Promoting a striving workforce in the face of digital job transformations remains a vital managerial challenge. Based on the conservation of resources theory, this work investigates how three job crafting strategies (cognitive, relational, and task crafting) can be constructive responses to technological content occupational insecurity, fostering job engagement and preventing exhaustion. In addition, instrumental leadership is examined as a moderator of these relationships. Hypotheses are tested with structural equation modeling and moderation analysis based on time-lagged survey data from 513 German employees. The results identify relational crafting and task crafting as coping responses to content occupational insecurity. Interestingly, instrumental leadership seems to be a boundary condition for the significant link between content occupational insecurity and cognitive job crafting. Furthermore, instrumental leadership moderates the link between content occupational insecurity and relational and task crafting, whereas the task crafting association seems to be dependent on other personal and environmental factors. These findings contribute to the literature on job insecurity and automatization and demonstrate the functioning of instrumental leadership as a facilitator of proactive job crafting in these contexts. We discuss the implications for theory and practice and avenues for further research.