Configure Postfix for Gmail SMTP in Mac OSX

Configure Postfix for Gmail SMTP in Mac OSX.md

Configure Postfix for Gmail SMTP in Mac OSX

This should work on at least:

• 10.9 Mavericks
• 10.10 Yosemite

Taken from Using MacOSX Lion command line mail with Gmail as SMTP

Edit file /etc/postfix/main.cf and add this to the bottom:

# Configure Postfix for Gmail SMTP in Mac OSX Yosemite
# Added per https://gist.github.com/joech4n/72108461bfac1bf2e99f
# Set the relayhost to the Gmail Server.  Replace with your SMTP server as needed
relayhost = [smtp.gmail.com]:587
# Postfix 2.2 uses the generic(5) address mapping to replace local fantasy email
# addresses by valid Internet addresses. This mapping happens ONLY when mail
# leaves the machine; not when you send mail between users on the same machine.
smtp_generic_maps = hash:/etc/postfix/generic

# These settings (along with the relayhost setting above) will make
# postfix relay all outbound non-local email via Gmail using an
# authenticated TLS/SASL session.
smtp_tls_loglevel=1
smtp_tls_security_level=encrypt
smtp_sasl_auth_enable=yes
smtp_sasl_password_maps=hash:/etc/postfix/sasl/sasl_passwd
smtp_sasl_security_options = noanonymous

# To fix these errors per http://askubuntu.com/q/73865:
# Dec 15 17:14:12 localhost.local postfix/smtp[3691]: Untrusted TLS connection established to smtp.gmail.com[74.125.28.108]:587: TLSv1 with cipher RC4-SHA (128/128 bits)
smtp_tls_CApath = /usr/local/etc/openssl/certs
smtp_tls_CAfile = /usr/local/etc/openssl/cert.pem

# To fix these errors per http://stackoverflow.com/q/26447316:
# Dec 15 17:46:51 heimerdinger.local postfix/smtp[4758]: C9682156786: to=<[email protected]>, relay=smtp.gmail.com[74.125.28.108]:587, delay=1.3, delays=0.77/0.11/0.42/0, dsn=4.7.0, status=deferred (SASL authentication failed; cannot authenticate to server smtp.gmail.com[74.125.28.108]: generic failure)
smtp_sasl_mechanism_filter = plain

Create a sasl_passwd if one doesn't exist

sudo mkdir /etc/postfix/sasl
sudo vim /etc/postfix/sasl/sasl_passwd

and enter in the following:

[smtp.gmail.com]:587 [email protected]:password

Set up address mapping

Use the generic(5) address mapping to replace local fantasy email ([email protected]) addresses by valid Internet addresses ([email protected]). This mapping happens ONLY when mail leaves the machine; not when you send mail between users on the same machine. Set this up by editing /etc/postfix/generic.

sudo vi /etc/postfix/generic

and add the following (only think you need to replace is GMAIL_USERNAME:

[email protected] [email protected]
@host.domain     [email protected]

Protect credentials, create Postfix files, and restart Postfix

sudo chmod -R 600 /etc/postfix/sasl
sudo postmap /etc/postfix/sasl/sasl_passwd
sudo postmap /etc/postfix/generic
sudo launchctl stop org.postfix.master
sudo launchctl start org.postfix.master

Testing

echo 'test' | mail -s "contents" [email protected]

Errors?

If you receive the following error:

send-mail: fatal: chdir /Library/Server/Mail/Data/spool: No such file or directory

you can do the following:

sudo mkdir -p /Library/Server/Mail/Data/spool
sudo /usr/sbin/postfix set-permissions
sudo /usr/sbin/postfix start

as per this question.

NB: If things aint sending / receiving, and you're getting notices, check that the mail servers you're using are actually working!

and enter in the following:
[smtp.gmail.com]:587 [email protected]:password

Do you know whether it's possible to avoid store the password in plaintext? I would prefer to keep it encrypted, e.g., in the OSX keychain and extract it only on-demand via security find-generic-password.

This worked great, thank you!

Don't need the postmap if relaying through Gmail! Google will use your AUTH to automagically rewrite the sender.

From: Curtis Doty <[email protected]>
X-Google-Original-From: [email protected] (Curtis Doty)
Received: by shine.local (Postfix, from userid 501) id 989FA34850C8; Wed, 20 Sep 2017 17:58:09 -0700 (PDT)

And if the email comes from root, they are nice enough to change the username for you.

From: System Administrator <[email protected]>
X-Google-Original-From: [email protected] (System Administrator)
Received: by shine.local (Postfix, from userid 0) id D4AA534850CE; Wed, 20 Sep 2017 17:58:31 -0700 (PDT)

However... for extra-extra credit, if you do use a sender_canonical or other postmap to rewrite the sender, if it's an alias that Gmail has already verified, they honor that without any X-Google-Original-From header or mangling!

Hello, I am not getting my email sent out using the generic template from /etc/postfix/generic.
I am getting the error:
550-Verification failed for [email protected] 550-Unrouteable
address 550 unable to verify sender address (in reply to RCPT TO command)

I have included these lines inside /etc/postfix/generic:

[email protected] [email protected]
@imac.local [email protected]

Then I ran postmap generic and restarted postfix with this commands:

sudo launchctl stop local.org.postfix.master
sudo launchctl start local.org.postfix.master

Also did postfix reload.

But I still get the same 550 message.

Did anyone have such problem?

Thank you.

Here's what worked for me:

/etc/postfix/main.f

# Gmail SMTP relay
relayhost = [smtp.gmail.com]:587

# Enable SASL authentication in the Postfix SMTP client.
smtpd_sasl_auth_enable = yes
smtp_sasl_auth_enable = yes
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd
smtp_sasl_security_options =
smtp_sasl_mechanism_filter = AUTH LOGIN

# Enable Transport Layer Security (TLS), i.e. SSL.
smtp_use_tls = yes
smtp_tls_security_level = encrypt
tls_random_source = dev:/dev/urandom

/etc/postfix/sasl_passwd

[smtp.gmail.com]:587 [email protected]:PASSWORD

It's a great tutorial, and I've learned a lot from it

I got connection time out problem for sending email when I execute command mailq.

Here is the command output:

-Queue ID-  --Size-- ----Arrival Time---- -Sender/Recipient-------
8CF038D0FBDB     2915 Sat May 13 17:39:13  [email protected]
         (connect to smtp.gmail.com[108.177.125.109]:587: Operation timed out)
                                         [email protected]
                                         [email protected]

A912E8D0FC9C     3025 Sat May 13 17:41:41  [email protected]
         (connect to smtp.gmail.com[108.177.125.109]:587: Operation timed out)
                                         [email protected]
                                         [email protected]
                                         [email protected]

-- 5 Kbytes in 2 Requests.

I'm in China, maybe network can't access Gmail SMTP server. I'm not sure this is the reason.
Or is there a way to configure proxy for postfix?