This chapter presents a case study of an English as a Second Language learner’s writing development over six years of schooling in the Maldives where English is the medium of instruction. Using writing samples collected from her schoolwork for English, and interviews regarding her writing process, this chapter explores how the learner’s writing developed over time and the possible individual, home and school factors that may have helped or hindered her writing skills. Findings suggest that her writing improved during the first few years, but then remained steady. The writing tasks assigned were restricted to a few text types, and there was little variation across the grades. The guidance received from school was limited and at times stalled the writing. For this participant, the home environment was a more significant source of encouragement and support. The role of adequate exposure to appropriate input in advancing writing proficiency, and the potential influence of implicit language policies on learner attitudes and identities are discussed.