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Mail not being sent from my new Windows SBS 2008 server

Posted on 2009-07-14
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Last Modified: 2012-08-13
Hi all.  I have just installed Windows Small Business Server 2008 x64 on my Dell server, replacing SBS 2003.  I was very familiar with 2003 and am barely familiar with 2008.  I followed the wizards and did a little reading and have managed to set up my domain mail and a handful of users, however, I can't seem to get it to send mail.  The router has the right ports opened, as it worked well with 2003.  I am able to receive mail without an issue but for some reason, nothing I send from OWA gets to it's destination.  No error messages (that I know to look for) and the messages appear in my sent items.  I just don't know where they're going.  I did not set up a Smart Host as it appeared to be used as a relay server, which I don't believe I need.  My mail should come into and out from this box.  MX record is set to point to this box and it resolves correctly.  I'm sure someone more than vaguely familiar with SBS 2008 will be able to tell me exactly where to go and what to look at, as always.  Thanks in advance!
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Question by:BBMarc
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17 Comments
 
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Expert Comment

by:debuggerau
ID: 24855511
Did you run them up in parallel, Upgrade or migrate, or swing migrate the systems across?

Were you following instructions that we can follow your process?
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Author Comment

by:BBMarc
ID: 24856008
Did not run in parallel.  Took down the 2003 and put up the 2008.  No upgrade or migrate as this is not a business production server.  Just used by a few "friends" for a few websites, a few mail domains and FTP.  Did not follow any instructions other than the initial setup wizards.  When adding the mail domain, I tried to do what I knew how to do in 2003.  Found that things weren't quite the same.  :)
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Expert Comment

by:debuggerau
ID: 24856287
your items may be in the mail queue, awaiting to retry sending..

check the settings in the send connector,  it needs to have your FQDN defined.
http://technet.microsoft.com/en-us/library/aa998662.aspx

Or, if it is not configured at all:
http://www.petri.co.il/configuring-exchange-2007-send-external-email.htm
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Author Comment

by:BBMarc
ID: 24868535
I checked the existing send connector and it does have my FQDN in it.  I read the petri.co link and added an additional send connector, thinking there was something wrong with the first one the wizard had created.  Comparing the 2, the first and second were identical bu noticed the second, created manually, did not have the FQDN in it.  The petri.com procedure did not mention adding a FQDN and there was no option in the send connector wizard to do so.  For test purposes, I sent an email to an outside email box as well as an internal box.  The internal mail was received but the external mail was not.  Still no joy.
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Expert Comment

by:debuggerau
ID: 24874848
From the question can I take it that you are receiving emails externally, internally and can send internally...

So, if your able to receive externally, your port 25 is open, but to send, you'll be connecting to destinations on port 25, since the old box was working, I wonder if the send connector has been configured with SSL, is using a smarthost that doesnt exist, or the server your testing with is incompatible with the HELO EHLO format, or is set for secure STMP..

Do any of these things ring a bell when you set it up?


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Author Comment

by:BBMarc
ID: 24889254
Thanks for sticking with this debuggerau.  I'm not sure where the send connector would have beem configured for SSL but in reviewing the possible option available, I don't see SSL having been selected.  No SmartHosts are configured.  The testing server is GoDaddy and a number of others so I don't think the HELO option is an issue.  What I think is strange is that even though sent email shows up in my sent items, I never even see so much as a blink in the outbound queues.  Is there a way to turn on some logging to figure out what's happening to outbound messages?
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Expert Comment

by:debuggerau
ID: 24891750
you could set up logging, but not sure that is best yet..

How about looking at message tracking first, see if that gives a clue when you look at a message you had tried to send..

I'd also be looking at the routing groups too, in-case one was directing the traffic elsewhere..
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Author Comment

by:BBMarc
ID: 24910775
Can you tell me where to look at message tracking and routing groups please.  Not that familiar with SBS 2008.
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LVL 23

Expert Comment

by:debuggerau
ID: 24912023
sure, its in the Exchange Management Console..

For Message Tracking, look under toolbox (at the bottom)

For Routing Groups, look under Organization Configuration, then Hub Transport and look for 'send connectors'..
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Author Comment

by:BBMarc
ID: 24912993
I looked in Message Tracking for the lasat 3 months for "SEND" events and it found nothing.  No results.  I would have expected to see about 6-10 messages there.  

I then looked at Routing Groups but didn't really understand what I was looking at.  I saw the connectors I had created but none of the information looked incorrect or inappropriate.  For instance, the BBI External Connector I created manually said:
GUID: (number)
DN:CN=BBI External,CN=Exchange Routing Group (number),CN=Routing Groups,CN=Exchange Administrative Group (number),CN=Administrative Groups,CN=First Organization,CN+Microsoft Exchange,CN=Services,CN=Configuration,DC=byte-busters,DC=local
Proximity: Local Server
Total AD cost: 0
Scoped Connector: No
Address spaces: smtp:*,1
Connected domains: (none)
DNS routing enabled: Yes
Smart Hosts:


Should Connected Domains have something in it?  I'm not really sure.  The connector that was created automatically during the wizard configuration is identical with the exception of the GUID.
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Expert Comment

by:debuggerau
ID: 24920394
looks ok, well do you have the other server up? Is outlook referencing that one?

What out OWA, can you send, or even access that?
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Author Comment

by:BBMarc
ID: 24920531
What "other server" are you referring to?  Are you talking about the 2003 Server?  That one is down and all but gone in favor of loading this 2008 SBS.

On the current 2008 SBS, yes I can access OWA and I can remote into it.  During the testing of email send and receve, I used OWA exclusively.
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Expert Comment

by:debuggerau
ID: 24920627
ok, needed to check..

can't you even sent to yourself?
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Author Comment

by:BBMarc
ID: 24920698
Yes, I am able to send (and receive) to myself in OWA.
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Accepted Solution

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debuggerau earned 500 total points
ID: 24920809
ok, and you have a gmail account you can test to?

Now, I'm starting to wonder if DNS settings are correct?

You say you can receive emails ok, just not send..
So is it possible that the server is looking at itself only?
Have you a public DNS server to do lookups on?

so if you open a command prompt cmd.exe
and use the command
nslookup gmail.com

do you get all the IP addresses as a reply?
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Author Comment

by:BBMarc
ID: 24921158
Debuggerau, you won't believe this.  I get the stupid guy of the year award.  You probably would have figured this out earlier if you had all the details.  Mail from that domain is working properly.  I tested it with a yahoo account as well as 3 of my clients' accounts.  Mail was sent to and received from all accounts.  Here's the details; 2 domains were configure on the server, one that I was trying to get fully operational and one that was only partially configured, to be switched over when the first account was operational.  The second account (used for testing) is a fully operational account on a 3rd party server and was also partially configured on my server.  Apparently, when sending mail from the first domain to the second, it transfers internally and never actually leaves the server.  So my real working account from the third party never saw the emails sent from the first domain.  After getting successfuly mail transmissions to the other accounts, I decided to login to my server and check mail for the partially configured (test) domain.  Every piece of test mail I sent was in it's mailbox!  I want to apologize for wasting your time and appreciate all the help you gave me.  Had you not suggested I check mail with another account, I may not have discovered it for quite some time.  THANKS VERY MUCH FOR YOUR HELP!
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LVL 23

Expert Comment

by:debuggerau
ID: 24921262
no worries, ensure you close the question also please.
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