Instruction abstracted from specific and concrete examples is frequently criticized for ignoring the context-dependent and perspectival nature of learning (e.g., Bruner, 1962, 1966; Greeno, 1997). Yet, in the effort to create personally interesting learning contexts, cognitive consequences have often been ignored. To examine what kinds of personalized contexts foster or hinder learning and transfer, three manipulations of perspective and context were employed to teach participants Signal Detection Theory (SDT). In all cases, application of SDT principles was negatively impacted by manipulations that encouraged participants to consider the perspective of the signal detector (the decision maker in SDT situations): by giving participants active detection experience (Experiment 1), biasing them to adopt a first-person rather than third-person perspective (Experiment 2), or framing the task in terms of a well-known celebrity (Experiment 3). These contexts run the risk of introducing goals and information that are specific to the detector's point of view, resulting in sub-optimal understanding of SDT. (Contains 3 figures and 8 tables.)