Sendmail config behind proxy for sendmail 8.8 and newer

Sendmail 8.8 Config For UNIX Servers Behind A Proxy Server

This page is different from the standard 8.7 and earlier sendmail releases. In sendmail 8.8 there were many anti-spam rulesets added. There were also some changed configuration values, and names. Believe me, this made things a little bit tougher. This was kickin' my ass for about 48 hours, spread across a 2 week period. I am glad to have finally won this battle however. My findings follow :

Steps to execute (Example shown is for SCO UnixWare 7, version 7.0.1) :

First is always to find the current sendmail.cf file. We will need to copy it.

I always use "find / -name sendmail.cf -print" to find it. For UnixWare 7 it is in /etc.

cd /etc
It is no longer neccessary to move the resolv.conf to resolv.conf.hold, because the relay works as it should. This was probably just ignorance of sendmails features, on my part, in the earlier releases.
Modify the file called "service.switch" in the /etc directory to have the AutoConf option be NO. This is what tells sendmail to use local hosts file for nameserver search. (You could have it do DNS, but that serves no point, since a mail server outside the firewall sends the mail. We just need to be able to send it to that server). Add one line to the bottom of the file. The line should look like one of the two lines below :

hosts /etc/hosts
hosts files

cd /etc
cp sendmail.cf sendmail.cf.orig
launch a browser and connect to the sendmail configuration page on the web. (What a nice tool !!!!) Choose the following options on the page :

Choose sendmail version 8.8
Choose the advance setup (anyone who knows me, knows I always choose advanced or custom !!!)
Below are the options I chose on my configuration (behind smtp proxy server) :

Comment           : UnixWare7 advance setup for 8.8
O/S type          : unknown
Use masquerade as : paul@pluzzi.com (the email account on my smtp/proxy server)
Use smart_host    : ntserver (the name of my smtp/proxy server)
Forward all mail directly to hosts within our domain, $=m  ---> should be checked
Do not show table features                                 ---> should remain checked
Do not show misc. features, macros, and classes            ---> should remain checked
Include SMTP mailer                                        ---> should remain checked

Click on the download cf button, and download this to somewhere where you will be able to transfer it from, to get to your unix's /etc directory. This will be the base file we will use to edit.
Now you need to copy the "Mlocal" section from the original base distribution cf file, to the new cf file, and comment out the existing "Mlocal" section.
Now make sure the path to the aliases file shows /etc/mail/aliases not /etc/aliases
Set the timeout variable to 1day not 5 days as delivered (O Timeout.queuereturn).
Comment the section that allows root to be exposed, known as the CE class.
Now the fun stuff. There are three sections of the rulesets we need to modify. They are shown below:

# handle domain-specific masquerading
#####
#####  This is the From: section of the rewriting rules
#####
#####  Modified masquerading rules, because my masquerade contains
#####    a special host name, not just domain name.
#####
## R$* < @ $=M . > $*   $: $1 < @ $2 . @ $M > $3        convert masqueraded doms
## R$* < @ $=w . > $*   $: $1 < @ $2 . @ $M > $3
## R$* < @ *LOCAL* > $* $: $1 < @ $j . @ $M > $2
## R$* < @ $+ @ > $*    $: $1 < @ $2 > $3               $M is null
## R$* < @ $+ @ $+ > $* $: $1 < @ $3 . > $4             $M is not null
R$* < @ $=M . > $*      $: < $M  [$1 @ $2] > $3 convert masqueraded doms
R$* < @ $=w . > $*      $: < $M  [$1 @ $2] > $3
R$* < @ *LOCAL* > $*    $: $1 < $M > $2
R$* < @ $+ @ > $*       $: < $2 > $3                    $M is null
R$* < @ $+ @ $+ > $*    $: $1 < @ $3 . > $4             $M is not null
#####
#####  End of special From: rewriting section of the rules
#####

S94
#R$+                    $@ $>93 $1
#####
#####  This is the Return-Path section - modified as well
#####
## R$* < @ *LOCAL* > $* $: $1 < @ $j . > $2
R$* < @ *LOCAL* > $*    $: < $M > $2
#####
#####  End of the Return-Path: rewriting section of the rules
#####

S61
#####
#####  Modify the Return address as well.
#####
## R$* < @ $* > $*      $@ $1 < @ $2 > $3               already fully qualified
R$* < @ $* > $* $@ $1 < @ $2 > $3               already fully qualified
##### 
#####  End of the special Return: section of the rewriting rules
#####
R$+                     $@ $1 < @ *LOCAL* >             add local qualification

Save the config file
Now stop and restart the sendmail service :

/etc/rc2.d/P81sendmail stop
/etc/rc2.d/P81sendmail start

test using command line mail command. I use something like :

mail PaulALuz@aol.com - and include a test line.

Find out if the mail has left the mail queue by :

"mailq" or "sendmail -bp"

Client Side:

In the mail browser, in my case aol, launch the mail utility.
Check to see if you got any new mail, hopefully from the sendmail server just configured.

Currently cant send to a mail server inside the firewall, but will be working on that next.............

More to follow ....... strike that, fixed it. I have now loaded the Option Pak's version of Microsoft SMTP server on my NT server, which is my DNS and Proxy. It tries to deliver according to hosts files first, and if that fails, it goes over the firewall/proxy. This is working fantastically for me right now. Only drawback .... Option Pak breaks the Oracle Application Server 4.0, when used with Service Pak 4. Well, back to the drawing board for that one !!