Exchange 2003 -> 2010 coexistence (One way mail)

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Jacob-Dixon

Ok I just can't figure this out and have a dent in my desk now.

I have implemented Exchange 2010 in our organization. We are moving from Exchange 2003. So we are running two servers (Exchange 2003, win server 03 sp2) and Exchange 2010 (win server 2008 r2).

I can SEND mail FROM Exchange 2003 to the outside, other 2003 users, and to 2010 users.

I can SEND mail FROM Exchange 2010 to he outside, other 2010 users, but not 2003 users.

I can receive from outside users to both 2003 and 2010.

So why can't Exchange 2003 users get email from 2010?

Exchange 2010

-> Send Connector (generated auto), SMTP, Address *, Cost 10, Network route through relay.dnsexit.com as smart host, Smart host auth, authenticationMechanismLabel

Receive connectors have anonymouse users set and were auto generated on install

Exchange 2003

I have one SMTP Virtual Server, and two routing groups.
 
J

Jacob-Dixon

Sorry about my last post. Never got finished.

Ok I got it working now but it doesn't seem like it should be working. Here is what I have:

Exchange 2003

SMTP Virtual Connectors

Default SMTP Virtual Connector (Disabled )
NewSmtp (Enabled )

Routing Group Connectors (one routing group)

[2003 to 2010] Connector:
Connects this routing group with: Exchange Routing Group (DWBGZMFD01QNBJR) Any local server can send amil over this connector Remote Bridgehead is EX2010 using the Default SMTP Virtual Server (which is disabled)

[External SMTP] Connector:
Forward all mail through this connector to the following smart hosts: relay.dnsexit.com Local bridgeheads: EX2003 using NewSmtp Virtual Server No Connected Routing Groups Address Space is SMTP, *, 1 Entire Organization

[Interop EX] Connector:
This was created with exchange and technically shouldn't be being used because it has the Virtual Server set to Default SMTP Virtual Server which is Disabled . So if I'm correct I could just delete this (this is the 2010 created one)

Exchange 2010

[Organization Configuration - Hub Transport]

[External SMTP] Send Connector:
Address Space: SMTP, *, 1 Network Route mail through the following smart hosts: relay.dnsexit.com Smart host authentication: authenticationMechanismLabel Source Server: Nothing.. Blank

[External] Send Connector:
Address SpacE: SMTP, *, 1 Route mail through the following smart hosts: relay.dnsexit.com Smart host authentication: None Source Server: EX2010

Ok so this completely works. I can email out from both servers, I can exchange emails between the servers, etc. The problem is I just don't think its correct .So if I'm correct, what I think we should have is one routing gruop connector with a local of EX2003 and a remote of EX2010 using a enabled SMTP Virtual Server. This will route mail to EX2010 right? So then EX2010 will perform the sending over the email?

The problem is when I tried this, everything seemed to work EXCEPT EXchange 2003 sending to the outside world. Does anyone have a diagram or detailed information of this? I have googled quite a bit and just not finding exactly what I am looking for.
 
J

Jacob-Dixon

Nevermind I still can't email from exchange 2010 to 2003.
 
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Mike Crowley [MVP]

When you run get-routinggroupconnector from your 2010 box, do you get two lines or one? RGCs are one-way.
Additionally, what queue does mail sit in when it doesn't send out?

Mike Crowley
Check out My Blog!
 
J

Jacob-Dixon

Ok I deleted the Internet Send connector I created on the Exchange 2010 box. So the only send connector I have now is the one that Exchange created when installing.. which is related to the smtp connector on Exchange 2003 I assume.

I get three RoutingGroupConnectors.
Interop Ex - Exchange Routing Group - first routing group Interop Ex - first ruoting group - Exchange routing group 2003 to 2010 - first routing group - Exchange Routing Group

Ok so you are probably wondreing why I have three. The 2003 to 2010 was created using the Exchagne 2003 console. The problem is the Default SMTP Virtual Servre is disabled and when creating a routing group with Exchange 2010 it ALWAYS chooses that one. You can't change it unless you use ADSI edit. (from what I can figure out)

So as I sit right now I can email everyone except from 2010 to 2003. I am still at the setup above minus the:

[External] Send Connector:
Address SpacE: SMTP, *, 1 Route mail through the following smart hosts: relay.dnsexit.com Smart host authentication: None Source Server: EX2010

Do you have an example how I should be?

From what I gather on how it is suppose to be I should only have one routing group connector on exchange 2003 that goes from EX2003 to EX2010 (remote bridgehead). That way all email going out from 2003 gets moved to 2010 and then 2010 sends out correct?
 
