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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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Last Modified: 2012-05-10
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
ID: 34137507
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_
ID: 34138452
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
ID: 34138867
> 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
ID: 34142986
you'll have to look at the logs to view the reason for the problem....
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by:ob1_
ID: 34145258
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
ID: 34145761
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_
ID: 34147242
Strange - still nothing. Do I need to check anything on the advanced tab in SMTP logging?
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by:Rich Weissler
Rich Weissler earned 500 total points
ID: 34148238
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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by:ob1_
ID: 34168468
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
ID: 34170187
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_
ID: 34170219
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
ID: 34173790
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_
ID: 34176978
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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