sendmail/DNS problem in FreeBSD 5

[Michael Dale]

I recently did a reinstall of FreeBSD on my web server (hard drive died) 
and I decided to upgrade from 4.11 to 5.4.

Anyway everything is working fine except for this odd sendmail issue.

So the info. I have two servers.
10.0.0.1:extranet.dalegroup.net: DNS and Mail (Windows 2003)
10.0.0.3:metro.dalegroup.net: Web Server (FreeBSD 5.4-Release, with 
sendmail)

The web server box points to extranet for DNS.

Now for my domain the internal setup is that the MX record for 
dalegroup.net points to extranet.dalegroup.net. Which is fine.

But whenever I send mail from the web server to say 
someuser at dalegroup.net it cannot do a lookup.

Jul 20 21:35:23 metro sm-mta[34324]: j6KBZNrb034322: 
to=<someuser at dalegroup.net>,
ctladdr=<mwdmeyer at metro.dalegroup.net> (1001/0), delay=00:00:00,
xdelay=00:00:00, mailer=esmtp, pri=30378,
elay=extranet.dalegroup.net., dsn=4.0.0, stat=Deferred: Name server:
extranet.dalegroup.net.: host name lookup failure

but if I do this:

metro# dig dalegroup.net MX

;; QUESTION SECTION:
;dalegroup.net. IN MX

;; ANSWER SECTION:
dalegroup.net. 3600 IN MX 10 extranet.dalegroup.net.

;; ADDITIONAL SECTION:
extranet.dalegroup.net. 3600 IN A 10.0.0.1

;; Query time: 2 msec
;; SERVER: 10.0.0.1#53(10.0.0.1)
;; WHEN: Wed Jul 20 21:48:55 2005
;; MSG SIZE rcvd: 159

It is fine! Sendmail doesn't seem to want to send to the dalegroup.net 
domain, or the domain it is part of.

If I modify the DNS and have my MX record on dalegroup.net to point to 
extranet.dalegroup.ORG (different domain, points to same IP) it works.

Ideas?! Thanks :)

P.S I didn't have this problem on FreeBSD 4.11. Sendmail hasn't be 
touched. Also some other info:

metro# cat resolv.conf
domain dalegroup.net
nameserver 10.0.0.1

metro# cat hosts
::1 localhost.dalegroup.net localhost
127.0.0.1 localhost.dalegroup.net localhost
10.0.0.3 metro.dalegroup.net metro
10.0.0.3 metro.dalegroup.net.

-- 
Michael Dale