The goal of this research was to observe which features, according to the users’ point of view, might influence the use of pillboxes. Older adults were surveyed in order to test different pillboxes and report their observations about their difficulties. Both the individuals and the pillboxes themselves have characteristics that might influence successful use, such as difficulty remembering medication names and lack of hand strength and the complexity of the pillboxes’ alarm system and opening mechanism. Pillboxes can be effective in helping older adults take their medication provided they are designed according to both dosage prescription and the user’s functional capacity.