OBJECTIVE: The night out task (NOT) was developed as a naturalistic, open-ended, multitasking measure that requires individuals to complete eight subtasks comparable to those encountered during real-world functioning (e.g., pack travel bag, prepare tea). We examined psychometric properties and administration feasibility of this direct observation measure within a clinic-like setting using a tablet-based coding application. METHOD: A sample of 148 community-dwelling older adults (82% cognitively healthy; 18% mild cognitive impairment) and 57 younger adults completed the NOT along with other neurocognitive tests and questionnaires. RESULTS: Inter-rater reliability across NOT primary (i.e., time, accuracy, efficiency) and process-related (e.g., error-types, self-corrections) variables was mostly excellent. NOT primary measures showed expected patterns of convergent and discriminant validity with measures of cognition, demographics, and well-being. External validity was established by the NOT ability to distinguish between age and diagnostic (cognitively healthy vs. mild cognitive impairment) groups. Demonstrating incremental validity, the NOT primary variables (execution time in particular) were predictive of self-reported functional abilities and completion quality of in-home everyday tasks over and earlier variables such as demographics, cognition, and mobility. CONCLUSIONS: These findings suggest that the NOT and its app interface, which allows for continuous logging of observations, are a feasible in-clinic measure to assess cognitive capacities important for real-world functioning. With further validation, the NOT may allow for earlier detection of functional difficulties. Understanding errors and strategies used during NOT performance could also have implications for individualized interventions.