421 4.4.2 mtain-md02.r1000.mx.aol.com Error: Timeout Exceeded


  • Hey folks,

    I am a bit stumped as to what exactly is going on here.

    I'm running Exchange 2007 SP3. (We're due Update Rollup 2.) For the most part, the Exchange server hums along happily. We send mail via one Send Connector to Google Postini. 

    One user sends out an email to a number of users, perhaps 50 in total. (I can get a real number if necessary.) These message sit in queue on the Exchange server and eventually time-out. When I investigate the message, I see:

    421 4.4.2 mtain-md02.r1000.mx.aol.com Error: Timeout Exceeded

    The trouble is I see this error for _every email address in the list._ You can see what I mean here: http://i.imgur.com/rQt0G.jpg

    Who is reporting this? Postini? AOL? Why would it be AOL especially if barely 10% of the email recipients are at AOL? Also, you can see that at least _one_ mail did go out (although it actually bounced because the comcast.net address is invalid).

    The user has a bonafide distribution list created in his Outlook with actual, correctly formatted email addresses. Still it is possible that something in these addresses is messing up the works.

    If you saw this in YOUR Exchange server, what would you think? 


    In the meantime, I am going to contact Postini (if it's even possible) and break up the list that's not working to see if there's a bad email address causing problems.





    Thursday, March 24, 2011 7:01 PM

All replies

  • If I saw that error I would doubt that the Send Connector was configured correctly. If you are routing email out through Postini then you shouldn't even see the AOL MX record hosts in the error, because the Send Connector would send all email straight to Postini. No DNS lookups or anything, as that would be the smart host's job.


    Simon Butler, Exchange MVP
    Blog | Exchange Resources | In the UK? Hire Me.
    Thursday, March 24, 2011 7:09 PM
  • Well, yes, that's true. However, the packet captures don't show that. Plus, the queue shows one destination as type "SmartHostConnectorDelivery."

    And the packet captures only show traffic from me to one of the IPs in Postini's delivery range --

    I believe that Postini pulls any destination servers errors and pushes them back to Exchange. This would seem to bare out with the single bounce from Comcast. The error comes back FROM the Comcast server, even though the message transmitted through Postini.


    Thursday, March 24, 2011 8:52 PM



    Does the issue occur on certain user or each user when trying to send the message? Please replace another user and send out the message to check the result.


    I suspect the issue can occur by incorrect Send Connecter settings, message restriction or smart host settings. To troubleshoot the issue, please post the Send connector protocol log files here for research. The log file can be located from the following location: C:\Program Files\Microsoft\Exchange Server\V14TransportRoles\Logs\ProtocolLog\SmtpSend


    For more information, please refer to the link below:






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    Tuesday, March 29, 2011 3:17 AM
  • Novak,

    Here is an SMTPConnector Log that I have been passing around on Google's Postini forum and in communication with Google's Enterprise Support. Sensitive information has been edited.

    I have confirmed with Postini that the number of addresses is not the issue. (It's 42 address. To them that's very small.) 

    I realize that I can create another SMTP connection to handle mail to AOL.com (since, it seems, when I remove the AOL addresses from the BCC, the problem goes away), but doing direct DNS delivery like that brings other problems sometimes. We prefer smarthost delivery if we can do it.


    011-03-25T18:53:42.755Z,Postini Outbound,08CD75BF118F7970,0,,,*,,attempting to connect 2011-03-25T18:53:42.880Z,Postini Outbound,08CD75BF118F7970,1,,,+,,

    2011-03-25T18:53:43.020Z,Postini Outbound,08CD75BF118F7970,2,,,<,220 Postini ESMTP 106 y6_37_0c5 ready. CA Business and Professions Code Section 17538.45 forbids use of this system for unsolicited electronic mail advertisements., 2011-03-25T18:53:43.020Z,Postini Outbound,08CD75BF118F7970,3,,,>,EHLO mail.*****************.com, 2011-03-25T18:53:43.145Z,Postini Outbound,08CD75BF118F7970,4,,,<,250-Postini says hello back, 2011-03-25T18:53:43.145Z,Postini Outbound,08CD75BF118F7970,5,,,<,250-STARTTLS,

    2011-03-25T18:53:43.145Z,Postini Outbound,08CD75BF118F7970,6,,,<,250-8BITMIME,

    2011-03-25T18:53:43.145Z,Postini Outbound,08CD75BF118F7970,7,,,<,250 HELP, 2011-03-25T18:53:43.145Z,Postini Outbound,08CD75BF118F7970,8,,,>,STARTTLS,

