Setting up your Gmail account to work with your Macs mail application means that you can get all your mail delivered straight to your desktop without needing to go online for it. This video also walks you through some of the basic settings you might want to use for your mail accounts so that you can. Apple Mail is the default email client that comes with every Mac using OS X 10.0 or later. Additional steps for older versions of Apple Mail that were released prior to Sierra have been included. It's normal for this to happen due to Media Temple's servers not having autodiscover settings enabled.

A quick howto setup Mac OS X and Postfix to use Gmail as a relay. Everything will need to be executed as root using sudo. If you just need to send emails try running sudo postfix start, and make sure to check your spam for emails – they will likely be flagged as they originate from a local mail server. SASL Authentication Connecting to the Gmail SMTP server requires both SSL and authentication. To set up authentication you will need to edit the /etc/postfix/sasl_passwd file. Sudu vi /etc/postfix/sasl_passwd Update the contents to include the following.

Note that enclosing hostnames with square brackets – [] – tells Postfix to avoid doing an MX lookup. Make sure to replace EMAIL with your email address, and PASSWORD with your Gmail password, properly escaping any colons in it. [smtp.gmail.com]:587:PASSWORD Use the postmap command to update the SASL credentials in Postfix. Sudo postmap /etc/postfix/sasl_passwd Postfix Relay Configuration Next we need to edit the Postfix configuration found in /etc/postfix/main.cf.

Sudo vi /etc/postfix/main.cf I was not able to route mail to the Gmail SMTP servers over IPv6, so force only IPv4 connections by searching for the inet_protocols key and updating the value. Inet_protocols = ipv4 If any of the following keys already exist in your configuration comment them out, and include the following at the bottom of the config file. # 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. Smtp_use_tls = yes smtp_tls_security_level = encrypt tls_random_source = dev:/dev/urandom Restart Postfix & Test Restart Postfix as root, then send a test email. Sudo postfix stop && sudo postfix start date mail -s 'Test Email' If you don’t receive the test email, check the Postfix queue by running mailq or looking at the contents of /var/log/mail.log.

Any errors that mention “ SASL authentication failed” indicate that you may have entered an incorrect email/password combination, forgot to run postmap after updating the credentials, or need to Turn On in Gmail for your account. If you’ve configured 2-Factor authentication with Google, you’ll need to create an app password to bypass the 2FA. See this article for assistance. Quickbooks 2016 for mac disk.

When entering the password on the sasl_passwd file, you’ll need to supply the app password instead of your personal password. If you have already entered your personal password and are now entering the app password, dont forget to run the “sudo postmap /etc/postfix/sasl_passwd” prior to restarting postfix. Also, postfix on OSX Sierra is version 3.1.X which may have issues leading to log entries stating it can’t find the md5 algorithm. Upgrading to OSX High Sierra also does an upgrade to postfix 3.2.X which solves the issue. My first guess would be that the username or password is incorrect – just to double check the auth info goes into /etc/postfix/ sasl_passwd (you have sass_passwd in your comments as well as the correct spelling). If the file is named correctly you might need to escape your password if it has any special characters (dollar sign, asterisk, etc) as they might not be interpreted correctly.

Also check out the link in the error you are getting – there are a few troubleshooting steps on that page regarding two factor authentication, allowing “less secure” apps, or possibly unlocking your account.

I had resolved all the gmail vs. Mail issues in El Capitan, but after upgrading to Sierra the problems are back. When I compose and send a message from Mail, I end up with a draft in gmail attached to the thread of messages which is unsent, despite having sent it in Mail. The message is sent, but it remains as a draft in gmail.

If I delete those, I am deleting my copy of the sent message in gmail,but if I send them from within gmail I will be sending the same email twice. Anyone else seeing related issues with Mail and gmail not getting along again?