The current research examines the combined role of proactive personality and political skill in job crafting and work engagement by integrating the job demands-resources (JD-R) model and trait activation theory. Self-reported survey responses collected from three samples – university students (study 1, N = 363) and panel data (study 2, N = 300 and study 3, N = 206) – were analyzed using the PROCESS macro. Results revealed that political skill strengthened the relationship between proactive personality and work engagement and between proactive personality and job crafting when trait activated. Furthermore, perceived supervisor support did not interact with the job crafting–work engagement relationship with trait activation, suggesting that proactive individuals rely on self-resources to improve engagement when presented with trait-relevant situational cues. The findings extend JD-R theory to offer the interplay of proactive trait and political skill in facilitating overall job crating. JD-R is identified as a contextual condition for trait activation.