This study examined how four different configurations of unemployment and reemployment (defined by history of past unemployment and unemployment/reemployment 3years later) related to changes in psychological well-being. The longitudinal sample consisted of 566 Portuguese men and women who were unemployed at the beginning of the study. Using true change score models, we found that individuals who reported a long period of unemployment at T1 but were reemployed at T2 showed meaningful gains in positive affect and life satisfaction compared to those who had a shorter history of unemployment and were reemployed. An examination of gender differences revealed that the women who were reemployed after a long history of unemployment showed the greatest relative gains in positive affect. We conclude by noting limitations of this research and suggesting future research to address these limitations.