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This paper takes a case-based approach to describe the dynamic processes inherent in digital transformation (DX). Using a theoretical modeling approach, Fujikawa, Kondo, and Imai (2022) proposed a dynamic process model in the form of a two-dimensional matrix with two axes (platform and stakeholder), four quadrants (stages) and two transitions (paths). Based on a theoretical sampling approach, the current study identifies four cases (Askul, Pioneer, Komatsu, and Nihon Kotsu) as “DX cases that went through different stages and paths” and analyzes these examples as revelatory and longitudinal cases. The paper explores the possibility of integrating new insights and logic detected in the case analyses back into the conceptual model.