ABSTRACT The introduction of self-service technology (SST), particularly self-checkout and self-scan services, has gained increasing attention from German retail. But to date, end-customer SST use has not developed extensively. The majority of German customers still prefer to use the traditional checkout service counter. The purpose of this paper is to explore how trust, fun, and usefulness can attract inexperienced prospective adopters and experienced customers to use SST. For this, our study investigated the intention to use an SST as a holistic system (self-scan and self-checkout) and considered trust in the SST technology for the first time. Also the interplay between fun and perceived usefulness has not been investigated before. The data were collected using an online questionnaire and in front of a German hypermarket that offers SST. The sample (n = 222) consists of both inexperienced and experienced customers. The data were analyzed using structural equation modeling in SmartPLS4. Results demonstrate fun is a decisive factor for a holistic SST system that incorporates the task of self-scanning and self-checkout. This also holds for trust and perceived usefulness. With regard to experienced and prospective users, the results show different effects in the importance of both groups. Fun is crucial for prospective users. For experienced users, benefits and trust become more important for long-term usage. Trust is an essential aspect for both user types. Managerial implications are discussed.