Unlicensed patient care assistants (PCAs) are often tasked with providingconstant observation (CO)of patients withcomplex health behaviors. The unique demands of CO are poorly understood, making it challenging to design effective training.Four-componentinstructional design theory suggests the tasks associated with CO featurenon-recurrentchallenges, such that effective, simulation-based deliberate practice must reflect real-life variability.This study aimed toelucidate the variety of challenges PCAsencounter during CO of patientswithcomplex health behaviors. We used a qualitativedescriptivedesignand developed apreliminary framework to code interviews.The data collection framework wasdesigned to support creating numerous realistic scenariosto support generalized and transferable learning.From our interviews with 16 participants, we identified 1,066 statements associated with variations in CO tasks. We grouped our findings by two domains, "patient factors" and "environmental contexts." Our results revealed many recurring and non-recurring challengesinherent in CO, requiring arange of skills to maintain patient and staff safety.Instructional design elements may include scenarios incorporatingenvironment and resource assessment,cognitive feedback for non-recurrent tasks, novel methods of self-harm initiated by the patient, and incorporating interdisciplinary staff in which the learner must navigate a complex conversation. This studyclarifiesthetask demands of CO andisuseful as a task analysis to guide scenario development for simulation-based experiences. A less systematic approachwould risk underrepresenting the difficulties inherent in the task, reinforcing a limited set of behaviors that may not generalize well to the non-recurrent challenges in CO.