This study examines how healthcare professionals and administrators experience and respond to volatility, uncertainty, complexity, and ambiguity (VUCA) during digital transformation, integrating SWOT analysis to capture systemic strengths, weaknesses, opportunities, and threats. Thirty-five semi-structured interviews with physicians, nurses, and administrators (2021–2024) were analyzed abductively within the combined VUCA-SWOT framework. Volatility reflected technological acceleration; uncertainty arose in decision-making and telemedicine; complexity involved fragmented infrastructures and workforce shortages; ambiguity appeared in inconsistent training, intergenerational digital divides, and reduced human connection. The VUCA-SWOT lens provides strategic insights to enhance resilience and guide sustainable healthcare delivery in evolving environments.