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emails stuck in IIS SMTP queue - relay to Exchange 2010

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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gopher_49
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gopher_49
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2 Solutions
 
SieQCommented:
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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Jon BrelieSystem ArchitectCommented:
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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gopher_49Author Commented:
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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SieQCommented:
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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Jon BrelieSystem ArchitectCommented:
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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gopher_49Author Commented:
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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Jon BrelieSystem ArchitectCommented:
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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SieQCommented:
Please review the GFI logs, for sure you'll find the answer for your problems there.
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gopher_49Author Commented:
I'll take these steps next time..  Didn't have time to troubleshoot this time around.
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