First, I suggest replacing googlemail dot com with gmail dot com. Also, you must use Oauth authentication, not traditional password (although that still works on web access). Here are the basics: - change your security authorization to Oauth2 (do this for the server settings and also for the Outgoing (SMTP) server - two places - remove the password entries for the account (remove the entire entries both incoming and outgoing) - check to ensure that TB is set to accept cookies - Google will then step you through the authentication process for your PC.