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@kany
Last active June 3, 2024 20:13
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Setup SENDMAIL on Mac OSX Yosemite

SENDMAIL on MAC OSX Yosemite

  1. Create a file to store our credentials:
sudo vim /etc/postfix/sasl_passwd
  1. Add something like this:
smtp.gmail.com:587 username@gmail.com:password
  1. Now run:
sudo postmap /etc/postfix/sasl_passwd
  1. Prepare the postfix main config file:
sudo vim /etc/postfix/main.cf
  1. Add/update these lines
    relayhost=smtp.gmail.com:587
    smtp_sasl_auth_enable=yes
    smtp_sasl_password_maps=hash:/etc/postfix/sasl_passwd
    smtp_use_tls=yes
    smtp_tls_security_level=encrypt
    tls_random_source=dev:/dev/urandom
    smtp_sasl_security_options = noanonymous
    smtp_always_send_ehlo = yes
    smtp_sasl_mechanism_filter = plain
  1. Stop/Start the service
sudo postfix stop && sudo postfix start
  1. Check the queue for any errors
mailq
@rdermer
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rdermer commented Apr 18, 2020

Thanks for this - it was really helpful. Took a bit and eventually I got sendmail to work. For my ISP things didn't work until I added to /etc/postfix/main.cf - sendmail didn't want to connect using the resolved IPV6 addr.

net_protocols=ipv4

I also added this (not sure if this was needed -- the default value was loopback-only which looked suspicious).

inet_interfaces = all

For my google account I have 2FA enabled and needed an application specific password in /etc/postfix/sasl_passwd see https://support.google.com/accounts/answer/185833

Hope that helps someone else in getting this working.

@ivan-gloginjic
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Works :-) thanks

@kingnight
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I also have the problem TLS is required, but our TLS engine is unavailable, then modify sudo vim /etc/postfix/main.cf change
smtp_tls_security_level=none,problem fix

@ddaddy
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ddaddy commented Feb 19, 2021

I'm having issues with Xcode server bot sending emails. I get these logs:

kernel    Sandbox: sendmail(48548) deny(1) forbidden-exec-sugid
sendmail    fatal: execvp /usr/sbin/postdrop: Operation not permitted
sendmail    warning: command "/usr/sbin/postdrop -r" exited with status 1
sendmail    fatal: xcode@<redacted>.com(450): unable to execute /usr/sbin/postdrop -r: Undefined error: 0

Possibly a user issue? Anyone got any ideas?

@ddaddy
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ddaddy commented Feb 19, 2021

Yes. Unfortunately it seems on Big Sur it's not possible to amend the permissions chown: /usr/libexec/postfix: Operation not permitted as the root is now readonly.

@TonReurts
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TonReurts commented Nov 28, 2022

After this setup I get the following error:
-Queue ID- --Size-- ----Arrival Time---- -Sender/Recipient-------
0B3D68C4939 1669 Mon Nov 28 11:31:59 imac2019@iMac-di-iMac.fritz.box
(Temporary lookup error)
ton@reurts.com
What setting have I done wrong?

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