In this paper, the author examined the results of one classroom assignment submitted by preservice teachers to explore different representations of a division-by-fraction expression. Given one expression, the preservice teachers were asked to evaluate the expression, write a word problem modeling this expression, and describe an activity using manipulatives to illustrate the expression. The preservice teachers, the majority of whom are elementary generalists, were also asked to describe their math confidence in understanding the concept of division by a fraction.