Social service outreach workers serving homeless populations exemplify Michael Lipsky’s concept of street-level bureaucrats who exert considerable discretionary power in performance of their roles. In their efforts to qualify their homeless clients for housing, outreach workers create “fitting stories” that present their clients as qualified for support within the social service contexts that provide housing services. We describe outreach workers’ creation and negotiation of fitting stories with two audiences: homeless clients and institutional gatekeepers. Outreach workers respond to barriers to qualifying their clients for housing by creatively finding ways to manipulate clients’ biographical narratives and evidence to support those narratives in ways that “fit” their clients to agency criteria for housing services. In the process, outreach workers at times play loosely with the letter of the law in attempts to meet the spirit of the law in the service of their clients and agency expectations for service delivery.