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421 4.4.2 Connection Dropped - Sending Mail with Attachments to Yahoo

    Question

  • Hi, have looked high and low for this today, will be getting in touch with Yahoo but thought someone else may have an idea on this!

    We are finding exchange servers from different clients are all having trouble sending large (varying from 4 to 10MB) emails to Yahoo. The size differs from site to site, some can send 4MB but not 10, other can't even send 4MB, but the symptoms are all the same... any small, text only emails send very quickly without issue... in the exchange queue viewer it says "Last Error: 421 4.4.2 Connection Dropped" and the SMTP Logs look like the below... basically the mail server contacts Yahoo, mailfrom/rcpt to standard stuff, yahoo gives the go ahead for data transfer (sequence number 14) then a few minutes later there is an '-' event, the context says 'remote', it all looks like it dropped (sequence event 15) and then the process starts again with a different yahoo MX. This has been going on for hours and hours!

    Any ideas would be greatly appreciated, I wondered if it might be something incorrect in our exchange config? We can send/receive mail to anyone else, with/without attachments of varying sizes... just sending to yahoo with largish attachments and it seems to bomb out...

    When I look at the performance monitor the network traffic being sent to yahoo's MX is pretty high, we noticed incoming mail didn't seem to be working... i suspended the mail in the queue going to yahoo and shortly after all the expected mail flowed in, not sure why they would have been affecting each other?

    This is Exch 2007 on 2008 R2. I tried disabling autotuning on one of the sites but it didn't seem to resolve the issue :-(.

    Thank you!

     

    #Fields: date-time sequence-number local-endpoint remote-endpoint event data context
    2011-03-04T04:36:38.991Z 0   74.6.136.244:25 *   attempting to connect
    2011-03-04T04:36:39.211Z 1 10.1.1.200:29218 74.6.136.244:25 +    
    2011-03-04T04:36:39.542Z 2 10.1.1.200:29218 74.6.136.244:25 < 220 mta1240.mail.sk1.yahoo.com ESMTP YSmtp service ready  
    2011-03-04T04:36:39.542Z 3 10.1.1.200:29218 74.6.136.244:25 > EHLO <REMOVED>  
    2011-03-04T04:36:39.762Z 4 10.1.1.200:29218 74.6.136.244:25 < 250-mta1240.mail.sk1.yahoo.com  
    2011-03-04T04:36:39.762Z 5 10.1.1.200:29218 74.6.136.244:25 < 250-8BITMIME  
    2011-03-04T04:36:39.762Z 6 10.1.1.200:29218 74.6.136.244:25 < 250-SIZE 41943040  
    2011-03-04T04:36:39.762Z 7 10.1.1.200:29218 74.6.136.244:25 < 250 PIPELINING  
    2011-03-04T04:36:39.763Z 8 10.1.1.200:29218 74.6.136.244:25 * 2422 sending message
    2011-03-04T04:36:39.763Z 9 10.1.1.200:29218 74.6.136.244:25 > MAIL FROM:<<REMOVED>> SIZE=12811187  
    2011-03-04T04:36:39.763Z 10 10.1.1.200:29218 74.6.136.244:25 > RCPT TO:<<REMOVED>@yahoo.com.au>  
    2011-03-04T04:36:39.998Z 11 10.1.1.200:29218 74.6.136.244:25 < 250 sender <<REMOVED>> ok  
    2011-03-04T04:36:40.416Z 12 10.1.1.200:29218 74.6.136.244:25 < 250 recipient <<REMOVED>@yahoo.com.au> ok  
    2011-03-04T04:36:40.642Z 13 10.1.1.200:29218 74.6.136.244:25 > DATA  
    2011-03-04T04:36:40.862Z 14 10.1.1.200:29218 74.6.136.244:25 < 354 go ahead  
    2011-03-04T04:42:13.266Z 15 10.1.1.200:29218 74.6.136.244:25 -   Remote
    2011-03-04T04:42:13.272Z 0   98.137.54.238:25 *   attempting to connect
    2011-03-04T04:42:13.490Z 1 10.1.1.200:29241 98.137.54.238:25 +    
    2011-03-04T04:42:13.766Z 2 10.1.1.200:29241 98.137.54.238:25 < 220 mta1060.mail.sp2.yahoo.com ESMTP YSmtp service ready  
    2011-03-04T04:42:13.769Z 3 10.1.1.200:29241 98.137.54.238:25 > EHLO <REMOVED>  
    2011-03-04T04:42:13.987Z 4 10.1.1.200:29241 98.137.54.238:25 < 250-mta1060.mail.sp2.yahoo.com  
    2011-03-04T04:42:13.987Z 5 10.1.1.200:29241 98.137.54.238:25 < 250-8BITMIME  
    2011-03-04T04:42:13.987Z 6 10.1.1.200:29241 98.137.54.238:25 < 250-SIZE 41943040  
    2011-03-04T04:42:13.987Z 7 10.1.1.200:29241 98.137.54.238:25 < 250 PIPELINING  
    2011-03-04T04:42:13.987Z 8 10.1.1.200:29241 98.137.54.238:25 * 2422 sending message
    2011-03-04T04:42:13.987Z 9 10.1.1.200:29241 98.137.54.238:25 > MAIL FROM:<<REMOVED>> SIZE=12811187  
    2011-03-04T04:42:13.987Z 10 10.1.1.200:29241 98.137.54.238:25 > RCPT TO:<<REMOVED>@yahoo.com.au>  
    2011-03-04T04:42:14.244Z 11 10.1.1.200:29241 98.137.54.238:25 < 250 sender <<REMOVED>> ok  
    2011-03-04T04:42:14.656Z 12 10.1.1.200:29241 98.137.54.238:25 < 250 recipient <<REMOVED>@yahoo.com.au> ok  
    2011-03-04T04:42:14.889Z 13 10.1.1.200:29241 98.137.54.238:25 > DATA  
    2011-03-04T04:42:15.107Z 14 10.1.1.200:29241 98.137.54.238:25 < 354 go ahead  
    2011-03-04T04:47:29.330Z 15 10.1.1.200:29241 98.137.54.238:25 -   Remote
    2011-03-04T04:47:29.331Z 0   74.6.140.64:25 *   attempting to connect

