Configure postfix as relay for OS X

macosx-configure-postfix-as-relay.md

Configure postfix as relay for macOS Sierra – Sonoma

• Source: http://www.developerfiles.com/how-to-send-emails-from-localhost-mac-os-x-el-capitan/
• Source: http://budiirawan.com/install-mail-server-mac-osx/
• Source: https://apple.stackexchange.com/questions/32228/whats-the-correctly-way-to-make-postfix-run-permanently-on-lion-not-server

1. Edit postfix configuration file

1. sudo vi /etc/postfix/main.cf
2. Ensure that the following values are set:

   mail_owner = _postfix
   setgid_group = _postdrop
   

3. Add the following lines at the end of the file:

   # Postfix as relay
   #
   #Gmail SMTP
   relayhost=smtp.gmail.com:587
   #Hotmail SMTP
   #relayhost=smtp.live.com:587
   #Yahoo SMTP
   #relayhost=smtp.mail.yahoo.com:465
   # Enable SASL authentication in the Postfix SMTP client.
   smtp_sasl_auth_enable=yes
   smtp_sasl_password_maps=hash:/etc/postfix/sasl_passwd
   smtp_sasl_security_options=noanonymous
   smtp_sasl_mechanism_filter=plain
   # Enable Transport Layer Security (TLS), i.e. SSL.
   smtp_use_tls=yes
   smtp_tls_security_level=encrypt
   tls_random_source=dev:/dev/urandom
   

2. Create sasl_passwd file

1. sudo sh -c 'echo "\nsmtp.gmail.com:587 [email protected]:your_password" >> /etc/postfix/sasl_passwd' Replace [email protected] and your_password with actual values.
2. sudo postmap /etc/postfix/sasl_passwd

3. Autorun postfix on boot and restart postfix

1. Copy the postfix master plist out of System folder.

   sudo cp /System/Library/LaunchDaemons/com.apple.postfix.master.plist /Library/LaunchDaemons/org.postfix.custom.plist
   

2. sudo vi /Library/LaunchDaemons/org.postfix.custom.plist

3. Change the label value from com.apple.postfix.master to org.postfix.custom

   Remove these lines to prevent exiting after 60s

     <string>-e</string>
     <string>60</string>
   

   Add these lines before </dict>

     <key>KeepAlive</key>
     <true/>
     <key>RunAtLoad</key>
     <true/>
   

4. Relaunch the daemon.

   sudo launchctl unload /Library/LaunchDaemons/org.postfix.custom.plist
   sudo launchctl load /Library/LaunchDaemons/org.postfix.custom.plist
   

5. Check that daemon has started.

   sudo launchctl list | grep org.postfix
   

4. Turn on less secure apps for gmail

In Gmail we must switch on the option "Access for less secure apps", otherwise we will get the error: SASL authentication failed

5. Test

1. echo "Test sending email from Postfix" | mail -s "Test Postfix" [email protected]

   Change [email protected] with valid email with mailbox access for easy checking.

2. Check mail queue and possible delivery errors with mailq.

3. Check mail log with tail -f /var/log/mail.log.

mutt is working via shell, but not with my php.mail() function
is there any additional settings to do or maybe in mamp pro conf or in php.ini file?
thank you for your help david

hello @dfkotz
I have explored many solutions and now, i think i could know more about the problem,
i have this error message
(Cannot start TLS: handshake failure)
any advice pease??

Thanks @dfkotz my gmail is working it in Monterey!