This study analyzes factors associated with transitions into and out of disconnectedness, which is defined as being disconnected from the labor market, welfare, and other substantial financial supports. Findings are based on discrete-time hazard models estimated with a sample of New Jersey welfare recipients followed for 5 years. Work history, human capital, policy environment, and economic conditions are found to be the factors most strongly associated with the dynamics of disconnectedness. More work history and human capital are associated with a lower probability of becoming disconnected and a higher probability of leaving disconnected status for employment. Individuals relying on unemployment insurance benefits are at high risk of becoming disconnected. This suggests that the expiration of such benefits often leads to disconnectedness. Receipt of sanctions for noncompliance with welfare’s work requirements are found to triple the risk of becoming disconnected. Finally, transitions into disconnectedness increase sharply with increases in the unemployment rate.