This vignette chapter aims to reflect on the importance of teaching context in the assessment of ESL and EFL writing. The chapter will identify how factors like location, student population, and objectives can affect the strategies and methods used to assess student writing. Three main contexts will be explored: a first-year composition class at a major four-year university in the United States, a community ESL program in the United States, and a high-stakes EFL program at a private university in Mexico. The author will use her experiences as a teacher in these contexts to discuss how each presents unique challenges.