This article overviews the realities of so-called "low achieving" students in Singapore, efforts to support them better, and the place of educational technology in this support. We undertook a comparative case study of lower tracked Normal Technical (NT) secondary school students and their teachers in two schools in Singapore. We found a diversity of student backgrounds and struggles, with many students facing barriers to academic success and social mobility despite purported government efforts to support them. Findings also revealed a variety of approaches taken by their teachers, influenced by teacher ideologies of student backgrounds and abilities, pedagogy, and learning. Using the lens of selective digital technology integration, we highlight the promises and potentials of these efforts to improve NT student outcomes, along with the corresponding tensions and dilemmas. We conclude by arguing that a focus on innovation should mean pulling away from standard ideas of novel technological innovation and a move to collaborative, expansive, research-based pedagogy and systemic equity innovations.