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Delivery is delayed error when sending to a particular address.

    Question


  • We have been running 2 Exchange 2010 servers for about 1 year.  Very few problems.  However, I had a user today that complained of this error:  Delivery is delayed to these recipients or groups:...

    I sent a test message to the intended recipient and he got the message.  Then I had the user send a test msg and it worked too.  So I thought the problem was solved.  However, later we got another "delayed error" from a different msg sent to this recipient.  So I used message tracking to troubleshoot the problem.  Below is what I found on the delayed message.  What might be going on and what else can I do to troubleshoot this issue?  thanks

    Submitted
    5/8/2013 10:54 AM POLY-E10-1.corp.domain.com
    The message was submitted to poly-e10-2.corp.domain.com. Pending

    5/8/2013 10:54 AM poly-e10-2.corp.domain.com
    The message has been queued on server 'poly-e10-2.corp.domain.com' since 5/8/2013 10:54:59 AM (UTC-06:00) Central Time (US & Canada). The last attempt to send the message was at 5/8/2013 3:11:33 PM (UTC-06:00) Central Time (US & Canada) and generated the error '400 4.4.7 Message delayed'.

    5/8/2013 3:22 PM poly-e10-2.corp.domain.com
    Message delivery is taking longer than expected. There may be system delays. For more information, contact your helpdesk.
    Wednesday, May 08, 2013 8:40 PM

Answers

  • On Thu, 9 May 2013 14:25:27 +0000, Poly Admin wrote:
     
    >
    >
    >I did not see anything in the article to help me. I am not sure what you mean by "Please your exchange server can send mail to the domain." What does this mean?
    >
    >When we send messages to this address sometimes they are delivered and sometimes they are not. Very strange problem. For instance I sent a message at 10:22 AM and it went thru successfully, but a msg I sent at sent at 10:54 AM was and still is delayed.
    >
    >I need to determine if it is my Exchange server or the other end. Thanks for any help.
     
    Have a look at the SMTP Send protocol log. You know the recipient's
    address and the approximate time you sent the message so finding it
    shouldn't be difficult.
     
    Does you server try to send the message and receives no 220 banner
    from the target server? Does it send a HELO/EHLO and get no response?
    Does the server get to the DATA (or BDAT) and start sending the
    message but never finishes? Do you get 4xx status codes from the
    target server?
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    Saturday, May 11, 2013 1:24 AM
  • On Wed, 22 May 2013 15:11:41 +0000, Poly Admin wrote:
     
    >
    >
    >The tracert completed successfully even with the 1st window sitting there with the blinking cursor. Closed the 1st telnet window and opened up another and the telnet command got the 220 smtp banner perfectly.
    >
    >Thanks for your help. It appears that my email system is working properly so I am not sure what else I can do. Should we just close this issue and call it an anomaly?
     
    Sure.
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    • Marked as answer by Poly Admin Thursday, May 23, 2013 1:30 PM
    Thursday, May 23, 2013 1:53 AM

All replies

  • Hi  ,

    I noticed, '400 4.4.7 Message delayed' and “Message delivery is taking longer than expected. There may be system delays.”

    Message wait time in queue exceeds limit. Please your exchange server can send email to the domain.

    400 4.4.7 Message delayed:

    http://social.technet.microsoft.com/forums/en-US/exchangesvr3rdpartyappslegacy/thread/ac212184-49c5-459c-8d9d-4529c176e012/

    If you have any feedback on our support, please click here


    Wendy Liu
    TechNet Community Support

    Thursday, May 09, 2013 7:23 AM
  • I did not see anything in the article to help me.  I am not sure what you mean by "Please your exchange server can send mail to the domain."  What does this mean?

    When we send messages to this address sometimes they are delivered and sometimes they are not.  Very strange problem.  For instance I sent a message at 10:22 AM and it went thru successfully, but a msg I sent at sent at 10:54 AM was and still is delayed.

