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SBS 2008 exchange SMTP connector issue

Posted on 2010-08-30
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Last Modified: 2012-06-27
I have an SBS 2008 server set up to retrieve POP3 email from an outside domain. The POP3 works fine on receive and the workstations Outlook is working perfectly to retrieve the email.

I don't think I have the SMTP connector set up right. They get emails back with this below when they send from their workstations.

#550 4.4.7 QUEUE.Expired; message expired in unreachable destination queue. Reason: A matching connector cannot be found to route the external recipient ##

Thank you in advance for your help!

I should mention that I do not believe I need a smart host.  When I configure the POP3 email right on the workstation only I do not need anything to do with the ISP.
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Question by:dgrenda
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Expert Comment

by:mattibutt
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is your pop service running is your firewall allowing port 110
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Author Comment

by:dgrenda
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they need 995 and the pop service is running. They can receive email fine through exchange.
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by:Jamie_Wilson
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If your exchange server is pop collecting, how are you linking the workstations to exchange? via the exchange button in outlook or via pop3?
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by:mattibutt
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have enabled exchange anywhere
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by:dgrenda
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Jamie - I set up the email account in outlook using the exchange server option and it set up successfully.  I do not have POP3 set up on the workstations.

matt - Why is that important?  I am asking.
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by:markusdamenous
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The POP3 connector is being used to download mail into Exchange from an externally hosted POP3 account.  Exchange 2007 does not know by default how to route outgoing email.  You need to create a SEND connector - this could either be a SMARTHOST to your ISP SMTP servers, direct to the internet via DNS.
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by:Jamie_Wilson
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Disable it for now, and connect directly to exchange internaly, see if you get the same problem

also, can nslookup the domain you are trying to send mail to on the exchange server?
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by:mattibutt
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just ruling out all the possiblities the last one is not that relevant
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by:markusdamenous
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by:Jamie_Wilson
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@markusdamenous

SBS has a default send connector
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by:dgrenda
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Mark - Yes I think I just need to set up the SMTP side....I don't need the smart host thing I don't think.  Where do you do this?

Jamie - can you explain nslookup?  Sorry.
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by:Jamie_Wilson
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by nslookup, i meant to make sure your exchange server can find the mx record of the domain you are trying to send to as the default SBS send connector uses DNS to find the domain

and to test it, here is a link:

http://surf11.com/entry/84/how-to-do-mx-lookup-windows

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Author Comment

by:dgrenda
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Ok, in the Hub Transport section I see the default Internet Send connector and I have the "*" in the address.

Do I need to set up a seperate specific SMTP connector for the SMTP computer I want to route outbound email through?
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by:Jamie_Wilson
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You shouldn't need a separate SMTP connector.

Will nslookup work for MX?  
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by:dgrenda
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Jamie it does see the MX record of the domain.
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by:dgrenda
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Ok, so the default SMTP connector should be the only one I need? The seperate one I set up is not necessary?

And "*" is in the address space?

How does Exchange know which SMTP server I want my email routed through then?

Maybe tell me how to set up the default send connector.
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by:Jamie_Wilson
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no, there is no need for a 2nd one.

the default one should look like:

Address Space:

Type:
SMTP

Address:
*

Cost:
1

Network:
Use DNS "MX" Records to rout mail automatically with Enable Domain Security not ticked

Sorce server;

Should be its self

as for your question on which smtp will be used, that is what the address space is for, but as it is * everything will go through it
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by:dgrenda
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Ok I understand. But the SMTP server their email should be going through belongs to an outside domain. So the SMTP server name is  smail.xxx.com

So if the user sends an email to joe@abc.com  how does Exchange know to route that outbound email through the specific SMTP server smail.xxx.com?

Isn't there someplace I should be specifying smail.xxx.com?


Sorry for all this. I REALLY appreciate the help.
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by:markusdamenous
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The * in the SMTP connector your end, is the only connector in place.  Therefore, the xxx.com domain fits into the scope of that connector.  That connector is configured to use DNS to route email, so it does the MX lookup and sends it there.

