machine imap.gmail.com login username@gmail.com password ApplicationSpecificPassword port imaps
machine smtp.gmail.com login username@gmail.com password ApplicationSpecificPassword port 465  ; have tried 587

export EMAIL="username@gmail.com"
export NAME="My Name"
export SMTPSERVER="smtp.gmail.com"

(setq
 send-mail-function 'smtpmail-send-it
 message-send-mail-function 'smtpmail-send-it
 user-mail-address "trevorgrahambell@gmail.com"
 smtpmail-starttls-credentials '(("smtp.gmail.com" 465 nil nil)) ; tried 587
 smtpmail-auth-credentials (expand-file-name "~/.authinfo")
 smtpmail-default-smtp-server "smtp.gmail.com"
 smtpmail-smtp-server "smtp.gmail.com"
 smtpmail-smtp-service 465 ; tried 587
 smtpmail-debug-info t ; where is this output?
 starttls-extra-arguments nil
 starttls-gnutls-program "/usr/bin/gnutls-cli" ; executable, correct path
 starttls-extra-arguments nil
 starttls-use-gnutls t
 smtpmail-local-domain "my.dotted.ip.address"
)