Generation Z’s brand loyalties in the ride-hailing industry remain indefinable today. Despite their leading roles and long-standing experiences, Gojek and Grab are still concentrating of the refinement on their product design to capture the broad demands of the potential customers. This paper aims to examine how the ride hailing-apps are appraised by the Gen Z users while investigating how both producers capture and retain users’ loyalty at the same time. The study adopts a qualitative approach by interviewing nine Jakarta Gen Z users and five producers in the ride-hailing app industry using in-depth semi-structured interviews. The findings reveal four emerging themes related to the users’ appraised behaviors and expectations of the overall ride-hailing app and service experience. In the context of emotional design, this research empirically illustrates that clarity of information, simplicity of the app homepage, the relevance of content, and consistency in the design are the major aspects of a desirable established-app from the user’s perspective. However, these key elements do not guarantee users’ long-term commitment. They support the manifestation of positive emotions, experiences, and an attitude in which indicates loyalty meaning tolerance towards error.