A growing body of research explores the influence of involuntary criminal justice contact on political participation, demonstrating that all types of contact weaken political participation. We posit, however, that personal connections to civil society organizations (CSOs) moderate the negative effects of involuntary criminal justice contact on political participation, particularly political activism beyond registering to vote and voting. We test this proposition with individual-level and aggregate-level data from metropolitan and municipal Chicago. Our findings confirm a paradox of participation by custodial citizens. One, we demonstrate positive, statistically significant, and substantive effects of personal connections to CSOs on nonvoting political participation by custodial citizens. Two, the negative effects of involuntary criminal justice contact on voting participation among individuals and communities may endure, despite personal connections to CSOs, even in a state where the franchise is restored immediately after incarceration. Our study suggests that an associational account of political participation deepens our understanding of the political behavior of custodial citizens and their communities in the age of mass incarceration.