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Relay Issue - Exchange 2016 On-Prem Hybrid O365 RRS feed

  • Question

  • We have an on-prem Exchange 2016 set up as a SMTP relay.  We have an issue when trying to send notifications through the relay to "in cloud" distribution groups (works fine for any group created onprem).  For whatever reason, the on-prem SMTP will not send emails to cloud only distribution list saying the email address you entered couldn't be found.  I can email to this address via outlook .

    Remote Server returned '550 5.1.10 RESOLVER.ADR.RecipientNotFound; Recipient not found by SMTP address lookup'

    So i know this has to do with the connectors but I really do not know how to resolve this.  So any help would be great!

    Thursday, December 6, 2018 1:06 PM

Answers

  • So I checked the sender and receiver connectors and they look to be configured correctly based on posts up above.  I is there any risk in running the hybrid config again?  I inherited this server so I do not know if its current stay is configured correctly.

    Thanks,

    Jon

    Re-run HCW should be fine, it will fix any issue on the connector during the configuration.

    Besides, could the email be relayed from Exchange on-premises user to O365 individual users(not groups)? 
    And how about sending email directly from Exchange on-premises user to O365 groups or users.

    Regards,

    Manu Meng


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    • Marked as answer by Joho1981 Friday, December 21, 2018 5:36 PM
    Monday, December 17, 2018 7:31 AM

All replies

  • It seems that distribution groups are not syncing to Office 365. Please check AAD connector and confirm if groups are syncing to Office 365.

    You can test group presence by running below command:-

    On-prem

    Get-recipient "group"

    Online:-

    Get-MsolGroup -SearchString 'Group"

    Thursday, December 6, 2018 2:32 PM
  • We have an on-prem Exchange 2016 set up as a SMTP relay.  We have an issue when trying to send notifications through the relay to "in cloud" distribution groups (works fine for any group created onprem).  For whatever reason, the on-prem SMTP will not send emails to cloud only distribution list saying the email address you entered couldn't be found.  I can email to this address via outlook .

    Remote Server returned '550 5.1.10 RESOLVER.ADR.RecipientNotFound; Recipient not found by SMTP address lookup'

    So i know this has to do with the connectors but I really do not know how to resolve this.  So any help would be great!

    Do you have a send connector address space for the "cloud" SMTP domains? 
    Thursday, December 6, 2018 2:38 PM
  • It seems that distribution groups are not syncing to Office 365. Please check AAD connector and confirm if groups are syncing to Office 365.

    You can test group presence by running below command:-

    On-prem

    Get-recipient "group"

    Online:-

    Get-MsolGroup -SearchString 'Group"

    If these are cloud only groups, there would be no sync from on-prem.
    Thursday, December 6, 2018 4:10 PM
  • We have an on-prem Exchange 2016 set up as a SMTP relay.  We have an issue when trying to send notifications through the relay to "in cloud" distribution groups (works fine for any group created onprem).  For whatever reason, the on-prem SMTP will not send emails to cloud only distribution list saying the email address you entered couldn't be found.  I can email to this address via outlook .

    Remote Server returned '550 5.1.10 RESOLVER.ADR.RecipientNotFound; Recipient not found by SMTP address lookup'

    So i know this has to do with the connectors but I really do not know how to resolve this.  So any help would be great!

    Do you have a send connector address space for the "cloud" SMTP domains? 

    Agree with Andy, since on-premises group can receive the email, the smtp relay receive connector should work fine, we should check the send connector on the on-premises sever.

    Get-SendConnector | fl


    Regards, 

    Manu Meng


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

    Click here to learn more. Visit the dedicated forum to share, explore and talk to experts about Microsoft Teams.

    • Proposed as answer by Manu Meng Monday, December 10, 2018 10:06 AM
    Friday, December 7, 2018 7:48 AM
  • Just checking in to see if above information was helpful. Please let us know if you would like further assistance.

    Regards, 

    Manu Meng


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

    Click here to learn more. Visit the dedicated forum to shareexplore and talk to experts about Microsoft Teams.

    Tuesday, December 11, 2018 9:38 AM
  • Sorry was off work the last few days.  I am looking over the replys now to see if any of them will correct the issue I am seeing.  Thanks
    Tuesday, December 11, 2018 12:55 PM
  • Sorry was off work the last few days.  I am looking over the replys now to see if any of them will correct the issue I am seeing.  Thanks

    Did you check the connector setting in your on-premises server? It is created when you run HCW, so re-run HCW could be an option.

    Regards,

    Manu Meng


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

    Click here to learn more. Visit the dedicated forum to share, explore and talk to experts about Microsoft Teams.

    Thursday, December 13, 2018 10:24 AM
  • So I checked the sender and receiver connectors and they look to be configured correctly based on posts up above.  I is there any risk in running the hybrid config again?  I inherited this server so I do not know if its current stay is configured correctly.

    Thanks,

    Jon

    Thursday, December 13, 2018 3:47 PM
  • So I checked the sender and receiver connectors and they look to be configured correctly based on posts up above.  I is there any risk in running the hybrid config again?  I inherited this server so I do not know if its current stay is configured correctly.

    Thanks,

    Jon

    Re-run HCW should be fine, it will fix any issue on the connector during the configuration.

    Besides, could the email be relayed from Exchange on-premises user to O365 individual users(not groups)? 
    And how about sending email directly from Exchange on-premises user to O365 groups or users.

    Regards,

    Manu Meng


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

    Click here to learn more. Visit the dedicated forum to share, explore and talk to experts about Microsoft Teams.

    • Marked as answer by Joho1981 Friday, December 21, 2018 5:36 PM
    Monday, December 17, 2018 7:31 AM
  • So after multiple attempts I have settled on using smtp via IIS.  Besides the fact of this working it also allows me to delete our onprem exchange server :).  Thanks everyone for the help and ideas!
    Friday, December 21, 2018 5:35 PM