The Chicago Transit Authority (CTA) has invested significant time and money into developing homeless outreach programs. Thresholds and Haymarket Center offer services on the trains themselves while The Night Ministry sets up outreach hubs at two stations. Drawing on interviews with staff from these outreach organizations, a researcher, a CTA bus driver, and several people who have sheltered on transit, this paper examines the dynamics between the CTA, outreach workers, and homeless riders, and analyzes how the CTA can best support a population with diverse backgrounds, needs, and desires. Ultimately, the CTA needs to address the inconsistency of its employees’ treatment of homeless riders and shift its focus even further from getting people off the trains towards prioritizing helping the homeless on their system. The CTA must also continue to invest in the existing outreach programming. Public transit cannot be separated from the homelessness crisis, and these essential outreach programs help it to have a positive impact on the homeless.