Poor medication adherence is a widespread healthcare issue that directly impacts the effectiveness of the medication and the overall health of the patient. Wellth is a smartphone application offered to users challenged with managing chronic conditions to improve medication adherence through daily reminders and monthly financial incentives to help members form healthy habits. The study examined the effects of financial incentives on the medication adherence of members according to their characteristics including their age, gender, and location of residence in addition to the health conditions they were battling during a 5-month Wellth program. In this study, adherence was defined as the percent of days the users checked in all their medications within a ±3-hour task window while timely adherence was when check-ins were submitted in a narrower window of ±1-hour. Wellth demonstrated both positive and negative relationships between specific patients and adherence. By comparing the findings with the existing literature, patterns were evaluated, and hypotheses were made. The severity of the member’s illness and vulnerability to consequences seemed to go be joint factors. The complexities of medication regimens, side effects, and symptoms associated with their health condition affected patient motivation. Economic factors including financial status, healthcare access, and level of knowledge could also be used as an explanation. This study is important because it helps develop and implement effective adherence programs for different kinds of patients by examining what type of patients for whom incentives work best using a mobile app. Essentially, this helps target features and design new programs for those who did not respond well to financial incentives.