This paper reports on system trust and interpersonal trust issues revealed in an embedded-case study of two telemedicine services offered by a teaching hospital. Consistent with McKnight (2005) perceived system competence was an important dimension of system trustworthiness. Drawing on representation theory (Wand and Weber, 1995) we observed: 1. Some clinicians feel telemedicine provides a better representation than they can achieve in conventional practice. 2) The ability to control specific technical features leads to increased representational quality, perceived system trustworthiness and usage. 3) Some clinicians adapt the telemedicine system to improve it. 4) Some users do not distinguish between the technology artifact and a human helper when judging system trustworthiness. We conclude with two key findings: 1) judgments about system trustworthiness interact with users’ technical and clinical skills and 2) system trust and interpersonal trust are reciprocal.