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Outbound not working through Google SMTP relay

    Question

  • New to Exchange.  I've got a basic 2013 server setup in my lab.  Inbound is working, routing through Google Apps SMTP relay service.  Trying to get the outbound side working, but the messages are stuck in drafts.  Looking at the queue, it doesn't look backed up (all it shows is Submission as the Next Hop Domain).  It's set to send to smtp-relay.gmail.com on port 587.  I can reach the SMTP relay on that port from the Exchange server.

    Appreciate any help


    Scott A. Jones

    Wednesday, May 17, 2017 8:22 PM

All replies

  • If you're using port 587, that usually means that you're going to configure authentication.  Have you done so?

    You might try connecting Outlook with a POP or IMAP account to the SMTP smart host and verify that you can authenticate and send mail from Outlook.  Then you can make sure your send connector has the same settings you've configured in Outlook.

    You didn't post any details about the send connector, so you should also post all its settings.

    Get-SendConnector -Identity "Connector Name" | FL


    Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."
    Celebrating 20 years of providing Exchange peer support!

    Wednesday, May 17, 2017 10:07 PM
    Moderator
  • Hi Ed - sorry for not putting the connector config in the original post.  It's below for reference.  I've tried authenticating using username/password, and also by just IP.  Both ways, nothing happens.  I did try to send directly through an email client to the smtp-relay.gmail.com servers and the message went through without a problem.

    Again, appreciate the help

    SJ

    --- BEGIN OUTPUT HERE ---

    AddressSpaces                : {SMTP:*;1}
    AuthenticationCredential     : System.Management.Automation.PSCredential
    CloudServicesMailEnabled     : False
    Comment                      :
    ConnectedDomains             : {}
    ConnectionInactivityTimeOut  : 00:10:00
    DNSRoutingEnabled            : False
    DomainSecureEnabled          : False
    Enabled                      : True
    ErrorPolicies                : Default
    ForceHELO                    : False
    Fqdn                         : mail.ciscocollabguru.com
    FrontendProxyEnabled         : False
    HomeMTA                      : Microsoft MTA
    HomeMtaServerId              : EXCHANGE
    Identity                     : google
    IgnoreSTARTTLS               : False
    IsScopedConnector            : False
    IsSmtpConnector              : True
    MaxMessageSize               : 35 MB (36,700,160 bytes)
    Name                         : google
    Port                         : 587
    ProtocolLoggingLevel         : None
    RequireOorg                  : False
    RequireTLS                   : False
    SmartHostAuthMechanism       : None
    SmartHosts                   : {smtp-relay.gmail.com}
    SmartHostsString             : smtp-relay.gmail.com
    SmtpMaxMessagesPerConnection : 20
    SourceIPAddress              : 0.0.0.0
    SourceRoutingGroup           : Exchange Routing Group (DWBGZMFD01QNBJR)
    SourceTransportServers       : {EXCHANGE}
    TlsAuthLevel                 :
    TlsCertificateName           :
    TlsDomain                    :
    UseExternalDNSServersEnabled : True

    --- END OUTPUT HERE ---


    Scott A. Jones

    Thursday, May 18, 2017 12:15 AM
  • Your configuration appears to be consistent with Google's documentation. Are you sure you've configured your Exchange server's outbound SMTP address properly in Gmail?  You might also try port 25 since Google's documentation for connecting by an Exchange server doesn't appear to require port 587.


    Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."
    Celebrating 20 years of providing Exchange peer support!

    Thursday, May 18, 2017 11:45 PM
    Moderator
  • Good point. Going to try that next, along with TLS for grins...something odd though. I've got verbose logging on for my send connector, but there's nothing at all in the log folder. Almost like it's not trying to do anything at all. Hopefully the port change will trigger something to happen but if that raises any additional flags, let me know what you think. Thanks again!

    Scott A. Jones

    Friday, May 19, 2017 4:17 PM
  • Make sure you look in the right folder for the logging.

    Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."
    Celebrating 20 years of providing Exchange peer support!

    Saturday, May 20, 2017 11:15 PM
    Moderator