The advent of digital finance and online money management (OMM) services has changed the ways in which we conduct everyday transactions. Based on my preliminary F32 survey findings, the number of older adults who use technology is drastically growing and the way they approach financial transactions is certainly changing. Given the increasing number of older adults and corresponding diseases of aging such as Alzheimer’s Disease (AD), the vulnerability of older adults to financial exploitation, and the pervasiveness of financial decision making in everyday life, it is critical to be able to accurately examine financial decision making using objective, quantifiable, and ecologically valid tasks that are in keeping with the current trends. In 2016, an expert panel working for the US Social Security Administration found a gap between the current assessment of financial decision making and real-world financial performance. The current proposal seeks to bridge this gap by developing and applying simulation technology-based OMM task to assess financial decision making in individuals across the spectrum of cognitive aging. Accordingly, the first two aims (K99/Mentored phase) of the current proposal are to establish the reliability and validity of a novel, simulated OMM credit card statement review task in cognitively healthy older adults via psychometrically rigorous approaches. The third and fourth inferential aims (R00 phase) are to use: (i) a longitudinal strategy to track OMM over time and in relation to cognitive changes in cognitively healthy older adults, and (ii) a cross-sectional strategy to examine OMM in two clinical groups (mild AD and those judged as financially incapable by Adult Protective Services) versus healthy older adults. To accomplish these aims, I will develop advanced skills to supplement my strong neuropsychological training, by: 1) gaining expertise in developing and conducting functional assessments using state-of-the-art technology; 2) developing a deeper knowledge of psychometric measurement to optimize task design; and 3) enriching my conceptual understanding of financial decision making while learning how to incorporate neuroeconomic principles and metacognitive assessment in financial decision making measurement. I have assembled an excellent and well-rounded mentorship team consisting of a computer scientist, biostatistician, gerontologist, economist, and expert neuropsychologists. Overall, this K99/R00 proposal enables me to lay a foundation for an independent research career focused on using technology to accurately conceptualize financial decision making in cognitively diverse older adults, a goal that is in line with the NIA’s mission to improve “the health, well-being, and independence of adults as they age”.