    I need to determine if it is my Exchange server or the other end.  Thanks for any help.

    Thursday, May 09, 2013 2:25 PM
  • On Thu, 9 May 2013 14:25:27 +0000, Poly Admin wrote:
     
    >
    >
    >I did not see anything in the article to help me. I am not sure what you mean by "Please your exchange server can send mail to the domain." What does this mean?
    >
    >When we send messages to this address sometimes they are delivered and sometimes they are not. Very strange problem. For instance I sent a message at 10:22 AM and it went thru successfully, but a msg I sent at sent at 10:54 AM was and still is delayed.
    >
    >I need to determine if it is my Exchange server or the other end. Thanks for any help.
     
    Have a look at the SMTP Send protocol log. You know the recipient's
    address and the approximate time you sent the message so finding it
    shouldn't be difficult.
     
    Does you server try to send the message and receives no 220 banner
    from the target server? Does it send a HELO/EHLO and get no response?
    Does the server get to the DATA (or BDAT) and start sending the
    message but never finishes? Do you get 4xx status codes from the
    target server?
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    Saturday, May 11, 2013 1:24 AM
  • Ok, I just went to EMC, Organization Configuration, Hub Transport, Send Connectors, properties of my Send Connector, and set Protocol Logging level to Verbose.  Is was turned off.  I will send another test email to the address that is being delayed.  Then I can check the log.  I will let you know the results later today and maybe you can then help me determine what is going on.  thank you
    Monday, May 13, 2013 3:10 PM
  • I don't fully understand what to expect from the logs but I have 2 exchange 2010 servers that both can send outbound mail, and I have had the logging turned on for over an hour now but the test msg I sent is not showing up anywhere in the send log(s).  I have looked on both servers.  It appears that even though my mailbox is on Server-1 that my messages are being sent out of Server-2.  Don't know why.  Some of my sent messages are showing up in the logs but not the delayed message.

    My logging properties for "smtp send" are set to the Lowest level.  Should I increase the logging level to Med, High, or Expert?  I would expect Send errors to be in the log even at the lowest level.  Maybe not. 

    Let me know what you think and what else I need to do.   thanks


    • Edited by Poly Admin Monday, May 13, 2013 7:33 PM
    Monday, May 13, 2013 4:47 PM
  • >On Mon, 13 May 2013 16:47:01 +0000, Poly Admin wrote:
     
    >I don't fully understand what to expect from the logs but I have 2 exchange 2010 servers that both can send outbound mail, and I have had the logging turned on for over an hour now but the test msg I sent is not showing up anywhere in the send log(s). I have looked on both servers.
     
    Is it in any of the delivery queues? If it is, what's the last errror?
     
    >It appears that even though my mailbox is on Server-1 that my messages are being sent out of Server-2. Don't know why.
     
    That's expected. If you have co-located mailbox and hub transport
    roles the mailbox role prefers using a hub transport on another
    server. In that way a server failure won't stop the delivery of the
    message.
     
    >Some of my sent messages are showing up in the logs but not the delayed message.
     
    Look for the message in the message tracking log on the mailbox
    server. You should find a SUBMIT event. You can follow the message
    from there to the HT server,
     
    >My logging properties for "smtp send" are set to the Lowest level. Should I increase the logging level to Med, High, or Expert? I would expect Send errors to be in the log even at the lowest level. Maybe not.
    >
    >Let me know what you think and what else I need to do. thanks
     
    First you need to locate the HT server that's responsible for handling
    the message. From there you should be able to find any activity in the
    SMTP send protocol log if the server's connecting to the next hop.
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    Tuesday, May 14, 2013 1:53 AM
  • Is it in any of the delivery queues? If it is, what's the last errror?

    A:  400 4.4.7 Message delayed

    >Some of my sent messages are showing up in the logs but not the delayed message.
     
