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Why mails to certain domains always stuck in queue in Exchange 2007

Posted on 2014-12-25
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Last Modified: 2015-01-22
This is using a single MS Exchange 2007 server. Recently, found that outgoing mails to a few domains always ended up in queue, and these mails eventually purged upon 2 days. On mxtoolbox, do not found that that the exchange Ip was blacklisted, and SMTP test passed. How should I troubleshoot and get this problem resolved? THe server os is w2k3 r2.

 Thanks in advance.
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Question by:MichaelBalack
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22 Comments
 
LVL 20

Expert Comment

by:SatyaPathak
ID: 40517545
if you are using any smarthost please remove it and then try it .
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LVL 20

Expert Comment

by:SatyaPathak
ID: 40517546
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LVL 35

Expert Comment

by:Kimputer
ID: 40517569
You troubleshoot by fungus out the exact reason why they're placed in the queue.
Either by checking the NDR message, or just watching the actually mail traffic conversion (using Wireshark).
After you know the reason, we can continue for the solution.
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LVL 76

Expert Comment

by:Alan Hardisty
ID: 40517995
Please have a read through my article and run through the various tests I've listed:

http://www.experts-exchange.com/Software/Server_Software/Email_Servers/A_2427-Problems-sending-mail-to-one-or-more-external-domains.html

If you don't find any good reasons, it may be that the recipient domains are blocking you and only direct contact with those domains via the phone / web may get the problem resolved.

Alan
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Author Comment

by:MichaelBalack
ID: 40518039
Hi Kimputer,

No ndr for those mails in queue.
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LVL 16

Expert Comment

by:Viral Rathod
ID: 40518206
Please do telnet to those domain ip address for which the e-mail is getting stuck and send e-mail using telnet utility and check which errors another domains gives , this will resolve your problems.

Send e-mail using telnet :-

nslookup
set q=mx
e-mail stuck domain name
this will give the ip adddress
do telnet on server ip address on 25 port
helo domain name
mail from:your domain name
mail to : receipient name
data test
.
Check for errors :-

Please free to revert in case of any issues.
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Expert Comment

by:Adam Farage
ID: 40519310
Get the error message that you see in queue please, shocked nobody asked for this:

Get-Queue | Get-Message | FL

Open in new window


Post it here (should be ran in Exchange Management Shell).. this can be a number of things such as "domain not found" or a network connectivity issue. Also what queue are these messages stuck in?
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Author Comment

by:MichaelBalack
ID: 40520350
Hi Adam,

Sorry for the delay.

I type the get-queue, and result show blank. Think those stuck mails die off after 2 days.
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LVL 1

Author Comment

by:MichaelBalack
ID: 40520351
Hi Viral,

So far, I know there are 4 domains in which mails headed would stuck. I'll type them 1-by-1 now...
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Expert Comment

by:Alan Hardisty
ID: 40520363
Any responses to the other experts trying to help you?
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Author Comment

by:MichaelBalack
ID: 40520432
Hi Viral,

Just want to check the commands:

Suppose the suspected domain name is abc.com, and the recipient address is recipientA@abc.com;
After telnet mail.abc.com 25, what are the commands I have to type in?

    - telnet mail.abc.com
    - helo abc.com  (get 250)
    - mail from:senderA@def.com (get 251 - sender ok)
    - mail to:recipientA@abc.com (get 551- domain required)

Please advise...
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Author Comment

by:MichaelBalack
ID: 40520439
Hi Viral,

After the mail from:. that should be "rcpt to:", right?
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Expert Comment

by:Alan Hardisty
ID: 40520446
Unsubscribed.
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LVL 35

Expert Comment

by:Kimputer
ID: 40521603
As I mentioned before, use Wireshark to get the whole conversation. The telnet works for simple things, but if you don't have the full conversation, sometimes you still miss the real cause (for instance some spam engine, that only activates according to the header, which you didn't mimic properly with that telnet session)
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LVL 19

Expert Comment

by:Adam Farage
ID: 40521795
WireShark is great but can be overly complex for a situation like this. If the message is actually "stuck in queue" running the powershell command above will give the SMTP code out for it. Messages should expire after 7 days, but I could also be wrong.

If we try to send a message to one of those domains please run the command I have above and see what the actual error is.. It is most likely not getting stuck in Exchange but a third party smarthost (e.g: spam filter)
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Author Comment

by:MichaelBalack
ID: 40523812
Hi all,

Some one suggested to create a new sendconnector, with forcehelo=$true.

I create one, and shortlisted those affected domains, and hurray, mails successfully sent. But why? some more is this one doesn't look like a problem resolution, isn't it?
0
 
LVL 19

Expert Comment

by:Adam Farage
ID: 40525023
I guess my main question is what was the old send connector setup as? Run Get-SendConnector | FL and post the output, I am sure you had something like "IPSec" checked off which may have threw it off..
0
 
