This study critically examines the multifaceted relationship between digital transformation, organizational resilience, and sustainability, emphasizing that their interaction is complex, contingent, and context-dependent rather than universally beneficial. Drawing on an integrative literature review, the chapter synthesizes theoretical and empirical insights from major academic databases, employing the Technology–Organization–Environment and Dynamic Capabilities Theory frameworks to explain how digital transformation shapes adaptive capacity and sustainable performance. The findings reveal a dual nature of digital transformation: It serves as an enabler of innovation, efficiency, and resilience, while simultaneously introducing challenges related to technological integration, cybersecurity, cultural change, and ethical dilemmas. Sectoral and contextual variations further mediate these outcomes, with SMEs, entrepreneurs, and technology-intensive industries experiencing divergent trajectories. The study develops a dual-pathway model illustrating both the enabling and inhibiting mechanisms of digital transformation and highlights leadership, culture, and institutional conditions as critical mediators. By bridging resilience and sustainability discourse, the research underscores the importance of human-centered, context-aware digital strategies that balance technological ambition with ethical, social, and environmental responsibility. Future research is encouraged to explore micro-foundations of digital resilience and longitudinal pathways of transformation across diverse organizational contexts.