The study explores the role of immigration policies in shaping immigrant labour market pathways, by looking at dynamic employment outcomes of migrants admitted through different entry channels (e.g. labour migrants, family dependants, students, refugees). It focuses on Italy, a country that in last decades, although the introduction of more structured immigration controls, has admitted a considerable number of undocumented immigrants (as well as migrants overstaying the entry visa), that have been subsequently legalised. In order to explore labour market outcomes of various categories of immigrants, data from the Italian survey Condizione e Integrazione Sociale degli Stranieri in Italia, that in 2011-2012 collected retrospective information on working and migratory histories of respondents, have been explored. Firstly, the transition to employment after the entrance into Italy is modelled using event history analysis, to observe if the transition rate changes by migratory status, given a set of socio-demographic and contextual characteristics. Secondly, the possibility of accessing a non-registered first job is developed though competing risks models, that account for multiple destinations. Finally, the current employment status is analysed through discrete choice models, comparing immigrants with different years since migration. Results show relevant differences by entry status in the likelihood of accessing employment and in the risk of entering a non-registered first job. For some categories of entrance (especially family and humanitarian migrants) the initial employment gap, although decreasing, persists over time, indicating a long-lasting condition of disadvantage.