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Mail stuck in Outlook outbox

    Question

  • Hi,

     i have a exchange 2013 environment giving me this problem. I did not install this env. This environment was earlyer a DAG with

     two exchange servers both servers having all roles installed. Now I have removed the DAG and there i only one exchange server 

     with all roles. This problem started after I removed the DAG. I have increased the memory so I do not think this is because of

     lack of resources. The system will recover after ca 30 min. Restarting the transport service. There is nothing in eventlogs.

     So what is the best thing I can do regarding this. I have seen someone mention to delete receive connector and recreate them

     again not using the HubTransport but use FrontendTransport insted??

     His is how this looks,

    PS] C:\Windows\system32>Get-ReceiveConnector

    Identity                                Bindings

    --------                                --------

    EXCH03\Default EXCH03                           {0.0.0.0:2525, [::]:2525}

    EXCH03\Client Proxy EXCH03              {[::]:465, 0.0.0.0:465}

    EXCH03\Default Frontend EXCH03          {[::]:25, 0.0.0.0:25}

    EXCH03\Outbound Proxy Frontend EXCH03   {[::]:717, 0.0.0.0:717}

    EXCH03\Client Frontend EXCH03           {[::]:587, 0.0.0.0:587}

    EXCH03\AnonSMTPRelay                      {0.0.0.0:25}

    EXCH03\Comendo reinjection             {0.0.0.0:25}

    EXCH03\RR-SCWEB01 Relay                 {0.0.0.0:25}

    EXCH03\ScanReley                                  {0.0.0.0:25}

    C:\Windows\system32>netstat -aon | find ":25 "

      TCP    0.0.0.0:25             0.0.0.0:0              LISTENING       6840

      TCP    10.141.1.32:25         192.168.250.251:54771  TIME_WAIT       0

      TCP    [::]:25                [::]:0                 LISTENING       6840

     pls adv



    Erro

    Monday, January 4, 2016 8:18 PM

Answers

  • Hi,

    Please confirm whether the issue happens to all outlook users or a specific user to narrow down the issue.

    Also check if you can send the emails fine on OWA.

    Have you tried to restart the Transport Service?

    Please check if you can find the queued message in the queue viewer.

    Also temporarily disable firewall and antivirus software to test .

    Regards,

    David 


    Tuesday, January 5, 2016 3:18 AM
    Moderator

All replies

  • Receive connectors would have nothing to do with email staying in the Outbox.

    That is usually a transport issue.

    Do you see messages stuck in the queues when email isn't leaving the environment? Is the server fully up to date with the latest updates? If you have AV software on the server, does it have the correct exclusions in it for Exchange?

    Simon.


    Simon Butler, Exchange MVP
    Blog | Exchange Resources | In the UK? Hire Me.

    Monday, January 4, 2016 9:04 PM
  • Hi,

    Please confirm whether the issue happens to all outlook users or a specific user to narrow down the issue.

    Also check if you can send the emails fine on OWA.

    Have you tried to restart the Transport Service?

    Please check if you can find the queued message in the queue viewer.

    Also temporarily disable firewall and antivirus software to test .

    Regards,

    David 


    Tuesday, January 5, 2016 3:18 AM
    Moderator
  • Hi,

    Check the Application Windows event log and see if there are related warnings are logged. Also, see the result of Test-ServiceHealth and see if there are some issues to any of the services


    Regards From: Exchange Online | Windows Administrator's Area

    Tuesday, January 5, 2016 4:29 AM
  •  Hi David,

      this happens to all Outlook users. The only quick way to get this working again is to restart the Transport service.

      This can happen 3-4 times a day and some days never. I have not tested sending mail with OWA.

     


    Erro

    Tuesday, January 5, 2016 6:48 AM
  •  Hi,

     I have not seen anything suspicious in Application Windows event log.

     This is the result of the test.. the system is working perfectly when the test was taken.

     [PS] C:\Windows\system32>Test-ServiceHealth


    Role                    : Mailbox Server Role
    RequiredServicesRunning : True
    ServicesRunning         : {IISAdmin, MSExchangeADTopology, MSExchangeDelivery, MSExchangeIS, MSExchangeMailboxAssistant
                              s, MSExchangeRepl, MSExchangeRPC, MSExchangeServiceHost, MSExchangeSubmission, MSExchangeThro
                              ttling, MSExchangeTransportLogSearch, W3Svc, WinRM}
    ServicesNotRunning      : {}

    Role                    : Client Access Server Role
    RequiredServicesRunning : True
    ServicesRunning         : {IISAdmin, MSExchangeADTopology, MSExchangeMailboxReplication, MSExchangeRPC, MSExchangeServi
                              ceHost, W3Svc, WinRM}
    ServicesNotRunning      : {}

