1. fix the command search path

echo '
export PATH="/usr/local/bin:/usr/local/sbin:/usr/local/lib:/usr/local/include:/usr/bin:/bin:/usr/sbin:/sbin"
' >> $HOME/.bash_login

source $HOME/.bash_login

2. upgrade Postfix

# first make a backup of the entire /private/etc/postfix directory
sudo /usr/bin/ditto -rsrc -c -k /private/etc/postfix "/private/etc/postfixdir-$(/bin/date "+%Y-%m-%d-%H.%M.%S").zip"

cd ~/Desktop
curl -L -O http://mirrors.isc.org/pub/postfix/official/postfix-2.5.0.tar.gz
tar -xzf postfix-2.5.0.tar.gz
cd postfix-2.5.0

# make -h


# cf. http://www.postfix.org/TLS_README.html
# requires Xcode, http://developer.apple.com/tools/download/

find /usr -type f \( -name "libcrypto*" -or -name "libssl*" \) -print0 2>/dev/null | xargs -0 ls -l

make makefiles \
   CFLAGS='-arch $(/usr/bin/arch) -isysroot /Developer/SDKs/MacOSX10.4u.sdk' \
   CCARGS="-DUSE_TLS" \
   AUXLIBS="-lssl.0.9.7 -lcrypto.0.9.7"


make

# sudo make install
# or
sudo make upgrade

3. remove comments & empty lines from /private/etc/postfix/main.cf

sudo cp -p /private/etc/postfix/main.cf /private/etc/postfix/main.cf.orig   # backup
sudo sed -i "" -e 's/^[[:space:]]*#.*$//g' -e '/^[[:space:]]*$/d' /private/etc/postfix/main.cf
sudo nano /etc/postfix/main.cf

4. create a new Postfix launch daemon

# backup
sudo cp -p /System/Library/LaunchDaemons/org.postfix.master.plist /System/Library/LaunchDaemons/org.postfix.master.plist.orig  

sudo nano /System/Library/LaunchDaemons/org.postfix.master.plist

<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE plist PUBLIC "-//Apple Computer//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
<plist version="1.0">
<dict>
	<key>Disabled</key>
	<true/>
	<key>Label</key>
	<string>org.postfix.master</string>
	<key>OnDemand</key>
	<false/>
	<key>Program</key>
	<string>/usr/libexec/postfix/master</string>
	<key>ProgramArguments</key>
	<array>
		<string>master</string>
	</array>
	<key>QueueDirectories</key>
	<array>
		<string>/var/spool/postfix/maildrop</string>
	</array>
</dict>
</plist>


sudo launchctl load -w /System/Library/LaunchDaemons/org.postfix.master.plist 2>/dev/null
#sudo launchctl unload -w /System/Library/LaunchDaemons/org.postfix.master.plist 2>/dev/null

5. initialize the configuration

sudo mv /private/etc/postfix/master.cf /private/etc/postfix/master.cf.orig
sudo cp -p /private/etc/postfix/master.cf.defaultserver /private/etc/postfix/master.cf

sudo nano /private/etc/postfix/master.cf
# uncomment the following line if necessary
#smtp      inet  n       -       n       -       -       smtpd     

sudo /usr/sbin/postfix reload

6. test

sudo ln -s "/Applications/Utilities/Network Utility.app/Contents/Resources/stroke" /bin/portscan
portscan localhost 25  25     #  Open TCP Port:  25  smtp

/usr/sbin/postconf -d | grep 'mail_version ='

sudo postfix check
sudo postfix status
#sudo postfix -vv status

open -a Console   # see /private/var/log/mail.log

dscl . -read /Users/postfix
dscl . -read /Groups/postfix
dscl . -read /Groups/postdrop
dscl . list /Groups GroupMembership

otool -Lv /usr/libexec/postfix/smtp       # libssl & libcrypto
otool -Lv /usr/libexec/postfix/smtpd
otool -Lv $(/usr/sbin/postconf -h daemon_directory)/smtpd


# send a mail 
echo 'hello world' | mail -s 'test mail' $(/usr/bin/logname)@localhost
mail   # quit with "q <return>"

# send a mail via telnet

your_logname="$(/usr/bin/logname)"
echo $your_logname

telnet localhost 25
<...>
helo localhost
<...>
ehlo localhost
<...>
mail from:<your_logname>@localhost
<...>
rcpt to:<your_lognam>@localhost
<...>
data
<...>
subject: something
my message
.
<...>
quit

mail

Further information:

- Postfix Installation From Source Code
- Postfix Basic Configuration
- Postfix TLS Support
- Postfix on Mac OS X
- Troubleshooting Postfix
- DIYMacServer