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'421 4.4.1 connection timed out' error on some outgoing email in Exchange 2007

Posted on 2012-08-28
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Last Modified: 2012-11-12
I have a customer who has a strange issue with the mentioned error on roughly 2-3% of outgoing email.  Its exchange 2007 and I am using Symantec Mail Security (SMSME v6).  I'm not getting other application errors in the eventlog.  Everything is running fine.

Have checked mxtoolbox and they are on no RBL's which was my first thought.  Has anyone come across this?
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Question by:gambit120
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16 Comments
 
LVL 52

Expert Comment

by:Manpreet SIngh Khatra
ID: 38344227
It could be some other problems with their firewall i guess .... there is no issues at your end.

- Rancy
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LVL 8

Expert Comment

by:S_K_S
ID: 38344348
Are the outgoing emails going to any specific domain. Why not checking through http://testexchangeconnectivity.com/

Regards
SKS
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Author Comment

by:gambit120
ID: 38344365
the sender id validation came back with:

"Attempting to find the SPF record using a DNS TEXT record query.
  ExRCA wasn't able to find the SPF record."

Test was successful with the above as a warning on the last step.
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LVL 18

Expert Comment

by:Sushil Sonawane
ID: 38344426
Disable the Symantec Mail Security (SMSME v6) and try to resend the mail.
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LVL 52

Expert Comment

by:Manpreet SIngh Khatra
ID: 38344803
Hope you ahve Exclusions for SMSME not to scan Exchange files ?

- Rancy
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LVL 6

Expert Comment

by:jennylembert
ID: 38344820
You might want to have a look at this discussion for more info:
http://www.petri.co.il/forums/showthread.php?t=42478
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Author Comment

by:gambit120
ID: 38348088
Disabling SMSME and trying the test ended up with the same result.  Rancy what files should SMSME not be scanning?
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LVL 52

Expert Comment

by:Manpreet SIngh Khatra
ID: 38349803
Exchange Database ..... Microsoft folder and setup files.

http://support.microsoft.com/kb/323664

- Rancy
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Author Comment

by:gambit120
ID: 38352517
Rancy that has already been done.
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LVL 8

Expert Comment

by:S_K_S
ID: 38352743
Well do you mind updating us if the problem is with the outgoing emails going to any specific domain or is it any domain. Are you able to send out at all?
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Author Comment

by:gambit120
ID: 38352769
its only a small percentage of email outgoing to certain domains.  Everything else is working.  I am going to create an SPF record to see if that changes anything.
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LVL 8

Expert Comment

by:S_K_S
ID: 38352794
Had to ask that question I put up on the last note as I didnot want to simply jump onto giving vague suggestions. now that my question is answered and the error you shared from testexchangeconnectivity.com it makes sense working on your SPF records.

http://efreedom.com/Question/2-326996/Exchange-Failing-Outbound-Smtp-Test

Kindly keep us updated on how things go and in case of any query feel free to ask.

Regards,
SKS
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LVL 18

Expert Comment

by:Sushil Sonawane
ID: 38352797
SPF record will be help you and it's better for your mail domain.
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LVL 52

Expert Comment

by:Manpreet SIngh Khatra
ID: 38353176
You need to understand what the issue is as if the issue isnt related to SPF then not sure how it will help this cause ?
Anyways if you are trying and done let us know what happens for us to be able to check more things if it doesnt resolves.

- Rancy
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LVL 33

Accepted Solution

by:
Exchange_Geek earned 1500 total points
ID: 38441030
Understand, SPF Record is not going to help you. If you had SPF Failures, you would have seen NDR Code "#5.7.1 smtp;550 5.7.1 Rejected due to SPF policy for sender"

Hence, your issue is purely network -
=> it could be network issue to reach out the MX Record of the recipient domain
=> it could be issue where recipient domain couldn't send SMTP hand-shake response to your domain.

Too many causes.

What can be a conclusive solution is to find out if repeatedly you are unable to send emails to a particular domain? if yes, try sending from external domains - say gmail.com / hotmail.com etc. If it works externally - you should try creating a SMTP connector and point to MX Record by adding the IP as smart host.

If this doesn't work, get your network folks involved and have them review firewall logs.

That's your step by step solution for this issue.

Regards,
Exchange_Geek
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Author Closing Comment

by:gambit120
ID: 38593066
Was only certain domains that rejected email consistently. But will try what you said.
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