For irregular migrants, status regularization can open the door to transformative opportunities including legal residency, secure employment, access to social services, and family reunification. Expanding access to legal status–whether through speedy asylum procedures, sponsorship programs, amnesties, or other paths–is often a key goal animating the work of migration researchers, activists, and policymakers. Yet is status regularization always unambiguously positive? How do states use regularization to pursue coercive and restrictive aims? And how do irregular migrants resist such efforts and with what consequences? Building on two years of ethnographic fieldwork and in-depth interviews with young Syrian men living in Lebanon, this paper answers these questions by exploring the contours and consequences of a Lebanese government campaign to regularize the status of Syrian laborers and small business owners who possessed neither a UNHCR registration certificate nor up-to-date residency paperwork. In late 2018, Lebanese General Security began enforcing dormant regulations to regularize Syrian-owned small businesses and target Lebanese enterprises that employed Syrians without the requisite sponsorship (kafala). The fines, fees, and paperwork associated with regularization often exceeded the average annual earnings of a Syrian worker or business owner. This article follows three key interlocutors caught up in this campaign: 1) a wage laborer who resisted incorporation into the kafala system, 2) a small business owner who risked everything by evading regularization, and 3) a restauranteur who pursued legal sponsorship. Through these ethnographic cases, I show how regularization unraveled the fragile web of income-generating activities that supported the small Syrian middle class, producing unprecedented levels of precarity and raising significant doubts about Lebanon’s viability as a place of a refuge. For my interlocutors, this pressure forced difficult choices about whether to evade, resist, submit, flee, or return to Syria at a moment when inflation had begun to erode the value of their savings upon which the viability of their plans and mobility was based. In these circumstances, I show how the move to incorporate migrant workers and entrepreneurs into a formal legal status regime was, paradoxically, also an efficacious way to push them out without violating the principle of non-refoulment, as movement under the duress of regulatory strangulation was illegible to humanitarian agencies that narrowly conceptualized involuntary movement as the product of physical violence.