Depends on where you have smarthost configured. If it's on a smtp connector, that would be the proper behavior (but even that can be overridden if you've specified a masquerade host).
If it's on the default smtp virtual server, that overrides everything. Regards, Michael B. Smith Consultant and Exchange MVP http://TheEssentialExchange.com From: Paul Steele [mailto:paul.ste...@acadiau.ca] Sent: Thursday, April 22, 2010 2:51 PM To: MS-Exchange Admin Issues Subject: RE: Two questions - Exchange 2003 & 2010 That revealed that puzzle. Mail destined to Exch2010 was being routed up to our Unix smart host. I thought that Exchange would first check to see if the recipient email address was present in Active Directory and route to the appropriate Exchange server before sending the mail to the smart host. I obviously have more reading to do. It's difficult when our single Exchange 2003 server was installed 7 years ago and you sort of forget how everything all works! From: Michael B. Smith [mailto:mich...@smithcons.com] Sent: April-22-10 2:32 PM To: MS-Exchange Admin Issues Subject: RE: Two questions - Exchange 2003 & 2010 You can enable protocol logging on the Exchange 2003 server and receive-connector logging on the Exchange 2010 server (connection logging is on by default). You can see from those logs why communication is failing. Regards, Michael B. Smith Consultant and Exchange MVP http://TheEssentialExchange.com From: Paul Steele [mailto:paul.ste...@acadiau.ca] Sent: Thursday, April 22, 2010 1:30 PM To: MS-Exchange Admin Issues Subject: RE: Two questions - Exchange 2003 & 2010 Unfortunately there seems to be some other issue. We simply can't get mail flowing from EXCH2003 to EXCH2010. It's obviously some sort of communication issue since the Public Folders aren't replicating either. The various settings in the default receive connector look correct. I've verified that port 25 on EXCH2010 is open to EXCH2003, but still no go. I've read some good documents on the various post-installations steps that should be performed and we've completed all of them. We may redo our test installation and see if we have better results. I guess this is why we set up test environments before tackling the real thing... From: Michael B. Smith [mailto:mich...@smithcons.com] Sent: April-21-10 10:14 PM To: MS-Exchange Admin Issues Subject: RE: Two questions - Exchange 2003 & 2010 Well, you've identified the problem. You shouldn't have disabled the default receive connector. If you take a look at it, you'll see on the "Permission Groups" tab, that "Legacy Exchange Servers" is one of the options. Exchange servers speak to each other using a number of extensions to the SMTP protocol. Those extensions are only allowed when you enable the permissions. The default receive connector allows those permissions from Exchange servers (2007/2010) and legacy Exchange servers (2003). However, the Internet receive connector should only enable "anonymous". Generally speaking, most people just enable the "anonymous" permissions on the default receive connector so they can get by with a single connector. And to answer your other question - Outlook and Exchange preferentially communicate using MAPI, not SMTP. Regards, Michael B. Smith Consultant and Exchange MVP http://TheEssentialExchange.com From: Paul Steele [mailto:paul.ste...@acadiau.ca] Sent: Wednesday, April 21, 2010 8:45 PM To: MS-Exchange Admin Issues Subject: RE: Two questions - Exchange 2003 & 2010 I spoke too soon. The change allowed a manual telnet session to work, but mail initiated from Outlook still gets hung up. Does Exchange use standard SMTP/port 25 protocol for inter-Exchange email transfers, or does it use something different? From: Paul Steele [mailto:paul.ste...@acadiau.ca] Sent: April-21-10 9:06 PM To: MS-Exchange Admin Issues Subject: RE: Two questions - Exchange 2003 & 2010 We did run the command but everything looked ok, at least to us. The Get-receiveconnector has so much information it's not entirely easy to decipher, this being our first Exchange 2010 server. I think I have narrowed down the problem though. When I tried a manual mail session using "telnet exch2010 25" from exch2003, when I give the "mail from:usern...@acadiau.ca", I get the error "530 5.7.1 Client was not authenticated". That gave me the clue I needed to at least find a workaround. During the 2010 install, a Receive connector was created in the Server Configuration Hub Transport section for handling mail coming from EXCH2003. I disabled that connector so that mail coming from exch2003 would arrive using the SMTP connector I had created for mail coming from the Internet. Since that one had no authentication requirments that solved the connectivity problem for mail coming from exch2003. That brings up another question. Should there be a separate Receive Connector for Exch2003 to Exch2010 mail (one which enforces authentication) and another one for normal (Internet) mail? From: Michael B. Smith [mailto:mich...