M

Mike Crowley [MVP]

I get three RoutingGroupConnectors.
Interop Ex - Exchange Routing Group - first routing group Interop Ex - first ruoting group - Exchange routing group 2003 to 2010 - first routing group - Exchange Routing Group

Ok so you are probably wondreing why I have three. The 2003 to 2010 was created using the Exchagne 2003 console. The problem is the Default SMTP Virtual Servre is disabled and when creating a routing group with Exchange 2010 it ALWAYS chooses that one. You can't change it unless you use ADSI edit. (from what I can figure out)

I believe this is your problem. Please re-enable that virtual server - Exchange 2010 is trying to connect to it. Remember, connectors are one-way, so yo need two working connectors for proper mail-flow.

This has nothing to do with the send connector BTW. you can put that back if you want.

Mike Crowley
Check out My Blog!
 
S

Syed MM

Hey Does the messages land up in the queue of Exchange 2010 or users get an NDR If it lands up in the queue - whats the last error that u get ?Syed MM MSFT
 
J

Jacob-Dixon

As it sits right now the Exchange2010 server shows a:

" 421 4.4.2 Connection dropped due to SocketError"

I think with that Extra Send Connector I almost immediately got a NDR back instead. I'm giong to have to add it back to test because I just can't remember. I've been changing this up so much I've forgotten where I was at that point.
 
J

Jacob-Dixon

But when I fixed the Connector where it could talk and I saw the messages when I sent from 2003 to 2010 I could see in the message viewer where it " transferred to 2010" . But the problem was if I was sending to an external email it would not send.

Example:

Message tranferred to EX2010.domain.local through SMTP

I got that when tyring to send to like a gmail accuont buti never got to gmail accuont. I couldn't even see it in queue viewer in 2010
 
M

Mike Crowley [MVP]

But when I fixed the Connector where it could talk and I saw the messages when I sent from 2003 to 2010 I could see in the message viewer where it " transferred to 2010" . But the problem was if I was sending to an external email it would not send.

Example:

Message tranferred to EX2010.domain.local through SMTP

I got that when tyring to send to like a gmail accuont buti never got to gmail accuont. I couldn't even see it in queue viewer in 2010
This is the first time you mentioned an issue with sending to the internet. Let's table that for now and only focus on the 2010 --> 2003 problem.

Please enable the virtual server as I said above and post back. Also delete that 3rd RGC.

Mike Crowley
Check out My Blog!
 
J

Jacob-Dixon

Ok.. give me a little bit to do this because I think it might cause a email issue. I didn't bring this up at first because the way that the configuration sites " right now" does not do that error. That error only occurred last night when I was trying to change everything and to get it working.

I will enable that and get back to you. Thank you both for the help already! It should only be couple hours before I do those changes
 
J

Jacob-Dixon

Ok I did what you asked and now thats where I get to where I can exchange emials between 2003 and 2010.. but 2003 can NOT send to outside (like gmail). I can receive in though.

I get:
Jacob Dixon on 10/8/2010 6:41 PM
A configuration error in the e-mail system caused the message to bounce between two servers or to be forwarded between two recipients. Contact your administrator.
<server.domain.local #5.3.5>
 
J

Jacob-Dixon

Well I got it working!

So on my routing group connecters that I have for 03 I have it using the default virutal connector. That is all I have.. not even a SMTP connector.

Now on Exchange 2010 I have a intenret send connector that I created with exchagne.

So all email is being routed through EX2010. I have testd it multiple ways and it seems to be working. I deleted the 2nd virtual server. The weird thing is even after I deleted it I noticed that it was still trying to use it?? I could see it in the queue when trying to send some emails to like 2010 as the source being the 2nd virtual server.

So when I ran into that problem I knew for some reason exchange was holding on to it even AFTER I deleted the dang virtual server! So... I just restarted all the services and it started routing EVERYTHING through the default. Now everything is working great.

Thanks so much for your guys help
 
J

Jacob-Dixon

Well it looks like i'm not 100% yet. This is weird...

I seem to be able to email sometimes using OWA but not Outlook? When I look in the queue viewer I do not see any problems (errors) except some in queue:

Last Error: 400 4.4.7 The server responded with: 554 5.1.0 Sender Denied. The failure was replaced by a retry response because the message was marked for retry if rejected.
Queue ID: ********-EX2010\220
Recipients: journal@*********.com journal@*******.com

It seems something with the journaling is screwing it up. Any ideas?
 
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