Using a multistate sample of marriages that took place in the 1990s, this study examined associations between premarital cohabitation history and marital quality in first (N = 437) and second marriages (N = 200) and marital instability in first marriages (intact N = 521, divorced N = 124). For first marriages, cohabiting with the spouse without first being engaged or married was associated with more negative interaction, higher self-reported divorce proneness, and a greater probability of divorce compared to cohabiting after engagement or marriage (with patterns in the same direction for marital positivity). In contrast, there was a general risk associated with premarital cohabitation for second marriages on self-reported indices of marital quality, with or without engagement when cohabitation began.