This chapter explores the need for a systemic and integrated approach to healthcare risk assessment. We firstly present epistemic issues related with the need of using data in context and on the intrinsic relationship between causality and risk in complex and evolving systems, like those that we find in the biomedical field and healthcare environments. We will then discuss how data processing encompasses multiple dimensions of decision-making and risk evaluations in order to ensure the safe and sustainable integration of digital technologies, particularly in healthcare. What follows is a multidimensional map to enhance risk evaluations and management strategies. We conclude exploring organisational, social, and ethical implications of adopting integrated and systemic approaches, showcasing their benefits/advantages, to effectively tackle the complexities inherent in digital healthcare, and we support the idea that integration and systemic approaches in risk evaluation and assessment help to enhance sustainable local solutions to global challenges in digital healthcare processes. Recognising the multifaceted nature of risks is fundamental, as risk is a contextual, often uncertain, undesirable harmful event or condition, associated with variability in future outcomes, and is closely tied to causality.