Exchange SMTP won't deliver outbound mail; I give up

Posted on 2005-03-10
Medium Priority
Last Modified: 2008-01-16
I've exhausted every web resource on this. Installed E2k server in 5.5 site, moved a couple mailboxes. Everything about the setup works now (after a week of troubleshooting other problems) except for the outbound mail. Inbound works fine, within org works fine, outbound no dice. There's nothing in the queues, message tracking will not find them, they just sit somewhere I guess, until I turn the IMS from 5.5 back on, then they go out. It could well be they sit in the 5.5 server but why and how would I stop that? DNS configured correctly.

Let me show the current settings for the default SMTP virtual server:
IP address: all unassigned (port 25)
Logging enabled
Access: Anonymous, Basic, and Integrated
Relay: only list below (blank); allow all computers which authenticate .... (also tried with this off, doesn't work either way)
Default Message settings
Delivery: default, anonymous access
Advanced Delivery: 15
masquerade: mydomain.com
fqdn: mail.mydomain.com or actual internal fqdn which is mx1.hq.mydomain.com; tried both of them.
no smart host.
no reverse DNS.
external DNS servers configured for internet DNS servers, not my internals at hq.mydomain.com that I tried also.

Somebody please help me figure this out!

Question by:Winstink
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LVL 27

Accepted Solution

Exchange_Admin earned 2000 total points
ID: 13512172
This happens because when an Exchange 2000 server is added to an Exchange 5.5 site, it will use the IMS on the 5.5 server to send out email.

Look at this:
To reroute incoming Internet e-mail to the Exchange 2000 Server computer
To reroute incoming e-mail, use one of the following methods:• If you have a firewall that routes e-mail messages to a private IP address on your Exchange Server 5.5 computer, you can reconfigure your firewall to route e-mail messages to the private IP address of the Exchange 2000 Server computer.
• Swap IP addresses of the new Exchange 2000 Server computer and the old Exchange Server 5.5 computer. Note that this can result in some temporary name resolution issues on your network. After changing the IP address of the Exchange 2000 server you will need to update its records in DNS and AD. To do this, go to a command prompt, you must run the following commands:• IPCONFIG /FLUSHDNS

Then restart the NET LOGON service on the Exchange 2000 Server computer, and then restart the Exchange Server 5.5 computer.
• Alternatively, have your Internet Service Provider (ISP) update the mail exchange (MX) record to reference the new Exchange 2000 Server computer. You can expect incoming e-mail to be disrupted for at least three hours, and up to three days, while this update is replicated over the Internet.
Note If there is no SMTP connector on the computer that is running Exchange 2000 Server, mail cannot leave the site if you disable the Internet Mail Service (IMS). Because of this, you must create an SMTP connector on the computer that is running Exchange 2000 Server before you remove the Exchange Server 5.5 IMS.

back to the top
To reroute outgoing Internet e-mail through the Exchange 2000 Server computer
1. Configure a new SMTP connector on the Exchange server that you want to be the bridgehead server for outgoing Internet mail. For additional information, click the following article number to view the article in the Microsoft Knowledge Base:
265293 How to configure the SMTP connector in Exchange  
2. Start the Microsoft Exchange Server 5.5 Administrator program, and then connect to the Exchange Server 5.5 computer.
3. In the Exchange Server 5.5 Administrator program, open the following location:
Organization\Site\Configuration container\Connections
4. Click Internet Mail Service, click Edit, and then click Delete.
5. In ADC manager, select the configuration Connection Agreement that you want, right-click the configuration Connection Agreement, and then click Replicate Now.
All outbound Internet mail now flows through the new bridgehead server. Locally-scoped address spaces are not permitted in Exchange 2000 Server environments. Only organization scopes and routing group scopes are permitted. For additional information, click the following article number to view the article in the Microsoft Knowledge Base:
257638 Locally scoped connectors not allowed in a mixed Exchange Server 5.5-Exchange 2000 environment

The above is an excerpt from the following KB article:
How to migrate from Exchange Server 5.5 to Exchange 2000 Server

Hope this helps. Let me know.

Author Comment

ID: 13512730
OK. Incoming was working so I did the 2nd portion; and rebooted both the 5.5 and 2k server. Now I get NDR's as follows:
         The e-mail address could not be found.  Perhaps the recipient moved to a different e-mail organization, or there was a mistake in the address.  Check the address and try again.The MTS-ID of the original message is:c=US;a= ;p=Paradigm Technol;l=MX1-050311000117Z-6
This is for an outside address, but it's acting as if it's supposed to be an inside recipient. The inside recipients still work as advertised.
LVL 27

Expert Comment

ID: 13513845
Are you saying that this NDR happens when a user outside your organization REPLIED to a message sent from an internal user when their mailbox was homed on the Exchange 5.5 server?
If the above is true, are the Exchange services on the 5.5 server turned off?

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Author Comment

ID: 13517067
No, NDR's were returned for internal users trying to send to outside mailboxes. I eventually solved the problem by about 1am. It turns out, what nobody was telling me all the info, that I NEEDED an SMTP connector on the Exchange 2000 Server: http://support.microsoft.com/kb/265293
Whereas previous articles on the KB had implied that the Default SMTP server was enough, well it's enough for the E2k server, not for the 5.5 server, which was lost without it's IMC. After configuring and reconfiguring the SMTP connector I eventually got it how it's supposed to be.
Other helpful articles for future people in this situation:
You would think mine would be a more common case; installing an Exchange 2000 server and making sure all mail flow works before taking the leap of moving all the mailboxes on to it.
Exchange Admin you'll probably get full points even though you only gave me half the story. Thanks for the half though, it got me on the right track.
LVL 27

Expert Comment

ID: 13518586
Hmmm.... create another SMTP connector. I would have thought that the default one would have worked also.
But if you look in the article that I posted it says:
Configure a new SMTP connector on the Exchange server that you want to be the bridgehead server for outgoing Internet mail. For additional information, click the following article number to view the article in the Microsoft Knowledge Base: ......

I guess maybe MS should have made this clearer.

Glad it is working now.


Author Comment

ID: 13536969
You're right, it was clearly in there. I must have skipped it the first time, but that was the article I came back to and used. MS did kind of treat it as an afterthought. The whole process is done except for dismantling the 5.5 servers. Thanks again for your help.

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