The purpose of the study was to describe participants’ experience of daily weighing and to explore factors influencing adherence to daily weighing among individuals who were successful in losing weight during a behavioral weight loss intervention. Participants completed a 12-month weight loss intervention study that included daily self-weighing using a Wi-Fi scale. Individuals were eligible to participate regardless of their frequency of self-weighing. The sample (N = 30) was predominantly female (83.3%) and White (83.3%) with a mean age of 52.9 ± 8.0 years and mean body mass index of 33.8 ± 4.7 kg/m2. Five main themes emerged: reasons for daily weighing (e.g., feel motivated, being in control), reasons for not weighing daily (e.g., interruption of routine), factors that facilitated weighing, recommendations for others about daily weighing, and suggestions for future weight loss programs. Our results identified several positive aspects to daily self-weighing, which can be used to promote adherence to this important weight loss strategy.