The recent exemplification of multiliteracies in the newly implemented English Language (EL) syllabus in Singapore clearly signals to EL teachers the great importance of integrating technology-mediated communication practices into their classrooms. An initiative of the New London Group, multiliteracies is a pedagogical approach that points to the urgency and challenges of preparing students for a fast-paced, dynamic and multimodal world that now shapes all aspects of modern text consumption and production. Yet, EL writing instruction remains particularly resistant to such reforms. What we have instead is a persistence of long-dominant functional literacy strategies which emphasize technical skills, language rules, and learning by rote. This paper utilizes data gathered from a two-year, grant funded multiple-case study that investigated writing pedagogy on the part of six teachers working in three typical secondary schools in Singapore. It seeks to explain how functional literary persists to constrain the pedagogical actions of teachers, either explicitly or implicitly. It also identifies teaching opportunities that emerged in classroom observations but remained unexplored as a result of this functional literacy focus. Most importantly, the paper articulates how this historical trend may be challenged and overcome with a more robust multiliteracies pedagogy.