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Can't send email to some external domains Exchange 2007

I am having issues sending emails to certain domains and other domains are fine.  I am getting these NDRs: #550 4.4.7 QUEUE.Expired; message expired ##.   I am currently running Windows SBS2008 with Exchange 2007 built in.  

Here is an output from get-queue |fl

Identity         : LASBS01\1590
DeliveryType     : DnsConnectorDelivery
NextHopDomain    : fbol.com
NextHopConnector : 12589173-ed78-4864-b6e1-d7426f68f803
Status           : Retry
MessageCount     : 1
LastError        : 451 4.4.0 Primary target IP address responded with: "554 mta
                   06.firstbanks-online.com." Attempted failover to alternate h
                   ost, but that did not succeed. Either there are no alternate
                    hosts, or delivery failed to all alternate hosts.
LastRetryTime    : 11/2/2008 3:54:51 PM
NextRetryTime    : 11/2/2008 4:04:51 PM
IsValid          : True
ObjectState      : Unchanged

Identity         : LASBS01\1969
DeliveryType     : DnsConnectorDelivery
NextHopDomain    : phs.com
NextHopConnector : 12589173-ed78-4864-b6e1-d7426f68f803
Status           : Retry
MessageCount     : 2
LastError        : 451 4.4.0 Primary target IP address responded with: "554 mai
                   l2.corpmailsvcs.com." Attempted failover to alternate host,
                   but that did not succeed. Either there are no alternate host
                   s, or delivery failed to all alternate hosts.
LastRetryTime    : 11/2/2008 3:53:42 PM
NextRetryTime    : 11/2/2008 4:03:46 PM
IsValid          : True
ObjectState      : Unchanged

Here is the output from get-sendconnector |fl
AddressSpaces                : {smtp:*;1}
AuthenticationCredential     :
Comment                      :
ConnectedDomains             : {}
ConnectionInactivityTimeOut  : 00:10:00
DNSRoutingEnabled            : True
DomainSecureEnabled          : False
Enabled                      : True
ForceHELO                    : False
Fqdn                         : mail.mydomain.com
HomeMTA                      : Microsoft MTA
HomeMtaServerId              : LASBS01
Identity                     : Windows SBS Internet Send LASBS01
IgnoreSTARTTLS               : False
IsScopedConnector            : False
IsSmtpConnector              : True
LinkedReceiveConnector       :
MaxMessageSize               : 10MB
Name                         : Windows SBS Internet Send LASBS01
Port                         : 25
ProtocolLoggingLevel         : None
RequireTLS                   : False
SmartHostAuthMechanism       : None
SmartHosts                   : {}
SmartHostsString             :
SourceIPAddress              : 0.0.0.0
SourceRoutingGroup           : Exchange Routing Group (DWBGZMFD01QNBJR)
SourceTransportServers       : {LASBS01}
UseExternalDNSServersEnabled : True
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Asked:
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1 Solution
 
Jerry SolomonNetwork  AdministratorCommented:
A 554 error usually means there is a problem you will need to address.  the first step is to determine what the response from the other mail server is.

The easiest way to do this is by opening a command prompt on your mail server to simulate an email connection.
1. perform the dns lookup for the other domain (probably not necessary here, but I would still do it to be thorough)
nslookup [enter]
set q=mx[enter]
recipientdomain.com[enter]
this will give you the mail server of the other domain.
exit[enter]
Now simulate a SMTP connection to see what the other server says.
telnet [mailservername] 25[enter]
helo [yourservername]
mail from:[youremail address][enter]
rcpt to:[recipientemailaddress][enter]
data[enter]
subject:test[enter]
This is atest message, please reply if you receive this[enter]
[enter]
.
[enter]
If you get a message queued for delivery, it all looks good, otherwise you will hopefully get some kind of error you can read in plain english which will give you good informatio on what to do next to resolve the issue.

good luck!
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pistolslapperCommented:
Looks to me like you have DNS problems. If you are sending mail directly from your SBS server you will need to masqerade your registered FQDN inside your exchange config. You will also need to make sure you have correctly setup a reverse DNS record for your domain. This is important because some mails server's filters perform reverse lookups on incoming mail and if the lookup fails the mail is dropped.

You may also be running into some mail servers that use greylisting. Greylisting is when a mailserver recieves a message from a domain it doesnt know and doesnt accept the mail. To get on the list of accepted domains you need to retry the send within 300 seconds (this is the figure i've seen a few times) then it will acept the mail and add you to the known list.

A couple of  good sites for testing your mail setup and dns are - http://www.mxtoolbox.com/ and http://www.checkdns.net

They will let you know if there are any issues and possible resolutions.