    Look for the message in the message tracking log on the mailbox
    server. You should find a SUBMIT event. You can follow the message
    from there to the HT server,

    I am looking in here (D:\Exchange Server\2010\TransportRoles\Logs\MessageTracking) at yesterdays log file.  I am finding a reference to the email I sent to but no SUBMIT event.  Am I in the wrong log?
     
    >My logging properties for "smtp send" are set to the Lowest level. Should I increase the logging level to Med, High, or Expert? I would expect Send errors to be in the log even at the lowest level. Maybe not.
     
    First you need to locate the HT server that's responsible for handling
    the message. From there you should be able to find any activity in the
    SMTP send protocol log if the server's connecting to the next hop.

    I am looking on the server that is trying to send the message.  I am looking here (D:\Exchange Server\2010\TransportRoles\Logs\ProtocolLog\SmtpSend) at yesterdays file and I find no reference of the email address I am trying to send to.  So I see the reference to the message in the message tracking log but not in the send log.  Why??

    From the question above remember is is queued with error "400 4.4.7 Message delayed"

    This is driving me insane!!  But thank you for your help.
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP

    Tuesday, May 14, 2013 2:15 PM
  • On Tue, 14 May 2013 14:15:10 +0000, Poly Admin wrote:
     
    >>Is it in any of the delivery queues? If it is, what's the last errror?
    >
    >A: 400 4.4.7 Message delayed
     
    That's not very helpful, is it? :-)
     
    If you right-click the queue and select "Retry" do you get different
    error after a few minutes when the queue goes back to the "retry"
    state?
     
    >Some of my sent messages are showing up in the logs but not the delayed message.
     
    >>Look for the message in the message tracking log on the mailbox server. You should find a SUBMIT event. You can follow the message from there to the HT server,
     
    >I am looking in here (D:\Exchange Server\2010\TransportRoles\Logs\MessageTracking) at yesterdays log file. I am finding a reference to the email I sent to but no SUBMIT event. Am I in the wrong log?
     
    On a mailbox server there are MSGTRKM*.log files. They contain the
    SUBMIT events. On a hub transport server there are MSGTRK*.log (no 2nd
    "M" in the name). But you should really be using the Tracking Log
    Explorer or the get-messagetrackinglog cmdlet. Mucking around in the
    log files themselves is okay if you know what you're looking for, but
    it's usually confusing if this is your first foray into log files. :-)
     
    >My logging properties for "smtp send" are set to the Lowest level. Should I increase the logging level to Med, High, or Expert? I would expect Send errors to be in the log even at the lowest level. Maybe not.
     
    Those logging levels manage the events recorded in the Applications
    Event Log, not the Message Tracking or SMTP protocol logs.
     
    >>First you need to locate the HT server that's responsible for handling the message. From there you should be able to find any activity in the SMTP send protocol log if the server's connecting to the next hop. I am looking on the server that is trying to send the message.
     
    >I am looking here (D:\ExchangeServer\2010\TransportRoles\Logs\ProtocolLog\SmtpSend) at yesterdays file and I find no reference of the email address I am trying to send to. So I see the reference to the message in the message tracking log but not in the send log.
     
    That's a good thing. What are the events and sources you see?
     
    >Why??
     
    If the message never makes it to the SEND/SMTP event then it's still
    in the categorizer.
     
    For a message that's sent you should see this sequence of Event/Source
    in the message tracking log if everything's on the same machine:
     
    SUBMIT/STOREDRIV
    RECEIVE/STOREDRV
    TRANSFER/ROUTING
    SEND/SMTP
     
    >From the question above remember is is queued with error "400 4.4.7 Message delayed" This is driving me insane!! But thank you for your help.
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    Wednesday, May 15, 2013 1:04 AM
  • On Tue, 14 May 2013 14:15:10 +0000, Poly Admin wrote:
     
    *Even though I have not been able to correct this issue, I really appreciate you helping with this.*
     
    >If you right-click the queue and select "Retry" do you get different
    error after a few minutes when the queue goes back to the "retry"
    state?