     

    Friday, March 04, 2011 6:28 AM

Answers

  • On Fri, 4 Mar 2011 06:28:24 +0000, Modular IT wrote:
     
    >Hi, have looked high and low for this today, will be getting in touch with Yahoo but thought someone else may have an idea on this!
    >
    >We are finding exchange servers from different clients are all having trouble sending large (varying from 4 to 10MB) emails to Yahoo. The size differs from site to site, some can send 4MB but not 10, other can't even send 4MB, but the symptoms are all the same... any small, text only emails send very quickly without issue... in the exchange queue viewer it says "Last Error: 421 4.4.2 Connection Dropped" and the SMTP Logs look like the below... basically the mail server contacts Yahoo, mailfrom/rcpt to standard stuff, yahoo gives the go ahead for data transfer (sequence number 14) then a few minutes later there is an '-' event, the context says 'remote', it all looks like it dropped (sequence event 15) and then the process starts again with a different yahoo MX. This has been going on for hours and hours!
    >
    >Any ideas would be greatly appreciated, I wondered if it might be something incorrect in our exchange config? We can send/receive mail to anyone else, with/without attachments of varying sizes... just sending to yahoo with largish attachments and it seems to bomb out...
     
    From the Exchange server that's sending the e-mail to Yahoo, try this:
     
    ping 74.6.136.244 -l 1472 -f
     
    Does that work? If not, there's a network device between you ans Yahoo
    that's either adding data to your packet or has a MTU smaller than
    yours. Keep reducing the 1472 until you can ping the target withug
    getting fragmentation errors. Then set your server's MTU accordingly
    on on the NIC that's being used to connect to Yahoo.
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    • Marked as answer by Frank.Wang Friday, March 11, 2011 1:32 AM
    Saturday, March 05, 2011 1:19 AM

All replies

  • On Fri, 4 Mar 2011 06:28:24 +0000, Modular IT wrote:
     
