The aim of this chapter is to determine what types of formal training methods can provide appropriate “mapping via training” of a new but related software application (in this case, a database management system [DBMS]), given that “mapping via analogy” is also taking place. To this end, trainees’ existing mental models were measured, and then the trainees were exposed to one of the three training methods. Training methods were varied in an experimental setting across two dimensions: the training task context (generic versus relevant), and the number of DBMSs demonstrated (one versus two). Outcomes were measured in terms of learning performance and perceptions of ability to transfer skills to a new but related DBMS. The results indicate that both task context and the number of software packages learned are important training variables that influence trainees’ mental models of the software, their transfer self-efficacy expectations, and their perceptions about the usefulness of the training.