    A: From within the EMC, Toolbox, I go into the Q viewer.  I connect to the server that is trying to send the message.  I see companyname.com listed under the Queues tab.  The only option I have are: View message, suspend, or Remove messages with or without NDR.  I don't see an option to "Retry".
     
     
    >On a mailbox server there are MSGTRKM*.log files. They contain the
    SUBMIT events. On a hub transport server there are MSGTRK*.log (no 2nd
    "M" in the name). But you should really be using the Tracking Log
    Explorer or the get-messagetrackinglog cmdlet. Mucking around in the
    log files themselves is okay if you know what you're looking for, but

    it's usually confusing if this is your first foray into log files. :-)

    A:  Ok, I used the Tracking Log Explorer and I searched for the delayed message using the tool.  I found the message and I have two lines of message tracking results.  But it doesn't show an error.  Just timestamp, event id, source, etc.  What am I looking for?
    This is what was listed in the Event ID and Source:
    RECEIVE  STOREDRIVER
    TRANSFER  ROUTING

     
    >First you need to locate the HT server that's responsible for handling the message. From there you should be able to find any activity in the SMTP send protocol log if the server's connecting to the next hop.
     
    >I am looking here (D:\ExchangeServer\2010\TransportRoles\Logs\ProtocolLog\SmtpSend) at yesterdays file and I find no reference of the email address I am trying to send to. So I see the reference to the message in the message tracking log but not in the send log.
     

    That's a good thing. What are the events and sources you see?

    A:  RECEIVE  STOREDRIVER
         TRANSFER  ROUTING

     
    >If the message never makes it to the SEND/SMTP event then it's still
    in the categorizer.
     
    >For a message that's sent you should see this sequence of Event/Source
    in the message tracking log if everything's on the same machine:
     
    SUBMIT/STOREDRIV
    RECEIVE/STOREDRV
    TRANSFER/ROUTING
    SEND/SMTP
     
    A:  I do not know why the message is not being sent.  What now?  This is the only address we are having problems with.  All other messages are going out.  We have successfully sent to this email address.  This are no other addresses that we send to that particular name@company.com.

    Again thank you for helping me.   -tom




    • Edited by Poly Admin Wednesday, May 15, 2013 4:07 PM
    Wednesday, May 15, 2013 3:26 PM
  • On Wed, 15 May 2013 15:26:41 +0000, Poly Admin wrote:
     
    [ snip ]
     
    >>That's a good thing. What are the events and sources you see?
     
    >A: RECEIVE STOREDRIVER TRANSFER ROUTING
     
    >>If the message never makes it to the SEND/SMTP event then it's still in the categorizer.
     
    >>For a message that's sent you should see this sequence of Event/Source in the message tracking log if everything's on the same machine: SUBMIT/STOREDRIV RECEIVE/STOREDRV TRANSFER/ROUTING SEND/SMTP
     
    >A: I do not know why the message is not being sent. What now? This is the only address we are having problems with. All other messages are going out. We have successfully sent to this email address. This are no other addresses that we send to that particular name@company.com. Again thank you for helping me. -tom
     
    In that TRANSFER/ROUTING line, what's the value in the "SourceContext"
    column?
     
    In the "Routing" phase, after the "Next Hop" has been determined the
    message goes to the categorizer. The categorizer handles:
     
    1. Content Conversion
    2. Agent processing
    3. Message packaging
     
    You've seen the message enter the categorizer, and you say you see it
    in a queue -- but you never said which queue. I'm guessing it's not in
    a queue that has a domain name, but that's a guess. You can just look
    and see.
     
    If the message is failing content conversion it usually gets returned
    with a "content conversion failed" error. You can enable pipeline
    tracing to follow the message through the transport pipeline to see
    where it might be failing, or stalling).
     
    If the message is hung up in an agent (anti-virus, anti-spam,
    journaling, transport rule, etc.) the pileline tracing should help,
    too.
     
