If I execute it using the Terminal, I do the following steps:

• 1) Open DOSBox application package by right-clicking, choosing "Show package content"
  2) Browse to "Contents/MacOS/DOSBox"
  3) Drag the DOSBox unix executable onto the Terminal window
  4) add "-conf " to the line, by typing it
  5) Locate the custom configuration file, dragging it onto the Terminal window as well
  6) Press return to execute the command line.

😉

But it seems on first glance to be using the correct conf...

are you allowed to open port 23 ? root access ? firewall ?

i am new to the mac, how would you open port 23 with root access. I do know that my MAC firewall is disabled. I did a check in the terminal and it shows all ports are open from any IP address.

i launched DOSBOX via the show package contents for the MAC and in the terminal it shows that "Serial1: Modem could not open TCP port 23." I have checked the terminal to find out what ports are open.

Dosbox shows:

Last login: Wed Feb 6 17:06:04 on ttys001
mymac:~ chrisschneider$ /Applications/DOSBox.app/Contents/MacOS/DOSBox ; exit;
DOSBox version 0.74
Copyright 2002-2010 DOSBox Team, published under GNU GPL.
---
CONFIG:Loading primary settings from config file dosbox.conf
MIDI:Opened device:coreaudio
Serial1: Modem could not open TCP port 23.

Terminal shows the below for ports opened:

mymac:~ chrisschneider$ sudo ipfw list
65535 allow ip from any to any

> sudo ipfw list

and without sudo? Also, try a different port number like 1023. If that works, you don't have the right for low port numbers or maybe there is already something else using this port.

Or try running dosbox with sudo

Tried to run DOSBox with sudo and I still get the error in the terminal stating "Serial1: Modem could not open TCP port 23."

Well then try hals ideas 😉

Thought I replied for Hals idea already. Same error even on higher ports.

I got it working. even though port 1023 did not work, i boosted it to port 5000 and it worked. Not sure why i cannot get this mac to listen on port 23 though..
I am still open to suggestions.

Probably what hal wrote...

Ports from 1024 down are protected, only services and root can open them.

Running dosbox with sudo should have fixed it though:

1squallstrife-mbp:MacOS squallstrife$ ./DOSBox 
2DOSBox version 0.74
3Copyright 2002-2010 DOSBox Team, published under GNU GPL.
4---
5CONFIG:Loading primary settings from config file /Users/squallstrife/Library/Preferences/DOSBox 0.74 Preferences
6MIDI:Opened device:coreaudio
7Serial1: Modem could not open TCP port 23.
8^C
9
10squallstrife-mbp:MacOS squallstrife$ sudo ./DOSBox 
11Password:
12DOSBox version 0.74
13Copyright 2002-2010 DOSBox Team, published under GNU GPL.
14---
15CONFIG:Loading primary settings from config file /Users/squallstrife/Library/Preferences/DOSBox 0.74 Preferences
16MIDI:Opened device:coreaudio
17Serial1: Modem listening on port 23...