This chapter provides a constructive exploration of future trajectories in digital business transformation across Africa, introducing a novel Contextual Digital Transformation Framework (CDTF) tailored to decipher this intricate phenomenon. Through an in-depth qualitative analysis, utilizing expert interviews and secondary data, the chapter highlights key drivers actively shaping Africa's digital landscape. These include mobile-first innovation, emerging technologies such as 5G, IoT, and AI, the fintech revolution, and the evolving regulatory challenges present in the region. The CDTF is structured around four significant pillars: Contextual Embeddedness, Adaptive Innovation, Network Dynamics, and Multi-level Agency. This framework serves as a valuable tool for analyzing digital transformation, particularly in resource-constrained contexts. The chapter applies the CDTF to delve into future trajectories, uncovering how contextual factors and adaptive strategies together foster digital innovation across diverse sectors. The insights gained contribute meaningfully to theoretical discussions surrounding technology adoption in emerging markets while also providing actionable insights for businesses, policymakers, and development practitioners. By shedding light on Africa's unique journey of digital transformation, this chapter not only aids in shaping strategy and policy within the continent but also enhances the global comprehension of digital innovation in various contexts.