Despite the robust correlation between math anxiety and math performance, little is known about how students’ perceptions of math task difficulty or employment of math strategies may relate to math task types. The purpose of this study was to examine differences in students’ task difficulty perceptions and math strategy use across types of math tasks (i.e., overtly or covertly timed, simple or complex problems). Participants included 113 fourth- and fifth-grade students who completed four study conditions in a randomized, counterbalanced order in which tasks varied in terms of timing (i.e., covert or overt) and task difficulty (simple or complex computation). Students demonstrated small to medium differences in task difficulty perceptions and strategy use across their baseline trait math anxiety and math performance such that students with higher trait math anxiety reported using more strategies and tasks being more difficult. Generally, math task timing did not affect perceived difficulty or strategy use. Implications for research and practice are discussed. Impact Statement Student perceptions of math tasks and the strategies they employ can affect their math performance and engagement with math, which in turn can impact future math performance. Of note in this study, fourth- and fifth-grade students with math difficulties and high initial math anxiety demonstrated better math performance and lower perceived task difficulty under overtly timed conditions, underscoring the utility of timing for math fluency performance, particularly for students with math difficulties.