Part of a larger research project, subordinated to the comprehension of the experience of homelessness in contemporaneity, this paper focuses on the analysis of the roles that vocational training and transitions to and from the labor market, assume in the context of experiencing this form of severe deprivation. Although quite unknown to professionals, agents with governance responsibilities (local, regional and national), as well as citizens, homelessness comprises, for many of the adults inhabiting the Portuguese territory, (un)successful training experiences and fragile and inconsistent professional integration. We are, today, faced with a high volume and heterogeneity of homelessness emergency, maintenance and exits paths, in which are included various experiences of training (e.g., short or long term, vocational or academic nature), as well as attempts, temporally varied, of integration into the labor market. In the absence of a cohesive and coordinated strategy to combat homelessness, these individuals are confronted with extreme difficulties not only in training or employment modalities integration, but also in its successful concretization, given the major difficulties (e.g., financial, housing) daily faced. To understand the above questions the researcher mobilized the contributions of Classical Grounded Theory methodology, from which a theoretical model explaining the different processes that embody varied paths that homelessness conforms, and, in this range, the roles that the multiple experiences of training and employment possess in its experimentation. Entitled surviving the streets, the GT generated emerged from the analysis of information gathered through complementary observation methods (unstructured observation, observation during street outreach, that included 434 night street interventions), and consultation of diverse documentation and 96 interviews [homeless (n = 38), professionals (n = 47), previous homeless people (n = 11)]. In this original conceptual proposal are exposed, according to a parsimonious, coherent and empirically supported organization, the discursive and behavioral patterns predominantly mobilized for the purpose of resolving the problems/difficulties homeless face. Stands out, from the set of narratives, the substantial shortage of professional offers that comply with the legislation currently applied, factor that is associated to severe constriction of vocational training modalities in which they are, in fact, integrated. It is also relevant that for most respondents the possibilities of engaging in productive activities are often limited to the parallel economy and, in the extreme, to the experience of victimization in the context of undertaking slave work for organized trafficking networks. The last part of the paper signals the indispensability of modifying the legislation and intervention frames, in Portugal and the EU, on this matter.