Core self-evaluations (CSE) have predictive value for important work outcomes such as job satisfaction and job performance. However, little is known about the mechanisms that may explain these relationships. The purpose of the present study is to contribute to CSE theory by proposing and subsequently providing a first test of theoretically relevant mediating paths through which CSE may be related to work engagement. Based on approach/avoidance motivation and Job Demands-Resources theory, we examined a perception (via job characteristics), action (via job crafting), and development path (via career competencies). Two independent samples were obtained from employees working in Germany and The Netherlands (N = 303 and N = 404, respectively). When taking all mediators into account, results showed that the perception path represented by autonomy and social support played a minor role in the relationship between CSE and work engagement. Specifically, autonomy did not function as a mediator in both samples while social support played a marginally significant role in the CSE-work engagement relationship in sample 1 and received full support in sample 2. The action path exemplified by job crafting mediated the relationship between CSE and work engagement in both samples. Finally, the development path operationalized with career competencies mediated the relationship between CSE and work engagement in sample 1. The study presents evidence for an action and development path over and above the often tested perception path to explain how CSE is related to work engagement. This is one of the first studies to propose and show that CSE not only influences perceptions but also triggers employee actions and developmental strategies that relate to work engagement.