iis smtp service messages stuck in queue

[hug...@yahoo.com]

When I try to send email from the smtp service in iis on my workstation
the messges get stuck in the queue. The even log shows ID 4000
Message delivery to the remote domain 'hotmail.com' failed for the
following reason: The connection was dropped by the remote host.

This occurs whether I'm trying to send to an outside address as above
or to an account on my exchange server. This behaviour began after I
migrated from Exchange 2000 to Exchange 2003. We also upgraded AD to
2003 at this time.

Thanks for your help,
Hugh

[Gustavo Del Grosso]

Did you test name resolution? can you find hotmail.com using nslookup on the
exchange server?
Can you relay mails using telnet to the exchange server on port 25?
--
Gustavo Del Grosso
Laboratorios Andrómaco
Gerencia de Tecnología
gustavod...@hotmail.com

[hug...@yahoo.com]

The exchange server is not having any problems sending or receiving
mail. The probelm exists when trying to send email directly from the
smtp service on our workstations.

In other words I have no problem sending and receiving email from
outlook but when I telnet into my local (127.0.0.1) smtp server the
messages get stuck in the queue.

When I do an nslookup on our workstations I get
C:\Documents and Settings\hcaldwell\My Documents>nslookup
agmail2.arlgroup.com
Server: agdc1.aginside.com
Address: 192.168.100.21

Name: agmail2.arlgroup.com
Address: 192.168.100.26

Nslookup from our DMZ returns:
Non-authoritative answer:
Name: agmail2.arlgroup.com
Address: 208.255.172.189

Nslookup from the server at my house returns:
C:\Documents and Settings\Administrator>nslookup agmail2.arlgroup.com
Server: riderserv01.riders.local
Address: 10.0.0.1

Non-authoritative answer:
Name: agmail2.arlgroup.com
Address: 208.255.172.189

All of the emails in our dmz are getting stuck in the queue also. The
email I sent by telneting into the smtp service on my home server
delivered the mail without a problem.

thanks,
Hugh

[hug...@yahoo.com]

Here are the typical contents of my smtp log file
6:05:46 - - - 0
16:05:46 mc10-f26.hotmail.com EHLO - 0
16:05:47 mc10-f26.hotmail.com - - 0
16:05:47 mc10-f26.hotmail.com MAIL - 0
16:05:47 mc10-f26.hotmail.com - - 0
16:05:47 mc10-f26.hotmail.com RCPT - 0
16:05:49 mc10-f26.hotmail.com - - 0
16:05:49 mc10-f26.hotmail.com BDAT - 0
16:06:24 - - - 0
16:06:24 mc2-f23.hotmail.com EHLO - 0
16:06:25 mc2-f23.hotmail.com - - 0
16:06:25 mc2-f23.hotmail.com MAIL - 0
16:06:25 mc2-f23.hotmail.com - - 0
16:06:25 mc2-f23.hotmail.com RCPT - 0
16:06:28 mc2-f23.hotmail.com - - 0
16:06:28 mc2-f23.hotmail.com BDAT - 0
16:06:59 agmail2.arlgroup.com - - 0
16:06:59 agmail2.arlgroup.com RSET - 0
16:06:59 agmail2.arlgroup.com QUIT - 0
16:08:59 - - - 0
16:08:59 agmail2.arlgroup.com EHLO - 0
16:08:59 agmail2.arlgroup.com - - 0
16:08:59 agmail2.arlgroup.com MAIL - 0
16:08:59 agmail2.arlgroup.com - - 0
16:08:59 agmail2.arlgroup.com RCPT - 0
16:08:59 agmail2.arlgroup.com - - 0
16:08:59 agmail2.arlgroup.com BDAT - 0
16:19:02 agmail2.arlgroup.com - - 0
16:19:02 agmail2.arlgroup.com RSET - 0
16:19:02 agmail2.arlgroup.com QUIT - 0
16:21:02 - - - 0

thanks,
Hugh

[Steve Manatt]

Try adding the IP address of the web server in the Relay Restrictions of its
SMTP server. In other words,

Say the IIS Server that sends the e-mail has an IP address of
192.168.168.25.

1. Go to the IIS Admin MMC ~ the SMTP Server properties ~ Access
~ Relay
2. Choose "Only the list below" and add 19.168.168.25 to the list
3. Leave bottom checkbox checked that talks about authenticated users
4. Hit OK and mail should immediately be delivered

Hope this helps, this just worked for me and I have been battling the same
scenario you described for the past 6 days.