Instructional tasks and assignments can often generate severe and high rates of problem behaviors for some students in special and general education. These daily instructional assignments or tasks often pose an aversive condition, thus favoring behaviors that effectively escape such a condition as functional. The author asks the rhetorical question: "Why are instructional tasks so aversive to some students?" To him, the answer to this question requires an analysis of the components of any given instructional task. Irrespective of the academic subject content, delivering instruction to learners involves two factors relevant to the individual learner (Cipani, 2017): (1) relative difficulty of the material (e.g., reading level required, prerequisite skills, fluency required); and (2) duration in which the learner is required to engage in the activity (i.e., instructional period or session length). This article focuses on how instructional difficulty affects problem behavior.