Question

TLS and SMTP Bridgehead Server not working right

Asked by: jhyiesla

I have an Exchange 2003 environment.  I have several routing group connectors set up to handle various connections. One is designed just for sending email to the Internet. The others are for connections to partner email servers.  All use the same SMTP Virtual Server.

I want to implement TLS to our email filtering service. I have had TLS working on outgoing emails for almost a year since the outgoing is controlled by the connector and TLS is set on the connector.  Our partners do not support TLS.  Now I wish to implement TLS incoming from the email filtering service.

Here's what I have done.  I have created a second SMTP Virtual Server and I have checked in the Authentication area for it to use TLS. I have applied our SSL cert to the VS as well. I then went to the routing group connector for the Internet email connection and I removed the Default SMTP VS and added in the new one. I then bounced both SMTP VS's.  Initially I still saw outgoing email being processed through the old VS. I reinstalled the old VS into the connector, waited for the email to clear and then removed it once again, bouncing the SMTP VS's between each change. Finally I saw outgoing emails being processed through the new SMTP VS.

Then we started our testing by enabling TLS on the email filtering service.  This failed. We could see TLS activity in Wireshark, but for whatever reason, it wasn't being processed into the mailbox. So we played around with it  and never figured that out. Anyway, we set the email filtering service back to a setting where TLS was preferred, but could send it by SMTP.  Then we started getting in emails via just plain old SMTP.  .  

Now, if I have the connector pointed to the SMTP VS that is set only to do TLS, how are we getting in regular SMTP emails?  

Subsequently we decided to just leave it for now and work on it later.  We found then that we could no longer process outgoing emails.  I checked the queues in the Exchange server and could see that outgoing emails were queued on the old SMTP VS, which is NOT any longer specified in the connector as the one to use.  I added back in the old VS so that both are in the connector and now emails are going both directions again.  Incoming TLS still doesn't work, but whatever...

So a second question is how are outgoing emails falling into the old VS when only the new one was specified in the connector?  Is there some other service that I should have bounced?  At one point we did bounce the SMTP Service.  I really don't want to reboot the entire server.  Any thoughts are appreciated.

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Asked On
2009-09-10 at 10:25:16ID24722191
Topics

Exchange Email Server

,

Email Protocols

,

Simple Mail Transfer Protocol (SMTP)

Participating Experts
1
Points
500
Comments
5

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Answers

 

by: MesthaPosted on 2009-09-10 at 14:09:19ID: 25304384

Why did you touch the routing group connector?
That has nothing to do with email from the internet and should not have been touched.

Furthermore, all the selection of the SMTP virtual server in the Connectors do is point the traffic at a certain server. You cannot actually control which SMTP virtual server is used.

Therefore what I would have done is left everything alone.
Setup a second SMTP virtual server for incoming email only. Use the SMTP connector for outbound email.

Simon.

 

by: jhyieslaPosted on 2009-09-10 at 19:50:13ID: 25306397

Well, as I said above, I have several connectors that I have set up over the years to do different things.  Each of them shows as a "bridgehead" server the Default SMTP Virtual Server.  I realize that the connector has to do with outgoing email.  And I set that ages ago to use TLS and that works OK.  I assumed that since I needed to set up a second SMTP VS to handle incoming Internet email with TLS, that I had to drop that one in the Internet Email connector. And basically it worked from a connection standpoint for a while, but then the outgoing traffic switched back to the Default SMTP VS that was no longer listed in the connector.

I'll take a closer look at this tomorrow when I'm back at work.  But what's the reason to specify the SMTP VS in the connector if it's going to pick what it wants anyway?

 

by: MesthaPosted on 2009-09-11 at 01:53:59ID: 25307636

There is no reason to choose a specific connector. It was explained to me once, but it is something like Exchange asks IIS for an SMTP connection and IIS gives it one, It could be from any of the SMTP virtual servers. Its painful and annoying and that is why I tend to only use additional SMTP VS for inbound email.

Simon.

 

by: jhyieslaPosted on 2009-09-11 at 06:13:21ID: 25309009

OK...

I'll have to go back to my web filtering service to attempt to solve the TLS issue.

Can you answer this?  Before yesterday, I had both SMTP VS's set up, but only the default one was listed in any of my three connectors.  As far as I know I had no issues sending or receiving emails.  After I removed the Default VS from the Internet connector and added in the new one it worked for awhile, but then outgoing mail stopped.  I assume that it's because the email was queued to the default VS, but that VS was not listed in the connector. I make that assumption because as soon as I added it back in to the connector email cleared from that queue and has been working ever since.

So if your assertion is correct that outgoing mail can use either of these connectors at will, why, for the last year, has the system "apparently" never used anything other than the Default VS, because as far as I know we have never received any NDR messages like I got yesterday?

Thanx...

 

by: MesthaPosted on 2009-09-11 at 10:24:42ID: 25311617

Unless the two connectors were identical, a change in configuration may well have caused the problem.
Furthermore, changes to the routing configuration are not instant. Exchange has to pick them up which can take a little while unless services are restarted. Therefore a change can appear to work for a little while, because in reality, the previous configuration is still being used.

The behaviour with SMTP and the connectors has always been a bit hit and miss, probably because it rides on top of IIS. The problem goes away with Exchange 2007 as the Exchange team have gone to their own transport stack.

Simon.

20120131-EE-VQP-002

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