Despite the widespread interest in using and researching simulation in higher education, little discussion has yet to address a key pedagogical concern: difficulty. A "sociomaterial" view of learning, explained in this paper, goes beyond cognitive considerations to highlight dimensions of material, situational, representational and relational difficulty confronted by students in experiential learning activities such as simulation. In this paper we explore these dimensions of difficulty through three contrasting scenarios of simulation education. The scenarios are drawn from studies conducted in three international contexts: Australia, Sweden and the UK, which illustrate diverse approaches to simulation and associated differences in the forms of difficulty being produced. For educators using simulation, the key implications are the importance of noting and understanding (1) the effects on students of interaction among multiple forms of difficulty; (2) the emergent and unpredictable nature of difficulty; and (3) the need to teach students strategies for managing emergent difficulty.