Abstract: Undergraduate students engage in substantial mathematical activity beyond the classroom, yet the instructional relationships surrounding these experiences remain underexplored. In this presentation, I trace a series of interconnected investigations examining students' engagement with homework and undergraduate peer tutors' experiences. Building upon earlier research, I discuss how investigations of peer tutoring motivated an extension of the Instructional Triangle to incorporate tutors as a fourth instructional agent. I then examine tutors' reported experiences and actions with written and online homework and how instructors' expectations contribute to refining this theoretical framework. Finally, I introduce a proposed investigation of student-tutor interactions and consider its potential contributions to understanding undergraduate mathematics learning beyond the classroom.