I followed the step described in the link below to setup my mac to send out email. http://www.anujgakhar.com/2011/12/09/using-macosx-lion-command-line-mail-with-gmail-as-smtp/
It was working fine on my Mac OS X 10.9. But after I upgraded to OS X 10.10. The mail.log showed the following error. What is the problem?
Oct 19 00:28:22 paullam-macbook-pro.local postfix/smtp[30383]: 6B47B8AD4E8: SASL authentication failed; cannot authenticate to server smtp.gmail.com[74.125.68.109]: generic failure
Oct 19 00:28:24 paullam-macbook-pro.local postfix/smtp[30383]: 6B47B8AD4E8: to=<zzpaul@gmail.com>, relay=smtp.gmail.com[74.125.68.108]:587, delay=3.4, delays=0.01/0/3.4/0, dsn=4.7.0, status=deferred (SASL authentication failed; cannot authenticate to server smtp.gmail.com[74.125.68.108]: generic failure)
I had the same problem. A Google search turned up this link: http://hkitago.com/2014/09/yosemiteのpostfix設定/
It turned out I was missing the following line in /etc/postfix/main.cf:
smtp_sasl_mechanism_filter = plain
I added both snippets as suggested, but still no luck. Then I found this article:
http://www.developerfiles.com/how-to-send-smtp-mails-with-postfix-mac-os-x-10-8/
and ran the following steps from it:
Step 2. Create the sasl_passwd file We need to create the sasl_passwd file with the SMTP credentials
sudo vi /etc/postfix/sasl_passwd
Write the following content exactly (don't put in your user address and password) and save:
smtp.gmail.com:587 your_address@gmail.com:password
Create the Postfix lookup table from the sasl_passwd file.
sudo postmap /etc/postfix/sasl_passwd
This will create the file sasl_passwd.db
Step 3. Restart Postfix To apply all new changes we have to restart Postfix:
sudo postfix reload
And still no luck. But then I noticed that relayhost in /etc/postfix/main.cf
was commented out with brackets like so:
relayhost = [smtp.gmail.com]:587
I changed this line to:
relayhost = smtp.gmail.com:587
reloaded postfix with:
sudo postfix reload
and postfix started sending email. Hooray!
It turned out I needed another piece to get this to work.
sudo vi /System/Library/LaunchDaemons/org.postfix.master.plist
and right after this:
<dict>
add this:
<key>RunAtLoad</key>
<true/>
I can now send emails with Postfix on Yosemite!
Answer by @Josh is working just fine (can lot leave comments on the answer), but using login as a filter would also work just fine. Not sure what the difference is, though.
As stated by the documentation page
来源：https://stackoverflow.com/questions/26447316/mac-os-x-10-10-yosemite-postfix-sasl-authentication-failed