LVL 1

Author Comment

by:MichaelBalack
ID: 40526413
Hi Adam,

Please see the results of "get-queue | get-message | fl"

get-queue | get-message | fl

Identity          : mail1\23389\4229
Subject           : RE: PACKING LIST NANYA PO 23060R1 + 23004
InternetMessageId : <2B5C14AF3AA2DB4EAB40EE384328D1CF011D89CA0FE6@mail1.cannon.
                    local>
FromAddress       : Stella@mycompany.com
Status            : Ready
Size              : 52237B
MessageSourceName : FromLocal
SourceIP          : 255.255.255.255
SCL               : -1
DateReceived      : 2014-12-30 16:52:36
ExpirationTime    : 2015-1-1 16:52:36
LastError         :
RetryCount        : 0
Queue             : mail1\23389
Recipients        :
IsValid           : True
ObjectState       : Unchanged

Identity          : mail1\23739\4322
Subject           : [Yoke] Piping direction and port connection, pls confirm
InternetMessageId : <2B5C14AF3AA2DB4EAB40EE384328D1CF011D89CA0FFD@mail1.cannon.
                    local>
FromAddress       : yeokl@mycompany.com
Status            : Ready
Size              : 6424750B
MessageSourceName : FromLocal
SourceIP          : 255.255.255.255
SCL               : -1
DateReceived      : 2014-12-30 17:55:03
ExpirationTime    : 2015-1-1 17:55:03
LastError         :
RetryCount        : 0
Queue             : mail1\23739
Recipients        :
IsValid           : True
ObjectState       : Unchanged

Identity          : mail1\23739\5255
Subject           : Auld Lang Syne,
InternetMessageId : <2B5C14AF3AA2DB4EAB40EE384328D1CF011D89CA1063@mail1.cannon.
                    local>
FromAddress       : chingkwl@mycompany.com
Status            : Ready
Size              : 15412B
MessageSourceName : FromLocal
SourceIP          : 255.255.255.255
SCL               : -1
DateReceived      : 2014-12-31 11:44:28
ExpirationTime    : 2015-1-2 11:44:28
LastError         :
RetryCount        : 0
Queue             : mail1\23739
Recipients        :
IsValid           : True
ObjectState       : Unchanged

Identity          : mail1\23891\5027
Subject           : 未读: 【发票】代开.请电:1353 3800 200, 陈会计 QQ: 2914 806 327
InternetMessageId : <2B5C14AF3AA2DB4EAB40EE384328D1CF011D89DA1D6C@mail1.cannon.
                    local>
FromAddress       : lilian@mycompany.com
Status            : Ready
Size              : 3094B
MessageSourceName : FromLocal
SourceIP          : 255.255.255.255
SCL               : -1
DateReceived      : 2014-12-31 9:14:08
ExpirationTime    : 2015-1-2 9:14:08
LastError         :
RetryCount        : 0
Queue             : mail1\23891
Recipients        :
IsValid           : True
ObjectState       : Unchanged

Identity          : mail1\23892\5014
Subject           : 未读: 专业代理《国税》 《地税》各类发瞟,点数低、价格优惠,电话:1368 2691 924 张小姐 详谈QQ:17
                    85979398
InternetMessageId : <2B5C14AF3AA2DB4EAB40EE384328D1CF011D89DA1D5F@mail1.cannon.
                    local>
FromAddress       : lilian@mycompany.com
Status            : Ready
Size              : 3236B
MessageSourceName : FromLocal
SourceIP          : 255.255.255.255
SCL               : -1
DateReceived      : 2014-12-31 9:14:07
ExpirationTime    : 2015-1-2 9:14:07
LastError         :
RetryCount        : 0
Queue             : mail1\23892
Recipients        :
IsValid           : True
ObjectState       : Unchanged
0
 
LVL 1

Author Comment

by:MichaelBalack
ID: 40526414
Hi Adam,

Please see the results of "get-sendconnector" for the old connector:



AddressSpaces                : {smtp:*;1}
AuthenticationCredential     :
Comment                      :
ConnectedDomains             : {}
ConnectionInactivityTimeOut  : 00:10:00
DNSRoutingEnabled            : True
DomainSecureEnabled          : False
Enabled                      : True
ForceHELO                    : False
Fqdn                         : mail.mycompany.com
HomeMTA                      : Microsoft MTA
HomeMtaServerId              : MAILSrv
Identity                     : internet mail
IgnoreSTARTTLS               : False
IsScopedConnector            : False
IsSmtpConnector              : True
LinkedReceiveConnector       :
MaxMessageSize               : 20MB
Name                         : internet mail
Port                         : 25
ProtocolLoggingLevel         : Verbose
RequireTLS                   : False
SmartHostAuthMechanism       : None
SmartHosts                   : {}
SmartHostsString             :
SourceIPAddress              : 0.0.0.0
SourceRoutingGroup           : Exchange Routing Group (DWBGZMFD01QNBJR)
SourceTransportServers       : {MAIL1}
UseExternalDNSServersEnabled : False
0
 
LVL 24

Accepted Solution

by:
VB ITS earned 500 total points
ID: 40549038
Some one suggested to create a new sendconnector, with forcehelo=$true.

I create one, and shortlisted those affected domains, and hurray, mails successfully sent. But why? some more is this one doesn't look like a problem resolution, isn't it?
Nope, this is the solution. The problem is that the receiving mail server expects a HELO response instead of the default EHELO, so instead of allowing the rest of the email to transmit it drops the email the moment it receives the default EHELO response.
0
 
LVL 1

Author Closing Comment

by:MichaelBalack
ID: 40564364
Yes, create a new send conductor with forcehelo=true solve my problem. thanks a lot
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