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=<[email protected]>, 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