Howdy, all.

I have a little problem I'm trying to troubleshoot, and am having difficulty finding 
info on it.

I have set up IIS5 on a Win2kPro (SP2, fully patched) box that's destined to sit in my 
DMZ, and act as a relay box for our Exchange server.

I'm currently testing it before deploying it, and have run into problems getting it to 
talk with several domains, including msn.com and attbi.com. Other domains have no 
problems. It's not a reverse DNS lookup issue, since switching my outbound SMTP server 
to the linux/sendmail box that I'm about to decomnission uses the same IP address and 
has no problems.

I'm testing with a friend at another company, and I get a delivery status notifcation 
(failure) message, with an attachment that reads as follows:
___________________________________
Reporting-MTA: dns;mycompany.com
Arrival-Date: Thu, 20 Dec 2001 13:03:31 -0800

Final-Recipient: rfc822;[EMAIL PROTECTED]
Action: failed
Status: 5.0.0
Diagnostic-Code: smtp;500 Syntax error, command unrecognized
er OK
0-TURN
250-ATRN
250-SIZE
250-ETRN
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-VRFY
250-X-LINK2STATE
250-XEXCH50
250 OK
___________________________________________

The logs from his Exchange 2000 server are in this form:

date time c-ip cs-username s-sitename s-computername s-ip s-port cs-method cs-uri-stem 
cs-uri-query sc-status sc-win32-status sc-bytes cs-bytes time-taken cs-version cs-host 
cs(User-Agent) cs(Cookie) cs(Referer) 
2001-12-20 22:52:09 216.202.42.5 mycompany.com SMTPSVC1 MERCURY 192.168.11.2 0 EHLO - 
+mycompany.com 250 0 228 15 110 SMTP - - - -
2001-12-20 22:52:09 216.202.42.5 mycompany.com SMTPSVC1 MERCURY 192.168.11.2 0 MAIL - 
+FROM:<[EMAIL PROTECTED]> 250 0 47 34 47 SMTP - - - -
2001-12-20 22:52:09 216.202.42.5 mycompany.com SMTPSVC1 MERCURY 192.168.11.2 0 RCPT - 
+TO:<[EMAIL PROTECTED]> 250 0 28 25 0 SMTP - - - -
2001-12-20 22:52:09 216.202.42.5 mycompany.com SMTPSVC1 MERCURY 192.168.11.2 0 QUIT - 
mycompany.com 0 547 67 4 0 SMTP - - - -

I'm using my personal laptop with Outlook2000 to send the message, and the outbound 
SMTP is the new relay server.

I've set the domain in the default virtual server on IIS5 so that it's supposed to be 
using HELO instead of EHLO, but the logs on the Exchange 2000 server at his end 
(hiscompany.com) indicate that the SMTP service on my end is still using EHLO.

I've googled and searched support.microsoft.com for clues, to no avail. Has anyone run 
into this issue?


Kurt




Passwords are like underwear: you don't share them, you don't hang them on your 
monitor, or under your keyboard, you don't email them, or put them on a web site, and 
you must change them very often. - Sunder 


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