As wireless technologies evolve, mobile technologies and services will increasingly affect our lives, accompanied by positive and negative effects. This development requires a high acceptance of users to the presence of mobile services in various usage contexts. In an exploratory focus-group-interview approach (n = 63), this research investigates usage motives as well as barriers, which are perceived by users of wireless mobile technologies. In order to understand the impact of specific usage contexts, in which mobile services are applied, an ICT context was contrasted to a medical service context. Outcomes show that acceptance factors are neither static nor independent from the specific usage or service context in which a technology is applied. Rather, acceptance reveals to be a product of individual usage motivations, situation-specific evaluations, and individual user profiles.