Using a sample of 848 workers in France, this article aims to explain problematic smartphone dependency, a behavior considered to have negative consequences for sufferers in the context of work. It examines whether and how addictive pleasure at work is related to problematic smartphone dependency (PSD). The authors propose a model with the originality of an exploratory measure of what is conceptualized as a mobile personal information system (PIS) development. The results obtained are paradoxical in that addictive pleasure at work is negatively correlated with PSD, although it positively contributes to the development of a PIS, the latter being itself positively correlated to gratifications. However, PIS development is not positively correlated to PSD. It is plausible that, although addictive pleasure at work drives the development of mobile PIS, it also provides an escape from compulsive smartphone usage, thus mitigating PSD. These findings also highlight the protecting role of mindfulness against PSD.