Hi Monks,

I just wanted to write up what happened with smtp.google.com on the 30th of May. Auth 2.0 came into effect, which deprecated use of a username and a password, requiring instead an app key. An effective work-around is described in Re^3: sending an email from my rpi to my droplet [gmail workaround].

I found the error message instructive:

$ echo "BEEP BEEP" | mailx -s "Subject: This is a test!" tallharry84@g
+mail.com
send-mail: authentication failed (method PLAIN)
send-mail: server message: 534-5.7.9 Application-specific password req
+uired. Learn more at
send-mail: server message: 534 5.7.9  https://support.google.com/mail/
+?p=InvalidSecondFactor s8-20020a62e708000000b0051835ccc008sm2037121pf
+h.115 - gsmtp
send-mail: could not send mail (account default from /home/pi/.msmtprc
+)
send-mail: cannot log to /var/log/msmtp.log: cannot open: Permission d
+enied
send-mail: log info was: host=smtp.gmail.com tls=on auth=on user=tallh
+arry84 from=tallharry84@gmail.com recipients=tallharry84@gmail.com sm
+tpstatus=534 smtpmsg='534-5.7.9 Application-specific password require
+d. Learn more at\n534 5.7.9  https://support.google.com/mail/?p=Inval
+idSecondFactor s8-20020a62e708000000b0051835ccc008sm2037121pfh.115 - 
+gsmtp' errormsg='authentication failed (method PLAIN)' exitcode=EX_NO
+PERM
Can't send mail: sendmail process failed with error code 77
$
[download]

Typing in the 16-letter app output in the place of the password does the trick.

I went ahead and opened up the site they mention and found it worth a read: Signing in with App Passwords. The world is a-changin' as far as authentication goes. Passwords are no longer for sticky notes on the wall. 2-factor auth is necessary, and if you don't have a phone number to give google, they're not gonna let you play.