Through case studies of adult literacy learners and the volunteer tutors who instructed them, this article illustrates the strengths and challenges faced by these kinds of instructional pairs. The descriptions help to reveal critical issues that can inform researchers' and practitioners' thinking and practice with regard to tutor training and ongoing support of instructional pairs. These issues are meant to serve as a starting point for rethinking commonly accepted tutor training practices. Findings indicate the importance of providing tutors with ongoing, situated assistance based on the particular needs of tutors and their students.