In 2014, California implemented the Family Stabilization (FS) program within its Temporary Assistance for Needy Families (TANF) program, California Work Opportunity and Responsibility to Kids (CalWORKs). FS fills two key service gaps in TANF that have been identified in the literature—namely, addressing participant barriers to work and supporting child well-being. Research on programs addressing these gaps in TANF remains limited. This qualitative policy implementation study describes FS program design and implementation in 11 California county human service agencies and explores links to agency and community context. We find that state-encouraged flexibility resulted in three distinct approaches to FS services, staffing, and structure. Alignment between agency context and program design emerged as central to implementation decisions. These findings yield implications for research, policy, and management practice among welfare-to-work administrators.