Here is the log.
Email The Autobiography of Benjamin Franklin to
BroCraig@free.Kindle.com
connect: (u'smtp.gmail.com', 587)
connect: (587, u'smtp.gmail.com')
reply: '220 mx.google.com ESMTP i10sm4101034anh.12\r\n'
reply: retcode (220); Msg: mx.google.com ESMTP i10sm4101034anh.12
connect: mx.google.com ESMTP i10sm4101034anh.12
send: 'ehlo rev-craig-beemans-macbook-pro.local\r\n'
reply: '250-mx.google.com at your service, [72.156.148.50]\r\n'
reply: '250-SIZE 35651584\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-STARTTLS\r\n'
reply: '250 ENHANCEDSTATUSCODES\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [72.156.148.50]
SIZE 35651584
8BITMIME
STARTTLS
ENHANCEDSTATUSCODES
send: 'STARTTLS\r\n'
reply: '220 2.0.0 Ready to start TLS\r\n'
reply: retcode (220); Msg: 2.0.0 Ready to start TLS
send: 'ehlo rev-craig-beemans-macbook-pro.local\r\n'
reply: '250-mx.google.com at your service, [72.156.148.50]\r\n'
reply: '250-SIZE 35651584\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-AUTH LOGIN PLAIN XOAUTH\r\n'
reply: '250 ENHANCEDSTATUSCODES\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [72.156.148.50]
SIZE 35651584
8BITMIME
AUTH LOGIN PLAIN XOAUTH
ENHANCEDSTATUSCODES
send: AUTH <censored>
reply: '235 2.7.0 Accepted\r\n'
reply: retcode (235); Msg: 2.7.0 Accepted
send: u'mail FROM:<BroCraig@gmail.com> size=502619\r\n'
reply: '250 2.1.0 OK i10sm4101034anh.12\r\n'
reply: retcode (250); Msg: 2.1.0 OK i10sm4101034anh.12
send: u'rcpt TO:<BroCraig@free.Kindle.com>\r\n'
reply: '250 2.1.5 OK i10sm4101034anh.12\r\n'
reply: retcode (250); Msg: 2.1.5 OK i10sm4101034anh.12
send: 'data\r\n'
reply: '354 Go ahead i10sm4101034anh.12\r\n'
reply: retcode (354); Msg: Go ahead i10sm4101034anh.12
data: (354, 'Go ahead i10sm4101034anh.12')
send: 'Content-Type: multipart/mixed; boundary="===============8196497422022582706=="\r\ nMIME-Version: 1.0...
reply: '250 2.0.0 OK 1299775902 i10sm4101034anh.12\r\n'
reply: retcode (250); Msg: 2.0.0 OK 1299775902 i10sm4101034anh.12
data: (250, '2.0.0 OK 1299775902 i10sm4101034anh.12')
send: 'quit\r\n'
reply: '221 2.0.0 closing connection i10sm4101034anh.12\r\n'
reply: retcode (221); Msg: 2.0.0 closing connection i10sm4101034anh.12