    If you run A/V or spam filters on the server you might want to check
    their log files for problems.
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    Thursday, May 16, 2013 1:31 AM
  • On Wed, 15 May 2013 15:26:41 +0000, Poly Admin wrote:
     
     
    >In that TRANSFER/ROUTING line, what's the value in the "SourceContext"

    column?

    A: ContentConversion

     
    >In the "Routing" phase, after the "Next Hop" has been determined the
    message goes to the categorizer. The categorizer handles:
     
    1. Content Conversion
    2. Agent processing
    3. Message packaging
     
    >You've seen the message enter the categorizer, and you say you see it
    in a queue -- but you never said which queue. I'm guessing it's not in
    a queue that has a domain name, but that's a guess. You can just look
    and see.

    A:  It does show a queue named: name@company.com and delivery type is DnsConnectorDelivery
     

    I appreciate your help.

    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP

    Thursday, May 16, 2013 3:12 PM
  • On Thu, 16 May 2013 15:12:23 +0000, Poly Admin wrote:
     
    >On Wed, 15 May 2013 15:26:41 +0000, Poly Admin wrote: >In that TRANSFER/ROUTING line, what's the value in the "SourceContext"
    >
    >column?
    >
    >A: ContentConversion >In the "Routing" phase, after the "Next Hop" has been determined the message goes to the categorizer. The categorizer handles: 1. Content Conversion 2. Agent processing 3. Message packaging >You've seen the message enter the categorizer, and you say you see it in a queue -- but you never said which queue. I'm guessing it's not in a queue that has a domain name, but that's a guess. You can just look and see. A: It does show a queue named: name@company.com and delivery type is DnsConnectorDelivery
    >
    >I appreciate your help.
     
    The queue should be named "company.com", not the entire email address.
    There would be a message in the queue that had the intended recipient
    address.
     
    Is there a "Last error" associated with the queue (or the whole e-mail
    address)?
     
    So, now we're down to a single domain, and perhaps a single e-mail
    address. What's the real e-mail address? Feel free to munge the
    address as long as it's understandable by a human. :-)
     
    I'm guessing there's a misspelling in the domain part of the address,
    or, if you used nslookup, that the domain name has no MX record and
    the "A" record for the domain resolves to the web site for the domain
    and not the SMTP MX for the domain.
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    Thursday, May 16, 2013 10:05 PM
  •  
    The queue should be named "company.com", not the entire email address.
    There would be a message in the queue that had the intended recipient

    address.
    A:  the queue name is company.com
    Sorry for the confusion.

    Is there a "Last error" associated with the queue (or the whole e-mail

    address)?
    A:  yes, the error is "451 4.4.0 primary target ip address responded with 421 4.4.2 connection dropped due to timeout...."

     
    So, now we're down to a single domain, and perhaps a single e-mail
    address. What's the real e-mail address? Feel free to munge the
    address as long as it's understandable by a human. :-)
    A:  the address is     m~t~r~a~m~m~e~l~l       < just remove the ~'s to unmunge :)
    at
    t a y l o r e n g i n e e r i n g . c o m

    I'm guessing there's a misspelling in the domain part of the address,
    or, if you used nslookup, that the domain name has no MX record and

    the "A" record for the domain resolves to the web site for the domain
    and not the SMTP MX for the domain.
     
    thanks - tom


    Monday, May 20, 2013 3:43 PM
  • On Mon, 20 May 2013 15:43:12 +0000, Poly Admin wrote:
     
    > The queue should be named "company.com", not the entire email address. There would be a message in the queue that had the intended recipient
    >
    >address. A: the queue name is company.com Sorry for the confusion. Is there a "Last error" associated with the queue (or the whole e-mail
    >
    >address)? A: yes, the error is "451 4.4.0 primary target ip address responded with 421 4.4.2 connection dropped due to timeout...." So, now we're down to a single domain, and perhaps a single e-mail address. What's the real e-mail address? Feel free to munge the address as long as it's understandable by a human. :-) A: the address is m~t~r~a~m~m~e~l~l < just remove the ~'s to unmunge :) at t a y l o r e n g i n e e r i n g . c o m
    >
    >I'm guessing there's a misspelling in the domain part of the address, or, if you used nslookup, that the domain name has no MX record and the "A" record for the domain resolves to the web site for the domain and not the SMTP MX for the domain. thanks - tom
     
