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 [email protected]: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

Awesome. Thanks! One small thing. If postfix is not running, which it was not for me, then your shortcut
sudo postfix stop && sudo postfix start
fails to run the second half. So two lines would be suggested here.
sudo postfix stop
sudo postfix start

@crowmagnumb Your modification works for me and fixed my problem. Thx.

Seems like a great guide, but I'm having problems with the TSL configuration and have been trying to for hours now. Anyone getting;
TLS is required, but our TLS engine is unavailable
When using mailq after following above guide?

I'm also having the same problem with the TLS
(TLS is required, but our TLS engine is unavailable)
Anyone have a fix about it? Tks

@juwul I found how to fix here http://www.postfix.org/TLS_README.html#built-in

Enable tls:

sudo postfix tls enable-client

Reload:

sudo postfix reload

I run into postqueue: fatal: Queue report unavailable - mail system is down
after I run sudo postconf compatibility_level=2 and sudo postfix reload sudo postfix start

mailq is now working

If you are using gmail don't forget to enable "Less secure apps" - https://support.google.com/accounts/answer/6010255

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 [email protected]:password in sasl_passwd and can send emails and all my emails sender address is [email protected].

I want to replace [email protected] 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 [email protected]
(Temporary lookup error)
[email protected]
What setting have I done wrong?