I have a situation that I've come across from time to time that I have
never found a good fix for.

Sometimes I'll install a freebsd box at a site with private  addresses
(RFC 1918).  Most of the time these sites also have local DNS setups.

I'll take my home network as an example.  My FreeBSD box (7.2) does:
 - File serving
 - PPP/Routing/NATd for the local network
 - WWW
 - Local DNS

Nothing special.
The network is a 192.168 network and the local domain is .lan

The problem is when I try to forward periodic output to my real email
address.  My email box see's the EHLO from beastie.lan and rejects the
message based on the fact that r...@beastie.lan is an unroutable address.

There are a few solutions I've used in the past.
 - Replace sendmail with exim and configure the SMTP domain.
 - Put beastie.lan in my email servers hosts file.

Neither of these are what I am looking for.  I'd like to make sendmail
re-write all outgoing emails (envelope as well as message) as
*...@some.real.domain instead of *...@beastie.lan.

I have a simple sendmail submit setup.  (sendmail=no in rc.conf)

I've added the following to the default sendmail mc file:

MASQUERADE_AS(`mypublicdomain.com')dnl
FEATURE(masquerade_envelope)dnl
MASQUERADE_DOMAIN(beasie.lan)dnl

Recompiled the cf files and restarted sendmail.

Here is the kicker.  If I log in as a normal user it masquerades just
fine.

If I simply "su -"  to root, the masquerading works fine and the mail is
sent as the original logged in user.

But if I log in as root via the console then it does not alter the messages.

Apart from ditching sendmail for another MTA, does anyone know how I
might coerce sendmail into rewriting root's messages as well?
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