I didnt realise that Exchange 2007 under SBS 2008 auto creates a send connector, apologies.
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by:Jamie_Wilson
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did you go through the setup your internet address section of the sbs wizard?
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by:dgrenda
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Jamie - no I did not.

Why is that important?  
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by:Jamie_Wilson
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That configures half of exchange for you.

I recommend you run through that and see if you have the same issues
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by:dgrenda
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They use a completely outside domain for their email that is hosted someplace else.

I do not have control of the domain. I only know the email account settings and domain mailbox usernames and paswords.

DO I still run the wizard?  And do I pick "manage myself"  or  "let server manage"
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by:Jamie_Wilson
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You will need to run the wizard to add the domain into exchange, this is for the 'reply to' email address if nothing else

pick manage myself (this will assume that the mx record will point to the server but will be receiving mail via a pop collect so doesn't really matter)
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by:dgrenda
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I rant the wizard and got all good except a warning about SBS not being able to open ports 80, 25, 443, 987. I opened them on the linksys router and re-ran the wizard but still get the warning.

suggestions?


thanks for hanging in with me.
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by:Jamie_Wilson
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Dont worry about that (its allways said that for me)

do you get the same problems when sending mail now?
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by:dgrenda
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Yes. I can send the email from the workstation and it appears to go. It just never shows up at the destination.

I am not getting kick back messages any more. It just doesn't show up. I am emailing my own email account at my own domain from the workstation on the network. I am logged in remotely.
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by:dgrenda
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This whole thing sucks green donkey nuts.
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by:Jamie_Wilson
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Try rebooting the server now you have made the change (stop the information store 1st)

I whould RDP on to the server instead of using outlook anywhere as that could be causing the problem?
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Author Comment

by:dgrenda
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I am using LogMeIn. So it's not outlook anywhere.

I appreciate all your help man.  What time do you have to quit helping me for the day?  I am in Phoenix, AZ  it is 2PM here.

I will restart the server.
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by:Jamie_Wilson
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log me in onto the server its self?
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by:Jamie_Wilson
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And i have around 20 min
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by:dgrenda
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The product LogMeIn  is how I support the machines. I am at my office and can have all the machines in front of me at once.

THank you very much. I will keep working on this and update you with what I find.

I wish I could hand out more than the 500 points.
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by:Jamie_Wilson
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How did it go?
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Author Comment

by:dgrenda
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Well, I could not get that connector to work. I left it a single connector, configured as you said ( "*", etc) . I ran the internet address wizard successfully except for the router errors.  When I send an email from the workstation it just leaves the Outlook outbox and never goes anywhere.

Curiously, when I change the connector to use an INVALID smarthost, I get relay reject kick back emails for ALL the emails I had previously sent but didn't go anywhere. It's like they were sitting in the outbound queue the whole time not getting sent...and then they all try an go with the invalid test smart host.

I ended up configuring each workstation to get it's own POP3 email while still using Exchange for the calendar, etc. It all looks the same to the user.

Any more ideas?
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Jamie_Wilson earned 500 total points
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You should be able to set your ISP's smtp server as the smart host, try that
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Author Comment

by:dgrenda
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Yeah that was my next idea. I tried just using their SMTP server as the smart host but it was rejected. Around here the ISP are super uptight about spam so I need to track down the username and password for the settings.

I'm going to give you the points anyway because I appreciate the value of your advice and I did learn a lot.

If you don't mind my asking, I'm always interested in knowing what part of the world the folks who help me are from?  Are you in the US?

And one more thing I'm not sure I understand:

So you are saying that the connector is supposed to use the xxx.com DNS resolution of the SMTP server to know where the outbound email server is?  I did the telnet mx 25 thing for the DNS name of the mail server and it DID reply back that it found it.  So strange that the mail just isn't going.

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Author Closing Comment

by:dgrenda
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Thank you for your patience and assistance on multiple angles with this issue. Excellent work.
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