Proning, or turning a patient face down, is a technique used to manage patients with acute respiratory distress in intensive care units (ICUs). Research suggests that the type of pillow used in proning may have a significant impact on patient outcomes and increase the risk of disfiguring pressure injuries to the face. However, there is little evidence surrounding the usability of these pillows in the ICU. The aim of this study was to identify redesign opportunities by understanding how the tools, tasks, people, environment, and organization all interact during proning in the ICU. Thirty-six ICU clinicians from two Australian public metropolitan hospitals completed an online questionnaire regarding their opinions and experiences with proned patients and the prevention of pressure injuries. Seven ICU clinicians then completed journey mapping activities to document the key workflows, critical incidents, considerations, and personnel involved in managing proned patients in the ICU. Several barriers and facilitators to pressure injury prevention were identified, including interactions between the various tools (e.g., proning pillows with one opening limits the management of several medical devices), the tasks (e.g., high frequency of repositioning), the people (e.g., clinical inexperience, patient features), the environment (e.g., limited availability of tools), and the organization (e.g., limited number of staff to support tasks). This holistic approach revealed several opportunities for the redesign of proning pillows and associated systems. Key takeaways include the limitations of a one-size-fits-all approach to proning in the ICU context, and the need for flexibility and customization to improve proning pillows, associated medical devices, prophylactic dressings, aids, and processes.