The study sought to investigate how successful schools in challenging contexts promote learner achievement despite the varied contextual odds. The book describes the structural settings of schools in challenging contexts. It further outlines the challenges that schools in such contexts encounter that militate against maximized learner achievement. It specifies the contextual challenges successful schools in such contexts face and uses a specially designed conceptual framework to help in exhaustive analysis and discussion of how such schools promote learner achievement. The study uses qualitative approach. It discusses findings in relation to relevant literature for an in-depth understanding of stakeholder involvement in mitigating contextual challenges to learner achievement in such contexts. The author suggests recommendations that would help such schools further promote learner achievement despite the contextual challenges. The findings reveal that in a challenging context, high learner achievement is realized when stakeholders acquire an understanding of their contextual difficulties and collectively craft structures that would best suit their contextual circumstances.