    Role                    : Unified Messaging Server Role
    RequiredServicesRunning : True
    ServicesRunning         : {IISAdmin, MSExchangeADTopology, MSExchangeServiceHost, MSExchangeUM, W3Svc, WinRM}
    ServicesNotRunning      : {}

    Role                    : Hub Transport Server Role
    RequiredServicesRunning : True
    ServicesRunning         : {IISAdmin, MSExchangeADTopology, MSExchangeEdgeSync, MSExchangeServiceHost, MSExchangeTranspo
                              rt, MSExchangeTransportLogSearch, W3Svc, WinRM}
    ServicesNotRunning      : {}





    Erro

    Tuesday, January 5, 2016 6:54 AM
  •   Hi,

       I will check all exclusions to make sure it is correct.

        I checked the exclusion list, ran a script to find all that is need to exclude on the exchange server.

         The script came up with a lot of files and folders which i have inserted to my AV exclusion list.

          This is more detailed list than I had before, maybe this will help.


    Erro


    • Edited by Erró Tuesday, January 5, 2016 10:00 AM
    Tuesday, January 5, 2016 8:25 AM
  • hi,

     after udating the AV I still get this problem. All mail stuck in outbox for every user, had to restart transport service to get it started again.

    This is how listening status looks on port 25, could this be the problem??


    C:\Windows\system32>netstat -aon | find ":25 "
      TCP    0.0.0.0:25             0.0.0.0:0              LISTENING       6840
      TCP    10.141.1.32:25         10.199.24.20:11631     ESTABLISHED     6840
      TCP    10.141.1.32:25         10.199.24.20:13846     TIME_WAIT       0
      TCP    10.141.1.32:25         192.168.250.251:65385  TIME_WAIT       0
      TCP    10.141.1.32:29953      10.141.1.32:25         TIME_WAIT       0
      TCP    10.141.1.32:29954      10.141.1.32:25         TIME_WAIT       0
      TCP    10.141.1.32:30170      10.141.1.32:25         TIME_WAIT       0
      TCP    10.141.1.32:30171      10.141.1.32:25         TIME_WAIT       0
      TCP    [::]:25                [::]:0                 LISTENING       6840


    [PS] C:\Scrips>Test-ServiceHealth


    Role                    : Mailbox Server Role
    RequiredServicesRunning : True
    ServicesRunning         : {IISAdmin, MSExchangeADTopology, MSExchangeDelivery, MSExchangeIS, MSExchangeMailboxAssistant
                              s, MSExchangeRepl, MSExchangeRPC, MSExchangeServiceHost, MSExchangeSubmission, MSExchangeThro
                              ttling, MSExchangeTransportLogSearch, W3Svc, WinRM}
    ServicesNotRunning      : {}

    Role                    : Client Access Server Role
    RequiredServicesRunning : True
    ServicesRunning         : {IISAdmin, MSExchangeADTopology, MSExchangeMailboxReplication, MSExchangeRPC, MSExchangeServi
                              ceHost, W3Svc, WinRM}
    ServicesNotRunning      : {}

    Role                    : Unified Messaging Server Role
    RequiredServicesRunning : True
    ServicesRunning         : {IISAdmin, MSExchangeADTopology, MSExchangeServiceHost, MSExchangeUM, W3Svc, WinRM}
    ServicesNotRunning      : {}

    Role                    : Hub Transport Server Role
    RequiredServicesRunning : True
    ServicesRunning         : {IISAdmin, MSExchangeADTopology, MSExchangeEdgeSync, MSExchangeServiceHost, MSExchangeTranspo
                              rt, MSExchangeTransportLogSearch, W3Svc, WinRM}
    ServicesNotRunning      : {}

    [PS] C:\Scrips>

    here how it looks after i restarted Exchange Transport service

    \Windows\system32>netstat -aon | find ":25 "
    TCP    0.0.0.0:25             0.0.0.0:0              LISTENING       6840
    TCP    10.141.1.32:25         10.199.24.20:53570     ESTABLISHED     6840
    TCP    10.141.1.32:25         192.168.250.251:63175  TIME_WAIT       0
    TCP    [::]:25                [::]:0                 LISTENING       6840


    Erro


    • Edited by Erró Wednesday, January 6, 2016 11:03 AM
    Wednesday, January 6, 2016 10:57 AM
  • Hi,

    According to your description, the issue may be related to the transport service side.

    For further troubleshooting, please use the Set-EventLogLevel cmdlet to set the event log level high and check if we can find some error related to transport service.

    https://technet.microsoft.com/en-us/library/aa998905%28v=exchg.160%29.aspx?f=255&MSPPError=-2147217396

    Regards,

    David 


    Thursday, January 7, 2016 9:52 AM
    Moderator