I approach the philosophical analyses of the phenomenon of trust vis-à-vis online communication beginning with an overview from within the framework of computer-mediated communication (CMC) of concerns and paradigmatic failures of trust in the history of online communication. I turn to the more directly philosophical analyses of trust online by first offering an introductory taxonomy of diverse accounts of trust that have emerged over the past decade or so. In the face of important objections to the possibility of establishing and (...) fostering trust in online environments—objections that emerge especially from the perspective of virtue ethics and phenomenological approaches to how we know and navigate the world as _embodied_ beings—I then take up three major arguments in recent work in favor of the possibilities of trust online, followed by three _vicious circles_ that run counter to more optimistic views. I close with a summary of some additional reasons for optimism regarding trust online, followed by a final question that emerges out of recent CMC research on social networking sites that poses, I argue, fundamental challenges indeed to how we understand and may foster and experience trust online. (shrink)