An increasing number of students are entering colleges underprepared and, because of their high numbers, are shaping the core of academic culture (Adler-Kassner, 2000). In response to this growing enrollment, conversations among basic writing teachers and scholars have centered mainly on the issue of curriculum content. Yet how do we best instruct basic writing students who often appear inattentive, ambivalent and isolated? A recent grounded theory research study of 13 teachers of basic writing students suggests that discussion centered on the question, "How do we teach?" may augment the teaching and learning paradigm in the increasingly complex basic writing classroom. Interviews with practitioners reveal that enhancing teacher-student interactions in order to achieve higher learning outcomes is a complicated endeavor-one that requires teachers to: 1) become aware of student needs, most especially the need to develop confidence (Shaughnessy, 2003), as well as to: 2) understand the unique dynamics of this student population. Basic writing students often struggle with personal problems and insufficient academic and social skills; in addition, they generally hold a complex attitude toward learning. This presentation provides an overview of the multifaceted basic writing student population and discusses the complications that arise in developing stronger teacher-student interactions.