The chapter examines patterns of in-work poverty in contemporaneous Chilean society. The study presents in-depth information on institutional context and quantitative analysis from the National Socioeconomic Characterization Survey (CASEN) for the period 1990–2013. Cross-national comparisons indicate a significant incidence of working poverty in Chile. The authors associate this pattern with characteristics of the Chilean institutional contexts, mainly significant labor informality, strong labor market regulations and a welfare system based on mean-testing and a conservative male-breadwinner model. Micro-analysis with household survey data for 2013 provides evidence in favor of these associations. Furthermore, longitudinal analysis of the period 1990–2013 indicates that strong welfare retrenchments during the 1990s are associated with increases in in-work poverty, but only when relative measures are used. Results based on absolute poverty indicate a negative trend with stagnation in recent years. On the basis of the findings, the authors suggest implications for policy and research.