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Mail stuck in SMTP queue (C:\inetpub\mailroot\Queue) on Windows Server 2008

Posted on 2010-11-15
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I have a Windows Server 2008 box with IIS7. I have added the SMTP role/feature in Server Manager.  I have an asp web page that sends mail from the server to 1 or 2 support addresses over the internet.

This worked fine on our 2003 box. We have upgraded to 2008 and now mail is stuck in the queue folder.

If I go into IIS 6.0 Manger I see that the SMTP Virtual Server is started. Any ideas?


thanks,
Bobby
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Question by:ob1_
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Rich Weissler earned 500 total points
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Have you turned on logging on the SMTP server, and looked in the logs to see if the messages are attempting to send and failing for some reason?

Are the 1 or 2 support addresses configured to accept traffic from the new Windows 2008 server?

(In my environment, for example, outbound traffic on tcp/25 is refused by router ACLs.  SMTP servers have to send mail through a smart host configured inside the network, which then only relays traffic from approved hosts.  This prevents random machines from becoming infected with malware which turns the workstations into SPAM generators.)
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by:ob1_
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Ok I have turned on logging.

I am not sure if the support addresses are configured to receive mail from the Windows 2008 Server - I don't have any admin access to that system.

Does a smart host get configured with MX records on the internet like a regular mail server? Maybe the old server had a smart host on it I am not sure...


thanks,
bobby
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by:Rich Weissler
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> I am not sure if the support addresses are configured to receive mail from the Windows 2008 Server - I don't have any admin access to that system.
*nod*  Logging should show you pretty quick.

Smarthost is a setting within SMTP -- it defines where to send mail.  (It also simplifies troubleshooting outbound mail issues.)  If it was set on the old server, it'll probably be a good idea to set it to the same on the new server.  Screen shot on where the setting lives attached. Where to find smarthost setting in the IIS 6 Manager.
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by:sufianmehmood
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you'll have to look at the logs to view the reason for the problem....
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by:ob1_
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I turned on logging yesterday and sent an email from the website but strangely enough there is no SMTP folder or log file in C:\Windows\System32\LogFiles... any ideas on that?



thanks,
Bobby
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by:Rich Weissler
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Yeah... that's the default location (in c:\windows\system32\LogFiles\SMTPSVC1\<blah>.log)
But... I've had enough wacky/crazy/stupid stuff happen with UAC in Windows 2008 that I'm going to suggest this -- go ahead and tell it to log to a different location.  Create a new directory, and make certain the system has permission to write to the directory.

And/Or .. .make certain to stop and restart the SMTP service after making changes.
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by:ob1_
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Strange - still nothing. Do I need to check anything on the advanced tab in SMTP logging?
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by:Rich Weissler
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No... you shouldn't have to do anything.  BUT -- on researching, there are some versions of 2008 for which there is a bug in SMTP logging.  See if this blog matches your situation:

http://weblogs.asp.net/steveschofield/archive/2008/02/29/windows-server-2008-smtp-service-logging-tip.aspx

(It looks like you might need to "Install ODBC Logging module (role service in Server Manager)" -- then stop and restart SMTP service.)
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ok.. i have a 64 bit OS so this makes sense.

i have added the role service, moved the logging folder to the D: partition, granted full permissions to the System account and Administrators group, restarted SMTP service and IIS, stop/started the virtual server, and telnetted from a command prompt to localhost and google.com.

both return "could not open connection to the host on port 23: connection failed" - should this be enough to create a log entry? i set the log schedule to hourly. still the log folder is empty.


thanks for your help!
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by:Rich Weissler
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Are you trying to get mail into this server, or out of?  
If you want to test receiving mail -- telnet to tcp/25 on this server... but I suspect that isn't want you want.

Try sending another SMTP message out... that should generate some log traffic.
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by:ob1_
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i am trying to send mail from the server not receive it. i sent a new message and still no log :(
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by:Rich Weissler
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Okay, dropping back -- what queue folder is the mail stuck in?  (This is starting to sound like the computer twilight zone...)
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by:ob1_
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no doubt - turns out the ISP was blocking traffic I believe on port 25. we contacted them and everything is working great now. thanks for all your help!
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