In this essay, the authors describe the results of a scholarship of teaching and learning project that conducted a qualitative study of the writing development of 21 student writers during the first year of college, tracking their progress in an English 101 course and following them as they moved into the core, transfer-level composition course. The authors use the writing of three students as case studies to illustrate the challenges that beginning college writers face as they transition from introductory to degree-requirement composition courses and attempt to meet the demands of increasingly complex reading and writing tasks. Their classroom research reveals that students who straddle the basic/developmental writing and college-level writing borderland struggle to translate instruction into rhetorical adaptability. When faced with challenging new reading and writing tasks in the core, transfer-level composition course, students in this study reverted to rhetorical strategies typical of pre-English 101 instruction. Their findings emphasize the importance of cultivating students' metacognition as part of the writing curriculum, highlight the benefits of process pedagogy at all stages of precollege and first-year college composition, and argue for text-based writing assignments in introductory writing courses. (Contains 4 notes.)