Exchange 2016 does not send email to a smart host

Oliver ツ 1 Reputation point
2021-07-28T22:18:56.213+00:00

Hi everyone!

I have implemented Exchange 2016 on a Windows Server 2016, I am using a send connector so that the mail is sent through an antispam filter but all the sent mail is stuck in Drafts.

In the MessageTracking logs I can see the following error:

2021-07-28T20:56:31.196Z,::1,EXCH-SRVR,,mailboxtransportsubmissioninternalproxy,"MDB:1cf213fc-b792-425a-bc56-45cccf8e2e7b, Mailbox:e8ae9375-274c-4190-9602-cf1a02ac7e35, Event:95964, MessageClass:IPM.Note, CreationTime:2021-07-28T19:54:00.108Z, ClientType:OWA, SubmissionAssistant:MailboxTransportSubmissionEmailAssistant",,STOREDRIVER,SUBMITDEFER,,<******@contoso.com>,20bd2897-33c3-4ec8-0f5a-08d9520a2ca6,******@xx.gob,,,1,,,,******@contoso.com,,2021-07-28T19:54:00.108Z;LSRV=EXCH-SRVR.contoso.com:TOTAL-SUB=3751.088|SA=3750.041|MTSS=1.046(MTSSD=1.046(MTSSDA=0.009|MTSSDC=0.006|SDSSO=1.004(SMS=1.002)|X-MTSSDPL=0.006|X-MTSSDSS=0.004|MTSSDSDS=0.001)),Originating,,,,"S:ItemEntryId=00-00-00-00-58-FD-61-71-D2-81-9E-47-8C-1A-6F-18-92-6D-8B-7D-07-00-B8-28-1B-E7-4D-32-E6-45-B2-E0-1C-0D-E1-43-29-8A-00-00-00-00-01-0F-00-00-B8-28-1B-E7-4D-32-E6-45-B2-E0-1C-0D-E1-43-29-8A-00-00-0D-DE-C8-39-00-00;'S:DiagnosticInfo=Error: RetrySmtp, Diagnostic Information: Stage:UpdateMsgIdToPoisonContextMapping, SmtpResponse:451 4.4.397 Error communicating with target host. -> 421 4.2.1 Unable to connect -> SocketConnectionRefused: Socket error code 10061, details:FailedRecipientCount:0; RetryRecipientCount:0';S:DeliveryPriority=Normal",Email,5c5c285e-9b03-4892-37d0-08d9520a2d40,15.01.1466.003

But when doing a tcpdump in the antispam I don't see any connection coming from the Exchange server.

The two servers are on the same network, there is no firewall between them.

Any idea what the problem is?

Exchange | Exchange Server | Management
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2 answers

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  1. Andy David - MVP 157.8K Reputation points MVP Volunteer Moderator
    2021-07-28T22:28:41.92+00:00

    Enable SMTP Protocol logging on that send connector and see what the actual SMTP conversation is and where the anti-spam server throws the 451/421 error

    Sure the anti spam is configured to allow the Exch Server to send mail to it?

    https://learn.microsoft.com/en-us/exchange/mail-flow/connectors/configure-protocol-logging?view=exchserver-2019#use-the-eac-to-configure-protocol-logging


  2. Andy David - MVP 157.8K Reputation points MVP Volunteer Moderator
    2021-07-29T18:13:38.487+00:00

    Sitting in drafts often means a DNS issue.
    Anything set here?
    119097-image.png

    If not, what is set for DNS checking with ipconfig/all ?


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