Private-sector contractualization is a problem as old as the Philippine Labor Code. Fully grappling with the breadth of its concept can be a monumental task that requires exploring new possibilities to engage with its many dimensions. Although it is pervasive and universally recognizable, policymakers, decisionmakers, practitioners, and the general public may easily find themselves lost in the thicket of its many specific nuances. By identifying a spectrum of licit to illicit arrangements that can be distinguished from regular employment, this article proposes a definition for contractualization to more clearly analyze its many components. This article presents an analysis of case law and historical legal developments focusing on the constitutional pillars of social justice, security of tenure, management prerogative, and self-organization to raise questions that reimagine the role that the Philippine Labor Constitution can play in addressing the issue of contractualization.