    2011-03-25T18:53:43.238Z,Postini Outbound,08CD75BF118F7970,9,,,<,220 Go ahead, 2011-03-25T18:53:43.238Z,Postini Outbound,08CD75BF118F7970,10,,,*,,Sending certificate 2011-03-25T18:53:43.238Z,Postini Outbound,08CD75BF118F7970,11,,,*,"CN=mail.*****************.com, OU=Domain Control Validated, O=mail.*****************.com",Certificate subject 2011-03-25T18:53:43.238Z,Postini Outbound,08CD75BF118F7970,12,,,*,"SERIALNUMBER=********, CN=Go Daddy Secure Certification Authority, OU=http://certificates.godaddy.com/repository, O=""GoDaddy.com, Inc."", L=Scottsdale, S=Arizona, C=US",Certificate issuer name 2011-03-25T18:53:43.238Z,Postini Outbound,08CD75BF118F7970,13,,,*,***************,Certificate serial number 2011-03-25T18:53:43.238Z,Postini Outbound,08CD75BF118F7970,14,,,*,*********,Certificate thumbprint 2011-03-25T18:53:43.238Z,Postini Outbound,08CD75BF118F7970,15,,,*,mail.*****************.com;www.mail.*****************.com,Certificate alternate names 2011-03-25T18:53:43.597Z,Postini Outbound,08CD75BF118F7970,16,,,*,,Received certificate 2011-03-25T18:53:43.597Z,Postini Outbound,08CD75BF118F7970,17,,,*,**********************,Certificate thumbprint 2011-03-25T18:53:43.597Z,Postini Outbound,08CD75BF118F7970,18,,,>,EHLO mail.*****************.com, 2011-03-25T18:53:43.738Z,Postini Outbound,08CD75BF118F7970,19,,,<,250-Postini says hello back, 2011-03-25T18:53:43.738Z,Postini Outbound,08CD75BF118F7970,20,,,<,250-8BITMIME,

    2011-03-25T18:53:43.738Z,Postini Outbound,08CD75BF118F7970,21,,,<,250 HELP, 2011-03-25T18:53:43.738Z,Postini Outbound,08CD75BF118F7970,22,,,*,43973,sending message 2011-03-25T18:53:43.738Z,Postini Outbound,08CD75BF118F7970,23,,,>,MAIL FROM:<user@*****************.com>,

    2011-03-25T18:53:43.972Z,Postini Outbound,08CD75BF118F7970,24,,,<,250 Ok, 2011-03-25T18:53:43.972Z,Postini Outbound,08CD75BF118F7970,25,,,>,RCPT TO:<******@camaratamasonry.com>, 2011-03-25T18:53:44.705Z,Postini Outbound,08CD75BF118F7970,26,,,<,250 Ok, 2011-03-25T18:53:44.705Z,Postini Outbound,08CD75BF118F7970,27,,,>,RCPT TO:<******@aol.com>, 2011-03-25T18:53:45.454Z,Postini Outbound,08CD75BF118F7970,28,,,<,250 Ok, 2011-03-25T18:53:45.454Z,Postini Outbound,08CD75BF118F7970,29,,,>,RCPT TO:<*******comcast.net>, 2011-03-25T18:53:48.870Z,Postini Outbound,08CD75BF118F7970,30,,,<,550 5.1.1 <*******@comcast.net> Account not available, 2011-03-25T18:53:48.870Z,Postini Outbound,08CD75BF118F7970,31,,,>,RCPT TO:<********@yahoo.com>, 2011-03-25T18:53:49.728Z,Postini Outbound,08CD75BF118F7970,32,,,<,250 Ok, 2011-03-25T18:53:49.728Z,Postini Outbound,08CD75BF118F7970,33,,,>,RCPT TO:<***********@bmc.com>, 2011-03-25T18:53:50.040Z,Postini Outbound,08CD75BF118F7970,34,,,<,250 Ok, 2011-03-25T18:53:50.040Z,Postini Outbound,08CD75BF118F7970,35,,,>,RCPT TO:<*******@msn.com>, 2011-03-25T18:53:50.493Z,Postini Outbound,08CD75BF118F7970,36,,,<,250 Ok, 2011-03-25T18:53:50.493Z,Postini Outbound,08CD75BF118F7970,37,,,>,RCPT TO:<*******@aol.com>, 2011-03-25T18:53:50.727Z,Postini Outbound,08CD75BF118F7970,38,,,<,250 Ok, 2011-03-25T18:53:50.727Z,Postini Outbound,08CD75BF118F7970,39,,,>,RCPT TO:<***********@comcast.net>, 2011-03-25T18:53:50.976Z,Postini Outbound,08CD75BF118F7970,40,,,<,250 Ok, 2011-03-25T18:53:50.976Z,Postini Outbound,08CD75BF118F7970,41,,,>,RCPT TO:<**********@windstream.net>, 2011-03-25T18:53:51.819Z,Postini Outbound,08CD75BF118F7970,42,,,<,250 Ok, 2011-03-25T18:53:51.819Z,Postini Outbound,08CD75BF118F7970,43,,,>,RCPT TO:<*********@huntongrp.com>, 2011-03-25T18:54:22.318Z,Postini Outbound,08CD75BF118F7970,44,,,<,250 Ok, 2011-03-25T18:54:22.318Z,Postini Outbound,08CD75BF118F7970,45,,,>,RCPT TO:<*******@aol.com>, 2011-03-25T18:54:22.520Z,Postini Outbound,08CD75BF118F7970,46,,,<,421 4.4.2 mtain-me02.r1000.mx.aol.com Error: timeout exceeded, 2011-03-25T18:54:22.536Z,Postini Outbound,08CD75BF118F7970,47,,,>,QUIT,

