This article uses interviews with dependent immigrant women and men in Canada to analyze immigrant disadvantage in the labor market and workplace. Synthesizing feminist social policy scholarship with sociological studies of gender, work, and migration, we develop a framework for analyzing how migration, care, and employment regimes intersect to generate disadvantages. We find that gendered disadvantages embedded in dependent migration policies accumulate through a family-market care regime and a racialized, precarious employment regime. Both women and men dependent immigrants are disadvantaged in the labor market and workplace through multiple, accumulating dynamics; yet we also find different degrees and pathways to disadvantage, and multiple strategies to navigate it, shaped by gender and class. We argue that analyzing both the structure of inequalities produced by intersecting regimes and the ways people navigate them over time is key to understanding the contradictory mechanisms that both produce disadvantage and provide openings for strategic maneuvering.