In Trinidad and Tobago, elementary school students transition to secondary schools after writing the Secondary Entrance Examination (SEA), which determines which school they are placed at. Up to 2013, that examination comprised summative assessment in Mathematics, English Language Arts, and Composition. During the period 2013 to 2016, however, a continuous assessment component (CAC) was introduced, requiring amongst other things, that students produce a portfolio of written pieces. Teachers were mandated to use the process approach to writing and attended training provided by the Ministry of Education. The purpose of this descriptive case study (Merriam & Tisdell, 2016) was to explore how teachers operationalized process writing, and what factors influenced their instructional decisions. The participants comprised two teachers each from two schools, who were observed during writing instruction sessions and subsequently interviewed. Findings point to superficial use of key aspects of the process writing approach; teachers’ apparent misunderstanding of the concept of writing workshop; as well as conceptual and school situational factors that account for teachers’ instructional decisions.