    So what happens if you "telnet 50.203.116.74 25"? Do you get a 220
    SMTP banner? I do. And I get a 250 response when entering the RCPT TO
    address.
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    Tuesday, May 21, 2013 3:09 AM
  •  
    So what happens if you "telnet 50.203.116.74 25"? Do you get a 220
    SMTP banner? I do. And I get a 250 response when entering the RCPT TO
    address.

    A:  Funny thing.  The first time I tried it I just got a blinking cursor.  Then a few minutes later I tried it and I got the 220 smtp banner.  Several more tries worked fine as well.  Also a test email I sent to the address went thru late yesterday.  It seems to be an intermittent issue which is the worst kind.  I closed the command window then opened it back up to try telnet again.  It failed the first time again and just gave me a blinking cursor.  But a 2nd 3rd and 4th time it worked just fine.  It seems to fail the first attempt but work thereafter.  Very strange.

    I don't know if it is fixed or not.  I just sent another test msg and it went out too.  I haven't changed anything so I don't know why it is working now.  I will continue to monitor it.  I am interested to hear your thoughts.   thanks

     




    • Edited by Poly Admin Tuesday, May 21, 2013 6:47 PM
    Tuesday, May 21, 2013 2:51 PM
  • On Tue, 21 May 2013 14:51:03 +0000, Poly Admin wrote:
     
    > So what happens if you "telnet 50.203.116.74 25"? Do you get a 220 SMTP banner? I do. And I get a 250 response when entering the RCPT TO address.
    >
    >A: Funny thing. The first time I tried it I just got a blinking cursor. Then a few minutes later I tried it and I got the 220 smtp banner. Several more tries worked fine as well. Also a test email I sent to the address went thru late yesterday. It seems to be an intermittent issue which is the worst kind. I closed the command window then opened it back up to try telnet again. It failed the first time again and just gave me a blinking cursor. But a 2nd 3rd and 4th time it worked just fine. It seems to fail the first attempt but work thereafter. Very strange.
    >
    >I don't know if it is fixed or not. I just sent another test msg and it went out too. I haven't changed anything so I don't know why it is working now. I will continue to monitor it. I am interested to hear your thoughts. thanks
     
    That sure looks like a connectivity problem of some sort.
     
    You could try opening a 2nd command window and do "tracert
    50.203.116.74" while the 1st command window is sitting there with that
    blinking cursor. Does the packet eventually reach the target or does
    it start to time out somewhere along the way?
     
    Compare the hops to a tracert done while things are working. Are they
    different?
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    Wednesday, May 22, 2013 12:54 AM
  • The tracert completed successfully even with the 1st window sitting there with the blinking cursor.  Closed the 1st telnet window and opened up another and the telnet command got the 220 smtp banner perfectly.

    Thanks for your help.  It appears that my email system is working properly so I am not sure what else I can do.  Should we just close this issue and call it an anomaly?

    Wednesday, May 22, 2013 3:11 PM
  • On Wed, 22 May 2013 15:11:41 +0000, Poly Admin wrote:
     
    >
    >
    >The tracert completed successfully even with the 1st window sitting there with the blinking cursor. Closed the 1st telnet window and opened up another and the telnet command got the 220 smtp banner perfectly.
    >
    >Thanks for your help. It appears that my email system is working properly so I am not sure what else I can do. Should we just close this issue and call it an anomaly?
     
    Sure.
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    • Marked as answer by Poly Admin Thursday, May 23, 2013 1:30 PM
    Thursday, May 23, 2013 1:53 AM