Setup SENDMAIL on Mac OSX Yosemite

sendmail_setup.md

SENDMAIL on MAC OSX Yosemite

http://www.garron.me/en/mac/postfix-relay-gmail-mac-os-x-local-smtp.html

1. Create a file to store our credentials:

sudo vim /etc/postfix/sasl_passwd

2. Add something like this:

smtp.gmail.com:587 username@gmail.com:password

3. Now run:

sudo postmap /etc/postfix/sasl_passwd

4. Prepare the postfix main config file:

sudo vim /etc/postfix/main.cf

5. 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

6. Stop/Start the service

sudo postfix stop && sudo postfix start

7. Check the queue for any errors

mailq

Got below error message. Can someone help?
unknown: fatal: relayhost parameter setting must not contain multiple values: 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

@sunilbreddy, you need to put each parameter on a separate line. Just replace the space before each parameter with a line break, like so:

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

Thanks! It's working on my end but I have a little issue:

I've set: smtp.gmail.com:587 username@gmail.com:password in sasl_passwd and can send emails and all my emails sender address is username@gmail.com.

I want to replace username@gmail.com by user entered email. How can I get it?

Thanks in advance.

I am getting this error: postfix/postfix-script: fatal: the Postfix mail system is not running

I apologize for not responding to anyone. I've never received a notification until now.

@thedevxen I hope this helps. Check this out:
https://serverfault.com/questions/816113/postfix-postfix-script-fatal-the-postfix-mail-system-is-not-running

I apologize for not responding to anyone. I've never received a notification until now.

@thedevxen I hope this helps. Check this out:
https://serverfault.com/questions/816113/postfix-postfix-script-fatal-the-postfix-mail-system-is-not-running

Sorry, but I am not using "Server app" as asked in that question.

@thedevxen

Try this then restart the service. I hope this helps. If not, I'll try digging into later.

postconf compatibility_level=2

https://apple.stackexchange.com/questions/355986/configuring-and-running-postfix-mojave-10-14-4

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.

Works :-) thanks

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

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 have you tried this solution? Mail forwarding error in Plesk: unable to execute /usr/sbin/postdrop -r: Success 4.2.1 Message can not be delivered at this time

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.

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?