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Date:      Sun, 20 May 2001 23:18:00 -0500
From:      Andrew Hesford <ajh3@usrlib.org>
To:        Giorgos Keramidas <keramidi@otenet.gr>
Cc:        Munish Chopra <messiah_man@hotmail.com>, freebsd-questions@FreeBSD.ORG
Subject:   Re: mutt/sendmail/SMTP trouble
Message-ID:  <20010520231800.B87357@core.usrlib.org>
In-Reply-To: <20010521070130.A11649@hades.hell.gr>; from keramidi@otenet.gr on Mon, May 21, 2001 at 07:01:31AM %2B0300
References:  <F885kcDj6QqW9F0qnqE00015006@hotmail.com> <20010521070130.A11649@hades.hell.gr>

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On Mon, May 21, 2001 at 07:01:31AM +0300, Giorgos Keramidas wrote:
> On Sun, May 20, 2001 at 01:08:53PM +0200, Munish Chopra wrote:
> > I finally thought I had mutt handing my outgoing mail to sendmail, which 
> > would hand it over to an SMTP-server. I'm not sure where things are going 
> > wrong, but whenever I send a mail to a server that does reverse DNS, I get 
> > the following:

It is not reverse DNS, just a regular DNS query. The problem is that
messiah.megadeb.org does not have a corresponding IP address, as far as
bsd-dk.dk is concerned. If messiah is a new host, you might need to wait
for the DNS cache at bsd-dk.dk to expire. Or, you might not even have an
A record for messiah.

I had this problem with usrlib.org. My host is called core.usrlib.org,
and I couldn't send mail to freebsd.org without configuring postfix to
call itself usrlib.org. This was because freebsd.org had cached a bad
copy of my DNS information, and it took a few days to expire.
Ultimately, it did, and I am now able to send mail from core.usrlib.org
without any hostname tricks.

The receiving mailserver simply wants to make sure your domain isn't
fake... it complains when a DNS lookup of messiah.megadeb.org fails. If
you've changed things, wait; otherwise you probably have a misconfigured
DNS server.

> > ---snip---
> > 
> > [-- Type: message/delivery-status, Encoding: 7bit, Size: 0.4K --]
> > 
> > Reporting-MTA: dns; messiah.megadeb.org
> > Arrival-Date: Sun, 20 May 2001 12:56:10 +0200 (CEST)
> > 
> > Final-Recipient: RFC822; majordomo@bsd-dk.dk
> > Action: failed
> > Status: 5.1.8
> > Diagnostic-Code: SMTP; 501 5.1.8 <messiah@messiah.megadeb.org>... Domain of
> > +sender address messiah@messiah.megadeb.org does not exist
> > Last-Attempt-Date: Sun, 20 May 2001 12:56:13 +0200 (CEST)
> 
> You have to set Sendmail up to masquerade outgoing mail to have
> an 'envelope from' address from a domain that *does* resolve properly.
> 
> There are many ways to do this.  One of them, that will masquerade ALL
> messages sent from your local Sendmail to an outgoing SMTP is to add to your
> master-config the macros:
> 
>     MASQUERADE_AS(`some.domain')dnl
>     FEATURE(`masquerade_entire_domain')dnl
>     FEATURE(`masquerade_envelope')dnl
> 
> Then, after the usual sendmail.cf generate, copy to /etc/mail, and restart of
> Sendmail, all the mail going out will be seen as coming from `some.domain'.
> A good choise for `some.domain' is the domain of your ISP.
> 
> Another quick way of handling this is to set your MUA up to call sendmail with
> the -f option, and masquerade all the mail sent from this MUA as coming from
> some valid user@domain address.  For instance, I had in my .muttrc for quite
> some time the following:
> 
>     set sendmail="/usr/sbin/sendmail -oem -oi -f keramidi@otenet.gr"
> 
> Where `keramidi@otenet.gr' is my normal mailbox address at my ISP's mail
> servers.  This works like a charm, but you might need to add your local
> account to the `trusted users' class of Sendmail to inhibit the automatic
> generation of an `X-Authentication-Warning' header (which is automagically
> inserted in the outgoing mail headers by Sendmail, if some non-trusted user
> fires up Sendmail with the -f option to change their envelope from address).
> 
> --giorgos

Masquerading was designed so that multiple mailservers in one domain
could be recognized as a single domain entity, e.g., mail1.freebsd.org
and mail2.freebsd.org both look and act like freebsd.org.

It is bad form to masquerade as a domain you do not control. In
addition, it can be confusing and misleading to people sifting through
headers. It makes mail appear to come from, say, your ISP, when in fact
it is totally unrelated to your ISP.

If he does any masquerading, it should be as megadeb.org and nothing
else. However, a masquerading mail server is no substitute for properly
configured DNS and mail servers.

-- 
Andrew Hesford
ajh3@usrlib.org

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