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emails stuck in IIS SMTP queue - relay to Exchange 2010

Posted on 2014-04-03
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Last Modified: 2014-04-03
I have a Windows 2003 64bit server that is a SMTP relay server.  It filters emails with GFI MailEsesentials and then relays them to Exchange 2010.  It only uses IIS SMTP.  Emails are stuck in it's queue.  I look in my Exchange 2010 event logs and I don't see anything pertaining to back pressure.  I see no errors or even warnings.  So, I assume it's something to do with my SMTP relay server.  Any ideas?
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Question by:gopher_49
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Expert Comment

by:SieQ
ID: 39975097
Check the logs on Windows 2003 64-bit + enable logging on SMTP server on IIS
http://www.iislogs.com/steveschofield/want-help-with-iis-smtp-service-please-enable-logging
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by:Enphyniti
ID: 39975098
Are you logging SMTP on the 2003 system?  If not, turn it on and take a look at the logs.

Have you tried restarting smtp on the 2003 system?  How's disk space?
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Author Comment

by:gopher_49
ID: 39975116
I rebooted the server for it's only a SMTP relay and that will restart the SMTP service and all GFI services.  The queue is now processing.. But..  I'm curious to if it was a GFI software issue or IIS/SMTP.  I have logging enabled.  I opened the log in a SMTP viewer called ES-Insight.  I see a ton of 'out of sequence SMTP commands'.  But those are all SPAM.  I don't see anything legit with that error.. What should I be looking for?  I see the below commands on emails being held up that are NOT spam..  

HELO
MAIL
RCPT
DATA
QUIT
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SieQ earned 250 total points
ID: 39975141
it seems that emails stuck with mail processing. I would first check the GFI logs for errors and in SMTP logs look for errors with numbers 400+ or 500+.
Next time don't reboot whole server.
First restart GFI services if it not solves then SMTP service, if it not helps IIS service and at the end the whole server.
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Assisted Solution

by:Enphyniti
Enphyniti earned 250 total points
ID: 39975144
When is the last time the system was restarted?  Any 2003 SMTP server I deploy gets a scheduled task to restart SMTP services every week.  I have fewer issues that way.

Were there any other issues on the system such as low disk space or high CPU or memory utilization?

If it happens again, I would first restart the SMTP service and check to see if mail is flowing.  If not, restart your GFI services, and see if that works.  That will tell you which is actually impeding mail flow and narrow down the possibilities to investigate.
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Author Comment

by:gopher_49
ID: 39975216
I had plenty of disk space, plenty of CPU, and plenty of memory.  In the past I would use the GFI stopsink.bat file to determine if GFI was the problem or not.  It's been almost a year since I've seen this..  I have not rebooted this server in about 2-3 months..  Maybe a little longer.
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Expert Comment

by:Enphyniti
ID: 39975236
In that case, I suggest selective service restarts as described, in whatever order you prefer next time you encounter an issue.  Whichever restart restores mail flow will identify your culprit.

At that time, you can decide if it's worth digging into further, or just schedule an automated service restart on a regular basis.
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Expert Comment

by:SieQ
ID: 39975382
Please review the GFI logs, for sure you'll find the answer for your problems there.
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Author Closing Comment

by:gopher_49
ID: 39975540
I'll take these steps next time..  Didn't have time to troubleshoot this time around.
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