I'm trying to setup alpine (formerly PINE) on OSX and GMAIL keeps bouncing my login attempts by saying alpine is not a secure client / to use the web client instead.
I'm not using 2FA (so no app passwords) - so has anyone gotten alpine & gmail to cooperate recently?
Currently (August 2018) google generates app-specific passwords for your smtp client needs. (edit: I missed OP reference to two-factor authorization, so this answer while awesome is a little off topic). My experience configuring alpine 2.21 installed through home-brew was pretty painless.
Visit your google account settings and generate a password. In alpine use that password with a viable configuration, for example at the main menu type S, C (setup, configure), smtp-server: smtp.gmail.com:587/tls/user=example@gmail.com.
When you send a message you'll use the app-specific password instead of your general account password. Google instructions tell you not to write it down, but in alpine you'll use it for sending and receiving separately.
Also: Alpine may work to save passwords insecurely on your local machine if you touch ~/.alpine-passfile and then persist through confirmations, failures and repetition. From research I understand that you can compile alpine with keychain support but I haven't gone down that route.
