[T]he State of New York, and particularly New York City, pushes its poor, disabled sex-offender registrants into homelessness, and then prolongs registrants’ detention because of their homeless status. This detention regime continues unabated, despite studies showing that sex-offender recidivism rates are actually relatively low and that residency restrictions do not demonstrably prevent sex offenses. Rather, such laws consign registrants to homelessness, joblessness, and social isolation. It does not have to be this way. This Essay suggests litigation strategies to challenge the prolonged detention of homeless registrants on statutory and constitutional grounds. The Essay also offers policy solutions to improve New York City registrants’ access to housing and to untether an individual’s housing status from their access to liberty. New York simply cannot and should not continue both to restrict registrants’ housing options and to detain individuals because they are homeless.