email as MyGroup@MyDomain.Com

    User1 and User2 are members of MyGroup

    Me - a user on MyDomain.com

    I can send an email to User1 - it works

    I can send an email to User2 - it works

    I can send an email to MyGroup - it works

    I then add another contact User3 - contact with external email as external3@stoppers.org

    User3 is a member of MyGroup

    I can send an email to User3 - it works

    If I now send an email to MyGroup

    User1 (gmail) - it works

    HOWEVER

    2 emails are sent to stoppers.org exchange server with the 'send-to' = MyGroup@MyDomain.Com

    - these are forwarded to administrator@stoppers.org as MyGroup@MyDomain.Com does not exist on stoppers.org


    Alan Friend

    Wednesday, August 10, 2016 2:13 PM
  • Hi,

    By default, the transport agent categorize the recipients in your environment and do not change the sender of message.

    Since this issue reproduce in new group, I want to confirm below points:
    1. Do you have any transport rule to modify sender address?
    2. Do you configure address rewriting in Edge transport server?

    Also, run below command to check the transport agent, and try to disable suspicious agent for testing:

    Get-TransportAgent


    Please remember to mark the replies as answers if they help, and unmark the answers if they provide no help. If you have feedback for TechNet Support, contact tnmff@microsoft.com.

    Allen Wang
    TechNet Community Support

    Thursday, August 11, 2016 2:14 AM
  • RunspaceId            : 880dc8e3-9fbb-420c-b8f3-71b96225b60c
    Enabled               : True
    Priority              : 1
    TransportAgentFactory : Microsoft.Exchange.MessagingPolicies.TransportRuleAgent.TransportRuleAgentFactory
    AssemblyPath          : C:\Program Files\Microsoft\Exchange Server\V15\TransportRoles\agents\Rule\Microsoft.Exchange.Me
                            ssagingPolicies.TransportRuleAgent.dll
    Identity              : Transport Rule Agent
    IsValid               : True
    ObjectState           : New

    RunspaceId            : 880dc8e3-9fbb-420c-b8f3-71b96225b60c
    Enabled               : True
    Priority              : 2
    TransportAgentFactory : Microsoft.Exchange.MessagingPolicies.DlpPolicyAgent.DlpPolicyAgentFactory
    AssemblyPath          : C:\Program Files\Microsoft\Exchange Server\V15\TransportRoles\agents\DlpPolicyAgent\Microsoft.E
                            xchange.MessagingPolicies.DlpPolicyAgent.dll
    Identity              : DLP Policy Agent
    IsValid               : True
    ObjectState           : New

    RunspaceId            : 880dc8e3-9fbb-420c-b8f3-71b96225b60c
    Enabled               : True
    Priority              : 3
    TransportAgentFactory : Microsoft.Exchange.Transport.Agent.Malware.MalwareAgentFactory
    AssemblyPath          : C:\Program Files\Microsoft\Exchange
                            Server\V15\TransportRoles\agents\Antimalware\Microsoft.Exchange.Transport.Agent.Malware.dll
    Identity              : Malware Agent
    IsValid               : True
    ObjectState           : New

    RunspaceId            : 880dc8e3-9fbb-420c-b8f3-71b96225b60c
    Enabled               : True
    Priority              : 4
    TransportAgentFactory : Microsoft.Exchange.TextMessaging.MobileDriver.TextMessagingRoutingAgentFactory
    AssemblyPath          : C:\Program Files\Microsoft\Exchange Server\V15\bin\Microsoft.Exchange.MobileDriver.dll
    Identity              : Text Messaging Routing Agent
    IsValid               : True
    ObjectState           : New

    RunspaceId            : 880dc8e3-9fbb-420c-b8f3-71b96225b60c
    Enabled               : True
    Priority              : 5
    TransportAgentFactory : Microsoft.Exchange.TextMessaging.MobileDriver.TextMessagingDeliveryAgentFactory
    AssemblyPath          : C:\Program Files\Microsoft\Exchange Server\V15\bin\Microsoft.Exchange.MobileDriver.dll
    Identity              : Text Messaging Delivery Agent
    IsValid               : True
    ObjectState           : New

    RunspaceId            : 880dc8e3-9fbb-420c-b8f3-71b96225b60c
    Enabled               : True
    Priority              : 6
    TransportAgentFactory : Microsoft.Exchange.Transport.Agent.SystemProbeDrop.SystemProbeDropSmtpAgentFactory
    AssemblyPath          : C:\Program Files\Microsoft\Exchange Server\V15\TransportRoles\agents\SystemProbeDrop\Microsoft.
                            Exchange.Transport.Agent.SystemProbeDrop.dll
    Identity              : System Probe Drop Smtp Agent
    IsValid               : True
    ObjectState           : New

    RunspaceId            : 880dc8e3-9fbb-420c-b8f3-71b96225b60c
    Enabled               : True
    Priority              : 7
    TransportAgentFactory : Microsoft.Exchange.Transport.Agent.SystemProbeDrop.SystemProbeDropRoutingAgentFactory
    AssemblyPath          : C:\Program Files\Microsoft\Exchange Server\V15\TransportRoles\agents\SystemProbeDrop\Microsoft.
                            Exchange.Transport.Agent.SystemProbeDrop.dll
    Identity              : System Probe Drop Routing Agent
    IsValid               : True
    ObjectState           : New


    Alan Friend

    Thursday, August 11, 2016 10:06 AM
  • Hi,

    Thank you for your updates.

    I find a duplication thread as you asked, and I have discussed with my colleague.

    We notice that the sender's address has been changed after user send message to group, we need find out the reason for it. Therefore, please use protocol log and message tracking log to monitor the deliver process. For your reference:
    https://technet.microsoft.com/en-us/library/aa997984(v=exchg.141).aspx
    https://technet.microsoft.com/en-us/library/aa997624%28v=exchg.150%29.aspx

    Also, please open the message header on Gmail account as your mentioned, check whether the sender's address is modified.


    Please remember to mark the replies as answers if they help, and unmark the answers if they provide no help. If you have feedback for TechNet Support, contact tnmff@microsoft.com.

    Allen Wang
    TechNet Community Support

    • Proposed as answer by Allen_WangJF Saturday, August 20, 2016 4:10 PM
    • Marked as answer by Allen_WangJF Friday, August 26, 2016 1:40 PM
    Tuesday, August 16, 2016 5:26 AM