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UndisputedAuthor Commented:
Ok I'm not sure what happened but my problems may have been fixed.  I will keep this open just in case.  However, I didn't do anything really except create a srv record at my dns provider with my autodiscovery url.  I doubt this is what fixed the issue but my emails are no longer in queue.  I also sent more test emails to those servers and nothing got stuck in queue.
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UndisputedAuthor Commented:
Ok I guess it's not fixed.  I am getting the following:

Identity         : LASBS01\2967
DeliveryType     : DnsConnectorDelivery
NextHopDomain    : messaging.sprintpcs.com
NextHopConnector : 12589173-ed78-4864-b6e1-d7426f68f803
Status           : Retry
MessageCount     : 2
LastError        : 451 4.4.0 Primary target IP address responded with: "554 lxn
                   ipc6003.nmcc.sprintspectrum.com." Attempted failover to alte
                   rnate host, but that did not succeed. Either there are no al
                   ternate hosts, or delivery failed to all alternate hosts.
LastRetryTime    : 11/4/2008 12:33:53 PM
NextRetryTime    : 11/4/2008 12:43:54 PM
IsValid          : True
ObjectState      : Unchanged

Identity         : LASBS01\3503
DeliveryType     : DnsConnectorDelivery
NextHopDomain    : silkybottom.com
NextHopConnector : 12589173-ed78-4864-b6e1-d7426f68f803
Status           : Retry
MessageCount     : 1
LastError        : 451 4.4.0 Primary target IP address responded with: "421 4.2
                   .1 Unable to connect." Attempted failover to alternate host,
                    but that did not succeed. Either there are no alternate hos
                   ts, or delivery failed to all alternate hosts.
LastRetryTime    : 11/4/2008 12:33:51 PM
NextRetryTime    : 11/4/2008 12:44:12 PM
IsValid          : True
ObjectState      : Unchanged

Identity         : LASBS01\3509
DeliveryType     : MapiDelivery
NextHopDomain    : mail.mydomain.com
NextHopConnector : 00000000-0000-0000-0000-000000000000
Status           : Ready
MessageCount     : 0
LastError        :
LastRetryTime    : 11/4/2008 12:36:25 PM
NextRetryTime    :
IsValid          : True
ObjectState      : Unchanged

Identity         : LASBS01\3563
DeliveryType     : DnsConnectorDelivery
NextHopDomain    : yahoo.com
NextHopConnector : 12589173-ed78-4864-b6e1-d7426f68f803
Status           : Ready
MessageCount     : 0
LastError        :
LastRetryTime    : 11/4/2008 12:35:47 PM
NextRetryTime    :
IsValid          : True
ObjectState      : Unchanged

Identity         : LASBS01\3566
DeliveryType     : DnsConnectorDelivery
NextHopDomain    : mgm.com
NextHopConnector : 12589173-ed78-4864-b6e1-d7426f68f803
Status           : Ready
MessageCount     : 0
LastError        :
LastRetryTime    : 11/4/2008 12:37:05 PM
NextRetryTime    :
IsValid          : True
ObjectState      : Unchanged

Identity         : LASBS01\3567
DeliveryType     : DnsConnectorDelivery
NextHopDomain    : cirquedusoleil.com
NextHopConnector : 12589173-ed78-4864-b6e1-d7426f68f803
Status           : Ready
MessageCount     : 0
LastError        :
LastRetryTime    : 11/4/2008 12:37:28 PM
NextRetryTime    :
IsValid          : True
ObjectState      : Unchanged

Identity         : LASBS01\Submission
DeliveryType     : Undefined
NextHopDomain    : Submission
NextHopConnector : 00000000-0000-0000-0000-000000000000
Status           : Ready
MessageCount     : 0
LastError        :
LastRetryTime    :
NextRetryTime    :
IsValid          : True
ObjectState      : Unchanged
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pistolslapperCommented:
have you checked to see if your mailserver is blacklisted? check out www.mxtoolbox.com
- you will find a place where u can test your mail server.

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UndisputedAuthor Commented:
definitely not blacklisted.  reverse dns is configured correctly also.

Any other ideas?
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UndisputedAuthor Commented:
I notice when this stuff happens, I try to telnet into their mail server and the connection just drops right away.
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UndisputedAuthor Commented:
also, when i launch nslookup by right clicking on my sbs 2008 server name it shows a default server and IP.  However, if I try to run nslookup from just a command prompt it shows an unknown default server and what looks like a tcp/ip v6 address.
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UndisputedAuthor Commented:
fixed the v 6 issue so nslookup works properly now.  However, even when I try to telnet (from different ext IP addresses) to the domains that i'm having issues with, I keep getting error 554.
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Jerry SolomonNetwork  AdministratorCommented:
The most important part of that error 554 is the text that almost always accompanies it when you do the telnet test--What is the actual response? It is usually self-explanatory, and ofent even gives instructions on how to fix it.
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UndisputedAuthor Commented:
when i do the telnet test this is what i get:
     554 mail03.viacom.com
     Connection to host lost.

I get that response right when I type telnet mail1.viacom.com 25

When I ping mail1.viacom.com i get the correct ip: 166.77.11.50 but when I ping mail03.viacom.com I get 166.77.11.7
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UndisputedAuthor Commented:
I've done all dns tests and EVERYTHING is pointing to the fact that my setup is correct.  I'm just lost now.
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UndisputedAuthor Commented:
Ok i am not sure if this means anything but for some reason, whether inside my office network or on another network I cannot do the telnet test to mail1.viacom.com or any of the other domains I have issues with like fbol.com or phs.com.

People who are on xp pro or linux boxes can do the telnet test fine but vista and sbs 2008 boxes (w/exchange 2007) cannot.  Is there some command differences that are causing these immediate disconnect failures?  This may have some bearing on why I cannot send emails to those domains properly.

Can someone try and verify that they can or can't also?
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Jerry SolomonNetwork  AdministratorCommented:
Are you doing an mx lookup for thos domains so you connect to the correct server name?

centralops.net has an easy MX lookup gui.
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UndisputedAuthor Commented:
yes of course
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UndisputedAuthor Commented:
It was an issue on the other domain addresses I sent to.  They had to add me to their whitelists.
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