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Digital health technologies are advancing rapidly and are beginning to reshape how care is accessed, delivered, and financed, creating new possibilities for more timely, patient-centered, and resilient health systems. At the same time, their large-scale adoption is constrained by persistent barriers such as unequal access and digital literacy, unresolved questions around data privacy, security and ownership, limited interoperability between fragmented systems, cultural resistance within organizations, and uncertain reimbursement and sustainability models. This chapter offers a concise map of this landscape by outlining key challenges, including the digital divide, governance of health data, integration and interoperability, change management, “pilotitis,” and ethical risks, as well as major opportunities, from AI-enabled decision support and personalized medicine to real-time analytics, value-based care, and gamified approaches to engagement. It also highlights how these issues intersect across regulatory frameworks, implementation strategies, equity considerations, and emerging innovation paradigms discussed in later chapters. It argues that the same technologies that can deepen fragmentation and inequity, if poorly governed, can also be harnessed through deliberate policy, design, and business models to generate durable, system-wide benefits.