Hello all, I spent a frustrating hour today hoping to setup git-send-email with my gmail account. I've been able to confirm the following: 1. git credential works # git config credential.helper osxkeychain # git credential fill <<EOF protocol=smtp host=smtp.gmail.com EOF outputs the correct username and password for my gmail account. 2. I (believe) I setup gitconfig properly: # git config --get-regexp sendemail sendemail.smtpserver smtp.gmail.com sendemail.smtpuser ben.knoble@xxxxxxxxx sendemail.smtpencryption tls sendemail.smtpserverport 587 sendemail.multiedit true sendemail.annotate true The strange behavior I'm seeing is that git-send-email - prompted me via macOS for keychain access (expected). This happened twice in a row, during one command invocation. - prompted me at the terminal for my gmail password (shudders) - stopped prompting me for messages send after that (all within the 15 minutes of the first two) Can anyone confirm/explain what's going on? I've never tried to use git-credential or git-send-email before, so I'm new to those (but experienced in git). D. Ben Knoble