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Delivery is delayed message

    Question

  • We are having issues sending emails from our Exchange Server. I sent some test emails this morning and a couple hours later they came back saying "Delivery is delayed " What can I do to troubleshoot this issue? Any help will be greatly appreciated. 
    Tuesday, October 18, 2016 7:46 PM

Answers

  • Thanks for your reply and sharing.

    The issue may occur:

    1. The remote server is configured not provide STARTTLS command

    2. The firewall filter the STARTTLS command

    Please keep updating. If the reply helped, please help to mark as answer, it'll be helpful and easily to search for others, thanks for your time. Please let us know if you would like further assistance.

    BR.


    Jason Chao
    TechNet Community Support


    Please remember to mark the replies as an answer if they help and unmark them if they provide no help.
    If you have feedback for TechNet Subscriber Support, contact tnmff@microsoft.com

    • Proposed as answer by Jason.Chao Wednesday, October 26, 2016 2:37 AM
    • Marked as answer by Jason.Chao Friday, October 28, 2016 9:53 AM
    Thursday, October 20, 2016 10:04 AM

All replies

  • Go to EMC and then to Toolbox and open up Queue Viewer to see if there is any mails stuck in queue.
    • Edited by Niten Kumar Tuesday, October 18, 2016 7:50 PM
    Tuesday, October 18, 2016 7:50 PM
  • We have 878 messages stuck that you can see in the snapshot below. I recently set up a relay connector that is pointed to our CipaFilter (filters content and emails for our users). We just decided to use the CipaFilter to filter content and spam for emails. I've never set up a connector before so I might have done it wrong. I also inserted a snapshot of the relay connector config. Could you look at it and let me know if it is right? The CipaFilter's ip is 10.1.0.1

    

    Tuesday, October 18, 2016 8:21 PM
  • What's the error message coming up in the queue viewer next to relay connector queue?

    Or "Get-Queue | FL" to find all the properties of the queue and look for the LastError...

    Did you consult CipaFilter to find the correct way to setup connector with them and any guidance from them?


    Amit Tank | Office Servers and Services - MVP | Blog: exchangeshare.wordpress.com


    • Edited by Amit Tank Wednesday, October 19, 2016 12:33 AM
    Wednesday, October 19, 2016 12:32 AM
  • Hi jkepple,

    It seems your emails are stuck in the queue. As Amit mentioned, you can use the command to get the last error.

    You can also check the Protocol log in the following path:

    C:\Program Files\Microsoft\Exchange Server\V14\TransportRoles\Logs\ProtocolLog\SmtpSend

    Please post out in detail if any errors exist.

    BR.



    Jason Chao
    TechNet Community Support


    Please remember to mark the replies as an answer if they help and unmark them if they provide no help.
    If you have feedback for TechNet Subscriber Support, contact tnmff@microsoft.com

    Wednesday, October 19, 2016 7:46 AM
  • The last error says "451 4.4.0 Primary target IP address responded with: "451 5.7.3 Require STARTTLS to do basic authentication." Attempted failover to alternate host, but that did not succeed. Either there are no alternate hosts, or delivery failed to all alternate hosts."

    It sounds like the connector's authentication isn't set right. CipaFilter's support has been taking 8 hours to get back to me but it looks like I'll have to get a hold of them and see what they say. I don't think the guy from Cipa that I've been emailing about this issue knows a whole lot about it because he gave me a link with instructions on how to create a connector for Exchange 2013 but we have 2012. So I had to find instructions myself. haha 

    Thanks for your help I think this really narrows it down.

    Wednesday, October 19, 2016 1:21 PM
  • Thanks for your reply and sharing.

    The issue may occur:

    1. The remote server is configured not provide STARTTLS command

    2. The firewall filter the STARTTLS command

    Please keep updating. If the reply helped, please help to mark as answer, it'll be helpful and easily to search for others, thanks for your time. Please let us know if you would like further assistance.

    BR.


    Jason Chao
    TechNet Community Support


    Please remember to mark the replies as an answer if they help and unmark them if they provide no help.
    If you have feedback for TechNet Subscriber Support, contact tnmff@microsoft.com

    • Proposed as answer by Jason.Chao Wednesday, October 26, 2016 2:37 AM
    • Marked as answer by Jason.Chao Friday, October 28, 2016 9:53 AM
    Thursday, October 20, 2016 10:04 AM