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

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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MichaelBalackAsked:
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Satya PathakLead Technical ConsultantCommented:
if you are using any smarthost please remove it and then try it .
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Satya PathakLead Technical ConsultantCommented:
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KimputerCommented:
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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Alan HardistyCo-OwnerCommented:
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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MichaelBalackAuthor Commented:
Hi Kimputer,

No ndr for those mails in queue.
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Viral RathodConsultantCommented:
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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Adam FarageEnterprise ArchCommented:
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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MichaelBalackAuthor Commented:
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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MichaelBalackAuthor Commented:
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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Alan HardistyCo-OwnerCommented:
Any responses to the other experts trying to help you?
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MichaelBalackAuthor Commented:
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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MichaelBalackAuthor Commented:
Hi Viral,

After the mail from:. that should be "rcpt to:", right?
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Alan HardistyCo-OwnerCommented:
Unsubscribed.
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KimputerCommented:
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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Adam FarageEnterprise ArchCommented:
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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MichaelBalackAuthor Commented:
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?
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Adam FarageEnterprise ArchCommented:
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..
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MichaelBalackAuthor Commented:
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
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MichaelBalackAuthor Commented:
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
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VB ITSSpecialist ConsultantCommented:
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.
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MichaelBalackAuthor Commented:
Yes, create a new send conductor with forcehelo=true solve my problem. thanks a lot
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