This paper examines why consumers join loyalty programs and what features keep them engaged. It also explores the relationship between the motivations to join loyalty programs and key features over time. Companies often differentiate their customer acquisition and retention strategies, but still find that “loyal” customers may not be truly loyal. Thus, it is important to segment customers based on their motivations for joining loyalty programs, and define proper retention strategies based on current customer perceptions and behaviors. Empirical data from Euromonitor’s International “Voice of the Consumer: Digital Survey” (2020–2024) worldwide sample was analyzed using descriptive stats, and multiple linear regressions explaining the specific features of participation in loyalty programs based on consumer motivations as independent variables. Most important findings show the main reasons for joining loyalty programs include discounts or offers, member benefits, and free products. Key features for continued participation are customer rewards, problem-solving assistance, convenient shopping processes, and expressing gratitude. All engagement and participation aspects over time are influenced by the motivation to receive discounts and offers. Problem-solving as a key feature in engagement over time is also influenced by access to exclusive rewards, better customer service, and free products. Convenience is positively influenced by exclusive rewards, better customer service, and discounts and offers, and negatively by exclusive experiences, member-only benefits, and free products. Finally, theoretical and managerial implications are discussed, suggesting value propositions should be tailored to individual motivations to boost participation and reduce churn. The paper also notes limitations and recommends future research directions.