The global push for digital transformation in education has reached Sierra Leone’s secondary schools, promising enhanced classroom management through technology. Yet beneath the policy rhetoric and donor-funded tablet distributions lies a complex reality that this study sought to understand. Using the Technology Acceptance Model (TAM) as its theoretical lens, this qualitative case study investigated digital classroom management practices across ten secondary schools in Sierra Leone, five urban and five rural. Through semi-structured interviews with 30 teachers and 10 principals, focus group discussions with students, classroom observations, and document analysis, the research uncovered a landscape marked by stark contradictions. Findings revealed that while digital tools have created unprecedented opportunities for student engagement through multimedia instruction and improved administrative efficiency through digital attendance tracking, these benefits remain deeply uneven. Infrastructure deficits, erratic electricity, and patchy connectivity continue to undermine even the most committed digital initiatives. More significantly, the study found that teachers’ digital literacy levels and their perceptions of technology’s usefulness (a core TAM construct) varied dramatically based on access to training and peer support. The research contributes empirically grounded insights to the limited scholarship on digital classroom management in post-conflict, resource-constrained contexts. Policy implications point toward the need for integration-focused strategies that address pedagogical support alongside infrastructure provision, suggesting that Sierra Leone’s educational technology investments must prioritize teacher capacity building and context-appropriate solutions over hardware-centric approaches.