@smithcons.com] Sent: April-21-10 8:29 PM To: MS-Exchange Admin Issues Subject: RE: Two questions - Exchange 2003 & 2010 That's why I suggested you execute this command, and examine all the information output from it: get-routinggroupconnector | fl This is a PowerShell command, you'll execute it from the Exchange Management Shell on the 2010 server. You might want to do the same thing with "get-receiveconnector | fl" and "get-sendconnector | fl". While there are another potential knobs and switches involved, with the output from those 3 commands we will likely be able to identify any culprit or provide an additional lead to continue the investigation. Regards, Michael B. Smith Consultant and Exchange MVP http://TheEssentialExchange.com From: Paul Steele [mailto:paul.ste...@acadiau.ca] Sent: Wednesday, April 21, 2010 7:00 PM To: MS-Exchange Admin Issues Subject: RE: Two questions - Exchange 2003 & 2010 I thought I would add a bit more info to Tammy's first question. Our two test servers are called EXCH2003 and EXCH2010. After the 2010 installation, two connectors were created and appear when using Exchange System Manager. In the First Routing Group (associated with EXCH2003), the new routing connector was called EXCH2003-EXCH2010. In the Exchange Routing Group (created by the 2010 install), another connector was created called EXCH2010-EXCH2003. These connectors cannot be modified with Exchange System Manager (complains that version 8 is required). Our understanding is that the first connector controls mail going from EXCH2003 to EXCH2010, while the second one controls mail from EXCH2010 to EXCH2003. They appear to configured properly, but obviously something isn't quite right. Email works from mailboxes on EXCH2003 to mailboxes on EXCH2003, from EXCH2010 to EXCH2010, and EXCH2010 to EXCH2003. However, EXCH2003 to EXCH2010 does not work, so our guess is that the EXCH2003-EXCH2010 connector is the one that is not working properly. If anyone has any suggestions on what to look for we would really appreciate it. We don't want to proceed with the production upgrade until we get all the details working in our test environment. Thanks! From: Michael B. Smith [mailto:mich...@smithcons.com] Sent: April-21-10 2:56 PM To: MS-Exchange Admin Issues Subject: RE: Two questions - Exchange 2003 & 2010 The cover article in May's WindowsITPro covers Exchange 2003 to Exchange 2010 migrations and covers everything that you have to set up for it to work properly. It'll be out next week. (I should know, I wrote it.) As a guess, without further information, I would guess that you do not have a bi-directional routing group connector or if you have one, it isn't properly configured (get-routinggroupconnector | fl <-- from the Exchange Management Shell). Insofar as your second issue - if you want to change the retry interval, that's fine. But I would consider this more of a postfix issue. IMO, instead of returning a 450 error, postfix should be returning a 5xx error. Regards, Michael B. Smith Consultant and Exchange MVP http://TheEssentialExchange.com From: Tammy George [mailto:tammy.geo...@acadiau.ca] Sent: Wednesday, April 21, 2010 1:36 PM To: MS-Exchange Admin Issues Subject: Two questions - Exchange 2003 & 2010 We are preparing to upgrade to Exchange 2010 from Exchange 2003. We presently have a test environment setup. Our 2003 test server is unable to send to our 2010 server. We can send from 2010 to 2003 and from 2010 to Internet addresses (i.e. non acadiau.ca addresses) but we're unable to send from Exchange 2003 to Exchange 2010 and from Exchange 2010 to other non-Exchange addresses within our domain (i.e. acadiau.ca addresses on other servers). Exchange 2010 appears to be trying to deliver them locally. Any pointers? Everything appears to be configured properly but obviously we've missed something. Also - our Exchange 2003 server occasionally gets tied up trying to deliver messages to domains that are registered but their DNS servers aren't answering to accept email (1800thriller.com just this afternoon for example). Our Exchange 2003 server is configured to send through a Postfix server before going on to the Internet. Our Postfix server is sending the message back to Exchange with a 450 error. Exchange retries 1 minute later. And as is configured, this continues for 2 days until Exchange gives up (or if we delete before then). This isn't usually a problem unless 3 or 4 outgoing emails get in this state at the same time then all outgoing email comes to a halt. I previously read about this issue and the fix I found mentions to not make the change unless Microsoft Support Services advises (the only URL I can find this aft is http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_24771370.html. it references Exchange 2007 but it's the same sort of thing for 2003) We've been addressing this issue as it arises and we're hoping it'll disappear once we migrate to 2010. I was hoping someone on this list might know the answer to that for sure. Huge thanks in advance & my apologies if these questions have already been asked & answered. -- Tammy George Sr. Systems Operator Technology Services Acadia University tel: (902) 585-1158 fax: (902) 585-1066
