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Outbound TLS authentication failed with error RevocationOffline for Send connector internet mail: EX 2016 SEND CONNECTOR

Benard Mwanza 1,001 Reputation points
2021-12-02T10:16:53.81+00:00

I get the following error, its being logged in application logs.

Outbound TLS authentication failed with error RevocationOffline for Send connector internet mail. The TLS authentication mechanism is CertificateValidation. Target is mysmarthost.mydomain.com.

Internet mail is my send connector name.

Event 2022, MSExchangeTransport.

My send connector is assigned valid SSL certificate.

What's the cause of this error and its impact.

I'm unable to receive emails.
From ms remote connectivity analyzer inbound smtp test i get the following details.

The server returned status code 554 - Transaction failed. The server response was: Spam email. Email Session ID: {61A8A5A8-12-BDBE813A-CF423680} Exception details: Message: Transaction failed. The server response was: Spam email. Email Session ID: {61A8A5A8-12-BDBE813A-CF423680} Type: System.Net.Mail.SmtpException Stack trace: at System.Net.Mail.SmtpConnection.GetConnection(ServicePoint servicePoint) at System.Net.Mail.SmtpClient.GetConnection() at System.Net.Mail.SmtpClient.Send(MailMessage message) at Microsoft.M365.RCA.ConnectivityTests.SmtpMessageTest.PerformTestReally()

Exchange Server Management
Exchange Server Management
Exchange Server: A family of Microsoft client/server messaging and collaboration software.Management: The act or process of organizing, handling, directing or controlling something.
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  1. Benard Mwanza 1,001 Reputation points
    2021-12-09T12:00:04.427+00:00

    I managed to resolve the issue. my smart host is not trusted by my exchange server. I just needed to install certificate in smart host to encrypt communication between the smarthost and exchange server

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  1. Joyce Shen - MSFT 16,651 Reputation points
    2021-12-03T02:32:05.137+00:00

    Hi @Benard Mwanza

    For the status code 554, it can be caused by

    • The server thinks this email is spam or server IP address has been blacklisted
    • A spam trap identifying your machine as a relay, or as a machine not trusted to send mail from your domain.

    And please make sure the certificate you are using is a valid 3rd party certificate.

    You could try removing the existing send connector, then rerun HCW to recreate a new one 

      $cert = Get-ExchangeCertificate -Thumbprint <Thumbprint>  
  $tlscertificatename = "<i>$($cert.Issuer)<s>$($cert.Subject)"  
  Set-ReceiveConnector "EX2016SRV1\HybridRecConnector" -TlsCertificateName $tlscertificatename  
  Set-SendConnector -Identity “Send Connector Name” -TLSCertificateName $tlscertificatename

    Below is a thread discussed the similar issue: outbound tls authentication failed for auth level domainvalidation with error revocationoffline

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