Background/Objectives: Academic engagement plays a central role in students’ learning outcomes and persistence in higher education. However, the mechanisms through which amotivation influences engagement remain insufficiently understood, particularly within conditional self-regulation frameworks. The present study examined a conditional self-regulation model in which amotivation predicts academic engagement through forethought and self-reflection under different levels of perceived performance control. Methods: Data were collected from 530 university students from Western Romania. A moderated parallel mediation model (PROCESS Model 59) was estimated to test whether forethought and self-reflection mediate the relationship between amotivation and academic engagement and whether perceived performance control moderates these pathways. Results: The results indicated that amotivation maintained a robust direct association with academic engagement across levels of performance control. Perceived performance control moderated the amotivation–forethought pathway, while self-reflection showed conditional indirect effects depending on control levels. Conclusions: These findings suggest that motivational deficits operate within a context-sensitive regulatory architecture in which control beliefs shape the activation of self-regulatory processes. The results contribute to understanding academic adaptation under motivational constraints and highlight the role of perceived performance control in students’ self-regulation systems.