When children transition from Head Start to kindergarten, they may face different environments and expectations, which can cause disequilibrium and challenges for young children who benefit from routines. These kindergarten transitions occur within a broader context of distinctly different systems, with differing and sometimes contradictory governance structures, policies, philosophies, and accountability metrics. The HS2K case study was designed to help us learn more about how Head Start programs and Local Education Agencies (LEAs) can better support children and families through that transition. This brief provides strategies from the HS2K project’s collective work and real-life examples of how Head Start programs and LEAs work together to support kindergarten transitions. (author abstract)