This research examined whether the putative effect of incarceration on income poverty over the life course differs by marital status among a sample of male high school graduates. The purpose was to better understand the effects of imprisonment on a study population with relatively stronger economic prospects who have not been the focus of prior studies on the topic. Data were drawn from the 1975, 1992, and 2004 waves of the Wisconsin Longitudinal Study to yield an analytic sample of 2678 male high school graduates. We then estimated discrete-time hazard models to investigate (1) whether incarceration is associated with marital dissolution among married men, (2) whether incarceration is associated with marriage among unmarried men, and whether the effect of incarceration on income poverty differs by marital status among an aggregated sample of both married and unmarried men. Event history analysis revealed that men who experienced incarceration before age 25 were significantly more likely to fall into income poverty relative to men who were never incarcerated. However, men who experienced incarceration after marriage were also significantly more likely to separate or divorce, and unmarried men who experienced incarceration were significantly less likely to marry in the first place. The results imply that marriage as a path towards avoiding economic hardship in old age is seldom available to returning prisoners. Thus, the findings reinforce policy efforts aimed at education, job skills, and training as well as comprehensive family case management programs for formerly incarcerated individuals, couples, and families.