In this study, methodology and theory were linked to explicate the nature of education practice within schools facing exceptionally challenging circumstances (SFECC) in Trinidad and Tobago. The research design was an iterative quan>QUAL-quan>qual multi-method research programme, consisting of 3 independent projects linked together by overall purpose. Although large-scale quantitative data were first used to identify and describe SFECC, the overall programme was driven by an inductive theoretical thrust, with findings from the multiple-site case studies of Projects 2 and 3 used to construct substantive theory on SFECC. The integrated findings point to the pervasive role of beyond-school factors, which were magnified and intertwined with between- and within-school factors. SFECC in this study found great difficulty transcending states of chronic low performance. We hypothesized on the need for transformative school leadership, but in this context, greater external support by stakeholder agencies and broad place-based strategies appeared essential for turnaround.