A major health and societal challenge nowadays is how to ameliorate and/or delay the onset of cognitive decline in humans suffering from diverse pathologies. Often, solutions can be found in basic science conducted in the laboratory through the use of very well-known experimental procedures. In the present review article, we set out to present the main findings from a research line that uses an experimental procedure originally discovered in animal studies investigating associative learning, the differential outcomes procedure (hereafter the DOP). Here we review the main findings of the DOP that relate to the different processes involved in associative learning and memory from a neurophysiological perspective. We take a step forward to illustrate how the DOP can be applied to real life settings to address important issues such as treatment adherence. Briefly, we first show how the DOP can be adapted to enhance discriminative learning and memory retention in children of different ages, younger adults, and healthy as well as pathological aging. Next, we illustrate how the DOP can be a cost-effective approach to tackle health challenges such as adherence to medical prescriptions in older people suffering from multiple morbidities. Finally, we discuss digital, mobile-based applications using the DOP to promote autonomy in older adults. Future directions in the DOP applications to health issues are also presented.