    2011-03-25T18:54:23.176Z,Postini Outbound,08CD75BF118F7970,48,,,<,221 Catch you later, 2011-03-25T18:54:23.176Z,Postini Outbound,08CD75BF118F7970,49,,,-,,Local

    Tuesday, March 29, 2011 5:01 PM
  • First, I would like to confirm the following questions:


    1. Have you created additional SMTP connecter and send mail via DNS to the recipient directly?

    2. Can you send the message successfully if the AOL addresses lists at To or CC tab instead of BCC?


    I suspect the issue is caused if there is any restriction when sending message via BCC at Google part. Hence, please try to confirm whether there is such setting.




    Please remember to click “Mark as Answer” on the post that helps you, and to click “Unmark as Answer” if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.
    Thursday, March 31, 2011 8:42 AM
  • Hi Novak,


    In answer to your questions:

    1. No, I have not. I can do that and it's one of the workarounds I am considering.

    2. I have not tried that and am a little hesitant to because of the fact the addresses will be exposed to all recipients. I have, however, sent ALL the aol.com addresses in a single message (BCCed) and that works fine.

    I have been in communication with Google Enterprise Support and they do not feel it is an issue on their end. They have really look at the logs so I am inclined to think they're not being flippant. I happen to think that Google is keeping the connection to AOL.com open while it processes each BCC address serially. However, they have not confirmed or denied that. I am still talking with them.

    We are also considering moving the customer to another spam filter vendor (and a different smarthost). The unfortunate reality is that when you do not buy Postini through a reseller, support is difficult.

    Friday, April 1, 2011 10:06 PM
  • thecompu,


    We've been having similar issues with Postini recently, but we are experiencing the opposite.  We are on the receiving end, using Postini as our spam filter, and the sender (sending to a fairly large number of users) has tried both To and BCC with the list of our recipients.  They are seeing the same timeout error you pasted above.


    Have you heard anything back from Postini support?  I've yet to hear back from them on an incident I opened 2 weeks ago...


    We will likely follow Novak's suggestion #1 as a workaround.

    Tuesday, April 5, 2011 3:43 PM
  • ksaltz,

    I have been in communication with Postini, yes, but the response time is anywhere from 24-48 hours between responses. You may want to try emailing them directly at esupport@google.com. At least one person there seems to have taken more than a passing interest in my issue, although it's pretty clear that the support, in general, is fairly superficial. (For instance, as a helpful tip, the person at that address pointed me to THIS THREAD about my problem. Heh. He wouldn't be able to identify me by name necessarily, but it's pretty clear this thread doesn't lead to any particular answer.) This has been a sore point for awhile now. At one time, I had at least 12 clients on Postini and the spam filter was very, very good. However, as little issues have come up and I've not been able to get real support, I've had to move them to other providers. So far, I've not found anyone that really matches Postini's filter record. 

    (For what it's worth, you can get better support if you buy through a Postini Partner, but my experience has been that these partners can charge nearly 10x the price per mailbox you would get going direct through Postini. Plus, while I agree the Partners are generally more knowledgeable, it seems they don't have any particular hotline to Postini/Google engineers either. At least, I've not seen evidence of that.)

    I have gotten Postini to confirm that when a message is sent to multiple recipients when using Postini as a SmartHost, Postini makes direct, immediate connections to the destination mail servers during the session between my server and Postini. According to Postini if any message fails to go out, it should be reinjected into my server. In other words, if I send mail to 20 recipients and recipient 19 fails, Postini should re-inject into my server the mail bound ONLY for the 19th recipient. At a later time, my server will send the reinjected message. 

    But this is not happening. The initial message with 20 recipients (an example) is failing to go out. No reinjection attempt is made.

    Currently, I am trying to get Postini to answer this question for me: Should reinjection occur in this instance? It sounds like this scenario should be covered by reinjection. I haven't heard back yet, but that message was sent late yesterday.

    I'm very interested in the error you're seeing, but, on the surface, it really doesn't seem like the same thing. One of Postini's mail servers could indeed be timing out in your case, but my error is actually coming from an AOL mailserver whose communication is delivered back to me through my connection to the Postini Smarthost.

    Still post any logs if you have them. Just scrub them of potential identifying data!

    Tuesday, April 5, 2011 4:35 PM
  • thecompu,

    I appreciate your quick and thorough response.  I resolved the issue by simply bypassing Postini (fortunately I have access to Exchange on both ends).  On the recipient Exchange server, I was not seeing any connection attempt through Postini matching the recipient list I was expecting.  In my case, it appears the timeout was happening at the Postini level.  I'll open a ticket with them and will be sure to update this thread if I make any progress.

    Thanks again

    Tuesday, April 5, 2011 5:10 PM