In this chapter, we examine the dilemmas undergraduates experienced in helping predominantly Latino children complete homework assignments in the context of an after-school program. In doing so, we focus on important learning/teaching venues that involved undergraduates (the majority of whom have an interest in pursuing careers in teaching), the children and their families, and ourselves, the project leaders responsible for coordinating the after-school program and teaching classes that involved undergraduates as participants in the program. (PsycINFO Database Record (c) 2016 APA, all rights reserved)