    >Hi, have looked high and low for this today, will be getting in touch with Yahoo but thought someone else may have an idea on this!
    >
    >We are finding exchange servers from different clients are all having trouble sending large (varying from 4 to 10MB) emails to Yahoo. The size differs from site to site, some can send 4MB but not 10, other can't even send 4MB, but the symptoms are all the same... any small, text only emails send very quickly without issue... in the exchange queue viewer it says "Last Error: 421 4.4.2 Connection Dropped" and the SMTP Logs look like the below... basically the mail server contacts Yahoo, mailfrom/rcpt to standard stuff, yahoo gives the go ahead for data transfer (sequence number 14) then a few minutes later there is an '-' event, the context says 'remote', it all looks like it dropped (sequence event 15) and then the process starts again with a different yahoo MX. This has been going on for hours and hours!
    >
    >Any ideas would be greatly appreciated, I wondered if it might be something incorrect in our exchange config? We can send/receive mail to anyone else, with/without attachments of varying sizes... just sending to yahoo with largish attachments and it seems to bomb out...
     
    From the Exchange server that's sending the e-mail to Yahoo, try this:
     
    ping 74.6.136.244 -l 1472 -f
     
    Does that work? If not, there's a network device between you ans Yahoo
    that's either adding data to your packet or has a MTU smaller than
    yours. Keep reducing the 1472 until you can ping the target withug
    getting fragmentation errors. Then set your server's MTU accordingly
    on on the NIC that's being used to connect to Yahoo.
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    • Marked as answer by Frank.Wang Friday, March 11, 2011 1:32 AM
    Saturday, March 05, 2011 1:19 AM
  • Hi Modular IT,

    Any updates?

    Please also check whether there is any error event in the Event Viewer.

    Frank Wang

    TechNet Subscriber Support in forum

    If you have any feedback on our support, please contact tngfb@microsoft.com  

     


    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.
    Monday, March 07, 2011 5:52 AM
  • Hi Frank,

    I have this same issue with Exchange 2010 setup.

    If I send 6MB email to yahoo, it's stuck in queue with "421 4.4.2 Connection dropped due to SocketError".

    But the same message I can sent to Gmail account without any errors.

    How can I change the MTU in Server 2008 R2?

    Thanks,

    Damitha

    Tuesday, April 12, 2011 4:03 PM
  • Dera all,

     

    Any update for this problem ?

    I have the same error

    I changed MTU in registry to 1472 but i still problem

    http://doitfixit.com/index.php?option=com_content&view=article&id=78:yahoo-emails421-442socketerror&catid=34:exchange-2010

     

    Please help.

     

    Thank you

    Phi,

     

     

    Tuesday, July 12, 2011 10:16 AM
  • Pleas help. It's urgent!

    Thank you,

    Phi,

    Wednesday, July 13, 2011 1:46 AM
  • Are there any new information about that problem?

    I have the same behaviour with an Exchange Server 2010 with multiple recipient mail systems. I have already changed the MTU size down to 1300, but nothing happens.

    Each time I decrease the MTU size, the connection drops happens again and the ping answers won't go through...

    Wednesday, September 14, 2011 6:37 AM
  • We were having similar errors showing up in our Exchange 2010 Queue Viewer.  Most e-mails were being delivered but a couple weren't.  The problem turned out to be on the Client's Firewall.  They were blocking any attachments with the word LIFE in the file name.  They were using a Watchguard Firewall.  The issue you are having with yahoo is that they only accept a 5 mb sized e-mail.  So instead of sending a reply back to the Exchange Server it leaves it hanging with the 421.4.4.2 error.

    Anyone know how to stop these from clogging up the Exchange Queues? 

    Wednesday, November 09, 2011 7:49 PM
  • On Wed, 9 Nov 2011 19:49:07 +0000, Jerry_R wrote:
     
    >
    >
    >We were having similar errors showing up in our Exchange 2010 Queue Viewer. Most e-mails were being delivered but a couple weren't. The problem turned out to be on the Client's Firewall. They were blocking any attachments with the word LIFE in the file name. They were using a Watchguard Firewall. The issue you are having with yahoo is that they only accept a 5 mb sized e-mail. So instead of sending a reply back to the Exchange Server it leaves it hanging with the 421.4.4.2 error.
    >
    >Anyone know how to stop these from clogging up the Exchange Queues?
     
    Try creating another send connector for yahoo.com and limit the
    message size to 5MB?
     
    What you're asking for, otherwise, is how to not keep retrying on
    transient errors for so long. That's managed with the
    set-transportserver's "-MessageExpirationTimeout" parameter.
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    Wednesday, November 09, 2011 10:08 PM