Sending Email Through SMTP on Exchange 2007 / SBS 2008

James Parsons
James Parsons used Ask the Experts™
on
I have SBS 2008 with POP3 connector setup. I'm receiving emails to the Outlook clients fine, however when I send an email from Outlook, it's not going anywhere. The recipient never receives it. How can I troubleshoot this??
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Barry GillChief of Staff

Commented:
you will havw to give us more info than that.
is the sender getting a bounce message or NDR (Non delivery report)?
Are the items still in the queue in Exchange?
Have you checked any of the logs?

Is your ISP a dial up?
If it is, chances are you are not allowed to send directly and you need to set up your default virtual smtp server to send to a smarthost and authenticate to that smarthost before it allows you to relay on its behalf.

Author

Commented:
Hi Barrulus

No bounce back message or NDR to the sender.

Looks like I can see them in the Smart Host queue viewer, however I can't seem to see any error logs as to why they're sitting there. ISP is not dialup.
Barry GillChief of Staff

Commented:
have you set your logging up to record smtp events?
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Author

Commented:
Okay, I've enabled logging as per: http://simultaneouspancakes.com/Lessons/2008/11/24/enabling-smtp-logging-in-sbs-2008/

I'll monitor them for a bit and see what comes through.

Author

Commented:
This was the message in the SMTP Send Log:

Windows SBS Internet Send *,,"Failed to connect. Error Code: 10060, Error Message: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond
Chief of Staff
Commented:
sorry about the delay...
Ok, that tells me there is either something wrong with your SMTP smarthost config OR there is something wrong with the receiving server.
I would hazard a guess as well that if you have a firewall it *may* be causing the issue.
First thing to check is can you telnet from cmd on the machine to the smarthost on port 25
if you can then your problem is not the firewall.

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