Problem with sendmail to internal exchange server

[George Doller]

I am running sendmail 8.9.3 on HPUX 11.0, when I run to an outside address it works fine. When I try and run to my internal exchange server it says, connecting to nysmtp.company.com and eventually times out and defers. If I telnet to this nysmtp server with port 25 and send email I receive the message. Any ideas as to why I can send outside but not internal???? Thanks for any input.

[George Doller]

I made a mistake. If I telnet on port 25 it does NOT work.
Thanks

[Jordan Bean]

Connection refused? Or SMTP is accepted, but the message just evaporates? Have your Exchange admin ensure that the Internet Mail Service is enabled.

[George Doller]

The exact error is this:
Connecting to nysmtp.company.com via esmtp
connecting to nysmtp2.company.com via esmtp
Deferred: Connection timed out with nysmtp2.company.com

We do receive email from other places/people so I assume that internet services are on on the exchange server.

[Jordan Bean]

"Deferred:..." is a sendmail error message. What exactly happens with telnet to port 25? Does the nysmtp2 offer an esmtp greeting or it silent? How far along the esmtp transaction can you go?

You should get something like this:
$ telnet nysmtp2 smtp
Trying a.b.c.d...
Connected to nysmtp2.
Escape character is '^]'.
220 nysmtp2.company.com ESMTP Server (Microsoft Exchange Internet Mail Service 5.5.2653.13) ready
helo hpux.westaff.com
250 OK
mail from: <>
250 OK - mail from <>
rcpt to: gdollar@company.com
250 OK - Recipient
data
354 Send data. End with CRLF.CRLF
testing
.
250 OK
quit
221 closing connection
Connection closed by foreign host.
$

Also, just for yucks, could you report what sendmail -bv gdollar@company.com says?

[George Doller]

I get the same response that you provided when I do telnet nysmtp.company.com 25 but I never get the mail message in exchange. When I do the sendmail -bv gdoller@company.com I get the following:
gdoller@company.com... deliverable: mailer esmtp, host company.com., user gdoller@company.com

I hope this gives you the info. you were looking for.

[Jordan Bean]

You didn't get the message? Hold that thought. I still want to look at sendmail. In /etc/mail/sendmail.cf, are DS, DH, DR, and DM (if masquerading is desired) all set to $m or company.com (which forces sendmail to resolve MX hosts via DNS for the domain)? Is the sendmail host able to resolve via DNS? Is it finding nysmtp2 correctly?

[George Doller]

I am using a vanilla sendmail.cf (no changes). Yes I can do an nslookup and find nysmtp and nysmtp2 addresses. Just a reminder, I can sendmail to anywhere outside of my company, but just not to my exchange server.

[Jordan Bean]

I'm stumped at the moment (too many other things on my mind, I guess) and I fear that there is something obvious at which I should be looking. You can send to anywhere but Exchange... the connection is timing out... The message you sent via telnet disappeared... Is Exchange griping about anything? You might find more useful information by searching for previous posts on this subject.