Tor is a popular privacy tool designed to help achieve online anonymity by anonymising web traffic. Employing cognitive walkthrough as the primary method, this paper evaluates four competing methods of deploying Tor clients, and a number of software tools designed to be used in conjunction with Tor: Vidalia, Privoxy, Torbutton, and FoxyProxy. It also considers the standalone anonymous browser TorPark. Our results show that none of the deployment options are fully satisfactory from a usability perspective, but we offer suggestions on how to incorporate the best aspects of each tool. As a framework for our usability evaluation, we also provide a set of guidelines for Tor usability compiled and adapted from existing work on usable security and human-computer interaction.