Learning to counsel patients in a teaching clinic or hospital occurs in the presence of the competing agendas of patient care and student education. We wondered about the challenges that these tensions create for clinical novices learning to deliver bad news to patients. In this preliminary study, we audio-taped and transcribed the interviews of seven senior optometry students and six optometrist instructors at a Canadian optometry teaching clinic. The participants described their experiences in learning to deliver bad news. Using a grounded theory approach, our analysis was informed by situated learning and activity theory. Optometry students received formal classroom training regarding how to deliver bad news, including exposure to the medically-based six-step SPIKES protocol (Baile et al. "The Oncologist, 5," 302-311, 2000). Yet, application of this protocol to the teaching clinic was limited by the lack of exposure most instructors had received to this strategy. Determinants of the students' complex learning process during their clinical apprenticeship, included: (i) knowing one's place, (ii) knowing one's audience, (iii) knowing through feedback, and (iv) knowing who speaks. The experiences of these participants pointed toward the need for: (1) more instructional "scaffolding" (Bruner and Sherwood "Play: Its role in development and evolution," p. 280, 1976) in the clinical setting when the learning task is complex, and (2) explicit discussions about the impacts that unfold when the activities of patient care and student education overlap. We reflect on the possible consequences to student education and patient care in the absence of these changes.