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Mail stuck in send queue

    Question

  • Getting this error when sending email to internet:

    4.4.1 Error encuntered while communicating with primary target IP address: "Failed to connect. Winsock error code: 10060."

    Wednesday, April 17, 2019 7:05 PM

All replies

  • Hi,

    Looks like the problem is with Send connector. You can try delete and re-create the connector


    Regards From: Exchange Online | World of Cloud Computing

    Wednesday, April 17, 2019 7:08 PM
  • Re-created send connector same error, does it matter if my servers are virtual?

    Running VMware ESXI server or could this be DNS related?

    Thursday, April 18, 2019 1:45 AM
  • Hi,

    It can be a DNS issue or the smarthost issue. Check if you have port 25 connectivity fine with the smarthost


    Regards From: Exchange Online | World of Cloud Computing

    Thursday, April 18, 2019 3:17 AM
  • Did emails get stuck in the queue when sending to all the Internet domains? Is there any exception?
    Did you use smart host or the recipients' MX records to send emails to internet?

    Please run the following command to get the queue status:

    Get-Queue | fl 


    Besides, telnet the SMTP communication on port 25, run telnet <server_FQDN or IP> 25.

    For details see, Use Telnet to test SMTP communication on Exchange servers

    In addition, I have heard that disable and then enable the Ethernet Adapters on Exchange servers could sometimes do the trick. You could give a try.

    Regards, 

    Manu Meng


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    Thursday, April 18, 2019 6:33 AM
    Moderator
  • No exceptions, all emails get stuck

    Get-Queue shows same error 4.4.1

    Telnet times out to smart host and MX

    Adapter disable / enable -- no chance

    Thursday, April 18, 2019 11:13 PM
  • No exceptions, all emails get stuck

    Get-Queue shows same error 4.4.1

    Telnet times out to smart host and MX

    Adapter disable / enable -- no chance

    Telnet on port 25 failed, check if 25 port has been blocked by firewall or something else. Better confirm it with your ISP.

    Regards,

    Manu Meng


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

    Friday, April 19, 2019 9:20 AM
    Moderator
  • 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.

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    Thursday, April 25, 2019 10:29 AM
    Moderator
  • Just Finished clean install and still receiving same error ---  4.4.1 Error encuntered while communicating with primary target IP address: "Failed to connect. Winsock error code: 10060."
    Tuesday, April 30, 2019 12:18 PM
  • Found Port 25 was blocked, verified with telnet. Setup smarthost and now getting this error:

    : [{LRT=4/30/2019 6:16:14 PM};{LED=451 4.4.0 Primary target IP address responded
      with: "535 5.7.8 Error: authentication failed: UGFzc3dvcmQ6." Attempted failover to
      alternate host, but that did not succeed. Either there are no alternate hosts, or
      delivery failed to all alternate hosts.

    Checked login information in connector, all is correct but still get authentication error.

    Tuesday, April 30, 2019 10:25 PM
  • Found Port 25 was blocked, verified with telnet. Setup smarthost and now getting this error:

    : [{LRT=4/30/2019 6:16:14 PM};{LED=451 4.4.0 Primary target IP address responded
      with: "535 5.7.8 Error: authentication failed: UGFzc3dvcmQ6." Attempted failover to
      alternate host, but that did not succeed. Either there are no alternate hosts, or
      delivery failed to all alternate hosts.

    Checked login information in connector, all is correct but still get authentication error.

    It is expected you cannot get authentication with your smart host if the port 25 is blocked. If the port is confirmed be blocked, then it is necessary to open the port first and ensure your Exchange server could listen to it.

    Regards,

    Manu Meng


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

    Thursday, May 2, 2019 8:35 AM
    Moderator
  • I am getting this error with smarthost on port 587, checked with isp on alt port host, isp says exchange send connector is configured correctly. I double checked password entry to make sure it is correct, Does anyone know why I would still receive a 535 5.7.8 authentication failure error. Also verified connection on port 587 using telnet.
    Tuesday, May 7, 2019 11:56 AM
  • I am getting this error with smarthost on port 587, checked with isp on alt port host, isp says exchange send connector is configured correctly. I double checked password entry to make sure it is correct, Does anyone know why I would still receive a 535 5.7.8 authentication failure error. Also verified connection on port 587 using telnet.

    Are you using the Basic Authentication to get authenticated?

    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.

    Friday, May 10, 2019 10:09 AM
    Moderator