The present study aimed to investigate the relationship between parental leave length and maternal depressive symptoms at six- and twelve-months postpartum and whether this relation was influenced by women’s attitudes towards leave, whether leave was paid or unpaid, and the reason they returned to work. The sample included 115 working women recruited during pregnancy as part of a larger longitudinal study. Analyses revealed that maternal attitudes toward leave influenced the association between leave length and depressive symptoms. Specifically, longer leaves were associated with increased depressive symptoms for women who missed their previous activities at work. Furthermore, women who missed work and had leave for 16 weeks or more, exhibited higher depressive symptoms at six- and twelve-months. Last, results also indicated that women who returned to work solely for monetary reasons exhibited more depressive symptoms at six-months postpartum than those who returned to work for other reasons. This study is among the first to show that women’s attitudes towards parental leave and their individual reasons for returning to work are important factors to consider that may have potential implications for parental leave policies.