The immediate months after prison are critical and can determine future trajectories of successful reintegration or recidivism. Finding employment after prison is considered a key condition to prevent recidivism; however, these individuals face numerous obstacles to finding work. Methodological difficulties prevent a thorough understanding of how these challenges impact job searching and working experiences of individuals after reentry. Using an innovative data collection method this dissertation contributes a detailed portrait of the job searching and working trajectories of 156 individuals. Participants were randomly sampled from a complete census of all recent releases to parole in Newark, New Jersey, and were followed for three months. Utilizing these data, the dissertation analyzes: a) the searching and working experiences of individuals at reentry, b) the use of social contacts for finding employment, and c) the association between emotional wellbeing and job searching. The manuscript also includes a methodological chapter, which describes the strengths and potential challenges of using smartphones as a data collection tool. Analyses of detailed smartphone measures reveal a reentry period characterized by very short-term, irregular, and poor-quality work. There is substantial heterogeneity across searching and working patterns, where older and less advantaged individuals sustained high levels of job searching throughout the study period. In contrast to prevailing notions, individuals are not social isolates or deeply distraught about their job searches; rather, they are highly connected to others and feel happier while searching for work. These results indicate that the low employment rates of reentering individuals are not due to person-specific deficiencies. Reentering individuals, however, remain deeply disadvantaged in the labor market, where they compete for work within a structure of reduced and limited opportunities. These findings challenge the established idea that finding suitable employment in today’s labor market is an attainable goal for reentering individuals.