Need Unix help configuring SENDMAIL (MacOS X) as SMTP for 192.168.x.xxx boxes @ work

Factual Questions
1

Backdrop:

We are a small company without a huge IT department, and somebody decided it would be a good idea to install Exchange Server in replacement for the company’s mailserver. I’m a Eudora user and they can’t get Exchange Server working so that I can send email to folks outside the company. (Folks using Outlook are not having this problem. It’s a low priority for them because I’m the only person affected at the moment). I asked if they had any objections if I set up sendmail on a MacOS X box I’m using as webserver and used that as my SMTP and they said go ahead, and I’m less busy than they are at the moment.

/Backdrop

Situation:

I have sendmail working on the MacOS X box itself. I can open Eudora there and send outbound mail with no issues. The computer I use as a workstation, though, is a PowerBook with MacOS 9. Depending on where I plug it in, the PowerBook has an internal behind- the- NAT- &- firewall IP of either 192.168.1.105 or 192.168.4.105 (I can run OS X on it and in that mode can send mail from the PowerBook using its own sendmail, but I need to remain in 9 on a regular basis for the time being). When I reference the OS X box as my SMTP server, the OS X box refuses to send my outbound email, replying back “relaying denied”.

There appear to be three editable configuration files on the OS X box where changes would have a favorable effect on this problem, but I can’t seem to get it working.

a) In /usr/share/sendmail/conf/cf are some “mc” files, among which is generic-darwin.mc, which I copied and edited so as to include some additional instructions (my modifications in bold):

The “dont_blame_sendmail” is supposed to override sendmail’s irritability about some directories being group-writable, which they are under OS X but not BSD Unix. The relay_mail_from is a very non-conservative and non-cautious instruction to relay the freakin’ mail when the PowerBook asks it to.

b) In /etc/mail is a file called access.db which is created from another file simply called “access” in the same folder. The “access” file is user-editable text, and I have added relay instructions as follows:

c) in /etc there is a file called hosts, and I have added the following to the hosts file:

Despite these things, which according to my research ought to result in the OS X box doing for the PowerBook what it does for itself with sendmail, I still get email stuck in the Out box with a red “X” and the error message “relaying denied”.

I’ve been seeking help on the MacOS X Hints forum to no avail (or to no successful avail at any rate).

PS–don’t suggest switching from Eudora. Not an option.

2

… I did build the access.db file from the text “access” file using sudo makemap hash /etc/mail/access > /etc/mail/access, and I also did construct the m4 file from the clone of generic-darwin.mc using m4 …/m4/cf.m4 mymodifiedfile.mc > /tmp/sendmail.cf followed by sudo cp /etc/mail/sendmail.cf /etc/mail/sendmail.cf.orig to backup the original and sudo cp /tmp/sendmail.cf /etc/mail/ to install the version of sendmail.cf I’d created as the live copy. And I restarted the computer and verified that sendmail was working locally correctly. I realize I didn’t mention that I’d done those things. You should not assume that I didn’t leave out something just as basic, through, I probably did.

3

Well, I’m now being told that I should not be using ‘makemap’ and should be using ‘newaliases’ instead. FWIW.

4

Sendmail is poweful, but infamously insecure. It sounds like you don’t need anything that fancy. I’d recommend Qmail or Postfix. The later has Sendmail-like configuration. Put simply, if you need help with Sendmail, you shouldn’t be using it to begin with, because you’re gonna get 0wn3d real soon. Don’t take that as an insult, there are very few system administrators who have the necessary Godlike anti-hacker know-how for Sendmail.

UnuMondo

5

Are they mutually compatible? I’ve got sendmail working locally on the box and I’m sort of reluctant to yank it out in order to try out postfix or qmail.

6

Hooray, thanks to the geeks on MacOS X Hints, it’s working. I was apparently on the right track but I had not run makemap on the access file after redoing the access file. Or something. Actually I’m going to have to print out the thread and try to make some sense out of what was done in what order and why it finally worked. But it works and I’m using sendmail and I’m deploying it as SMTP server from a different computer and I’m not running it as an open relay.
http://forums.macosxhints.com/showthread.php?s=&postid=68326#post68326