The present study investigates the role of career adaptability in employee well-being within a period of two years. In addition, it aims to shed light on the boundary conditions that potentially determine the use of adaptability resources and thereby may moderate the relationship between career adaptability and work and life outcomes. The study was based on a representative sample of a Swiss working population from the French- and German-speaking parts of Switzerland. A total of 1,007 employed adults participated in the survey two years apart. Cross-lagged structural equation modeling analyses demonstrated a positive cross-lagged effect from career adaptability to job and life satisfaction. Conversely, a negative effect was observed with regard to perceived stress in life. In addition, our findings suggest that certain conditions (such as perceived limitation in career prospects and recent experience of significant work-related events) may strengthen some of the cross-lagged relationships between career adaptability and its positive outcomes. The present study contributes to the career construction literature in two ways. First, it tests a comprehensive cross-lagged model to inspect the longer-term effects of career adaptability on work-related and general well-being, thereby suggesting that career adaptability may have a role in longer-term adaptation due to its contribution to the maintenance of well-being levels. Second, we respond to a call for action regarding the boundary conditions under which career adaptability differentially predicts work and life outcomes (Rudolph, Lavigne, & Zacher, 2017). By identifying recent significant events and perceived career prospects as moderators, we begin to expose some of the complexities of career adaptability and career construction.