Sendmail Masquerading (Error 553)

Sendmail Masquerading (Error 553)

Post by Dave Shawle » Mon, 03 Dec 2001 15:55:32

Hello all,

I have a Sendmail configuration question... I had masquerading working
under FreeBSD 4.2 but forgot to backup my configuration files when I
went to FreeBSD 4.4 and needless to say I can't remember the exact
incantations that I had to put in my mc file.

Anyway, here is my current situation. I have placed the following in
my /etc/mail/ file:

define(`SMART_HOST', `')

My intent is to rewrite the envelope headers so that mailers that are
smart enough to do DNS lookups to cough at my mail. My external
address is (well just assume that) and
my internal net is ``'' (at if that matters).
I'm not sure if I need the MASQUERADE_EXCEPTION or not but it doesn't
seem to help if I remove it and if I remember correctly I need it to
make local mail work. Heres the version information from my installed

isengard$ telnet localhost smtp
Trying ::1...
Connected to localhost.
Escape character is '^]'.
220 ESMTP Sendmail 8.11.6/8.11.6; Sun, 2 Dec 2001
01:39:40 -0500 (EST)
221 2.0.0 closing connection
Connection closed by foreign host.

And here is a transcript from a failed outgoing mail session:

   ----- The following addresses had permanent fatal errors -----

    (reason: 553 does not exist)

   ----- Transcript of session follows -----
... while talking to
<<< 553 does not exist
501 5.6.0 Data format error

local address is in the envelope. I've tried faking it out by using
a ``From'' line in my mail message but that doesn't seem to do the
job. I remember having to add some ``Reply To'' lines in my NMH
composition stuff... I haven't done that yet but I don't think that
it is the issue here. I can send mail by telneting to my relay and

line so it looks like if I can get Sendmail to rewrite the envelope
correctly I should be set.

Can anyone give me a hand here?

Thanks in advance...

- Dave Shawley


Sendmail Masquerading (Error 553)

Post by Claus A?man » Tue, 04 Dec 2001 05:48:22

> define(`SMART_HOST', `')
> FEATURE(`masquerade_envelope')
> ... while talking to



from your .mc file, generate a new .cf file, and install it.

Then try again.

Quoting cf/README:
To exempt hosts or subdomains from being masqueraded, you can use

If you feel the urgent wish to send me a courtesy copy of a Usenet
posting, then make sure it's recognizable as such!
The FAQ:              Before you ask.


1. 2.2 sendmail: 553 host name configuration error

Okay folks, sorry if it's a FAQ, but this has been bugging me quite
a bit...
What's up with this:

16:28:36 - 113 #...; /usr/lib/sendmail -v jmason

Now, shouldn't a command-line invocation of /usr/lib/sendmail try to
deliver locally without trying to connect to its OWN port 25, or at
least try and connect to the real mailhost, or even to's
MX-record host? Why is it so brain-damaged??! :(

I've applied the 101077-03 jumbo sendmail patch, and the same thing
happens with both and I'm stumped. The -bt 3,0
ruleset testing works grand, and the rewriting is valid... mail from
other hosts works grand too. It's only local mail-sending that's stuck.

Anyone know?
Justin Mason  (Iona Technologies' unix caretaker, fixer-upper and disk-filler)

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