Could not deliver the message in the time limit specified

Dear all,
       One of my client try to send out a email, but the email bounce back, what's the primary step we should troubleshoot this problem?  How to resolve?

Your message did not reach some or all of the intended recipients.

      Subject:      RE: DBA701 - Urgent
      Sent:      4/13/2004 5:39 PM

The following recipient(s) could not be reached:

      '' on 4/15/2004 6:00 PM
            Could not deliver the message in the time limit specified.  Please retry or contact your administrator.

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GearyTechConnect With a Mentor Commented:
      4.4.7   Delivery time expired

          The message was considered too old by the rejecting system,
          either because it remained on that host too long or because
          the time-to-live value specified by the sender of the
          message was exceeded. If possible, the code for the actual
          problem found when delivery was attempted should be returned
          rather than this code.  This is useful only as a persistent
          transient error.

Or, in English, you sent a message to a mail server that wasn't responding. Messages are typically held for 4 days and retried at regular intervals. After the 4 days, the message is returned to you. The problem is not at your end... it's at the recipient's end.

Troubleshooting email is fairly easy by using the returned error code. In this case, it was a code of 4.4.7.  These error codes can be referenced in the rfc1893 document at:  - not necessarily the easiest document to read... but an excellent reference to get you going down the right road.

Good luck.
MeteorGardenAuthor Commented:
It's funny. I can send out from Hotmail email account and get reply from the user.

I'm not sure what happening in my server. As from your reply, this is the recipient's error, but receipient receive it, how do i solve it from my server????

Thank you.

Support document from Symantec on how to troubleshoot SMTP connections.

Manually connecting might give you a better description on why your client is unable to send to this address. Your client may be on a blocklist.

Check his IP address here.

If you do manually connect to the SMTP server and need more help, cut and paste your session....

Free Tool: IP Lookup

Get more info about an IP address or domain name, such as organization, abuse contacts and geolocation.

One of a set of tools we are providing to everyone as a way of saying thank you for being a part of the community.

This happens to me from my work to my home server because my work server performs reverse dns before delivery.  The "symptom" of the reverse dns failing is that the mail never gets delivered and eventually times out.  Unfortunately, since my IP is dynamic and I don't own it, I cannot setup reverse DNS.
I have this same issue with a particular address. We can send from home but not from our exchange server. Can you tell mw what actually solved your problem

   We have an Exchnge Server 2003 installed in our organization.With the
latest service pack 1.our mails were working fine till last week.Now it is
not delivering messages to some of the domains
(,, which were working fine before.
I tried to send some test messages but we got the error as show bellow.
Your message did not reach some or all of the intended recipients.

      Subject:      lobdan for trainning      Sent:      6/27/2005 2:57 PM

The following recipient(s) could not be reached:

      denna loblan  on 6/27/2005 5:06 PM
            Could not deliver the message in the time limit specified.  
Please retry or contact your administrator.
            <icexsrvr.INFOCALL.COM #4.4.7>
Is there any resollution forthis problem.

Goto and do a reverse DNS lookup for your public IP and see if there is a PTR.  IF there is not, it is possible that some ISP (like AOL) will reject your email.

Steve G
We are getting this NDR 4.4.7 undeliverable email issue as well.  see below:


Your message did not reach some or all of the intended recipients.

      Subject:      RE: subject
      Sent:      10/18/2007 9:12 AM

The following recipient(s) could not be reached: on 10/20/2007 9:24 AM
            Could not deliver the message in the time limit specified.  Please retry or contact your administrator.
            < #4.4.7>


I've already contacted our reverse DNS provider and had them change our entry from "" to "".  that didn't work.

any suggestions?  we need help!  this only happens with a few domains ... all the time with new emails or replies.  thanks!
We just switched ISP's and had the same error message.  First thing we did to fix it was make sure our Reverse DNS was moved over to the new IP issues by the ISP.  

Second thing that needed to be done was to go into the following:

Exchange System Manager -> Administrative Groups -> First Administrative Group -> Routing Groups -> Your Routing Group -> Connectors -> SMTP Virtual Connector

Go into the properties of the SMTP Virtual Connector and on the 'Address Space' tab make sure that the 'Allow messages to be relayed to these domains' is unchecked.

If you are still having issues, set up another Virtual SMTP connector and use your ISP's mail server to relay the messages for problem domains.  I've done this too in the past and have had no issues.

Hope this helps
This was resolved with the help of Microsoft Professional Support.

Here's the jist of our solution:

Microsoft found that our DNS servers were missing the forwarder addresses and also our Cisco ASA firewall was blocking ESMTP traffic (via article 295725).  

After these two major things were found and fixed, we went through the remaining domains that were still would not process through in the queue and found that a good 80-90% were using/connected to Road Runner.  Telneting into Road Runners mail servers gave us a detailed error message that we used to find that our mail servers IP address is on Road Runners blacklist and therefore rejecting us.  I went to Road Runners page they gave to request removal from their blacklist.
This could very well be caused by the recipients server using a greylist ...

Below are the steps to overcome this issue. You must add a GlitchRetrySeconds to the Exchange server Registry

To configure the glitch retry interval in Exchange Server 2003
Open a registry editor, such as Regedit.exe or Regedt32.exe.

Navigate to: HKLM\System\CurrentControlSet\Services\SMTPSvc.

Right-click SMTPSvc and select New | Key.

Name the new key Queuing.

Right-click Queuing and select New | DWORD Value.

Name the new DWORD value .

Double-click GlitchRetrySeconds to edit its value data.

Change the Base to Decimal

In the Value data field, enter the number of seconds (60) that Exchange Server 2003 should wait before attempting to resend a message.

Click OK to save the change, and then close the Registry Editor.

Restart the Simple Mail Transfer Protocol (SMTP) service for the change to take effect.

Write a script that restarts the SMTP service nightly. (smtp.bat)

net stop smtpsvc
net start smtmsvc

Use Task Scheduler to schedule this file run.
What is the purpose of writing the smtp.bat file?

Any comments would be appreciated

The reason for are email error delay:
Could not deliver the message in the time limit specified. Please retry or contact your administrator.
< #4.4.7>
 Due to email was going out a different public IP and was coming in another IP. By the NAT's setup on the firewall. Since there was not PTR for the out going IP.
In our scenario, only when user sends an UPDATING meeting request (including cancellation), he/she may receive the NDR message.
This happens when an Exchange 2007 user accepts a meeting request from an Exchange 2003 user, the X-MICROSOFT-CDO-ATTENDEE-CRITICAL-CHANGE attribute is missed. In the Outlook 2007 client, if the X-MICROSOFT-CDO-ATTENDEE- CRITICAL-CHANGE attribute is missing, the PR_RECIPIENT_TRACKSTATUS_TIME property is set to "1/1/1601 00:00:00 AM." When the Exchange 2003 user tries to send an update of the meeting request or a cancellation of the meeting request, the value of the PR_RECIPIENT_TRACKSTATUS_TIME property cannot be successfully converted from the MAPI format to the MIME format by using the VariantTimeToSystemTime function, thus giving the NDR message.
Microsoft issued a hotfix for this issue.  Refer to to apply the patch.
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