Initiatives that connect health care and housing services for people experiencing homelessness (PEH) have four key dimensions: aligning client preferences with practical options, maintaining ongoing interaction, reaching out where clients are, and co-locating services. A study based on interviews with staff from eight programs in New Jersey revealed insights into the challenges and strategies of these cross-sector collaborations. Motivations for collaboration included the significant effects of housing on health and the inefficiencies of addressing health needs without stable shelter. Successful approaches shared common elements, such as building rapport, intensive engagement, outreach, and service co-location. Effective policy recommendations included financing case management, clarifying licensing regulations, securing funding for nursing services in shelters, and enhancing support for frontline providers. While new federal policies may introduce challenges, they are unlikely to diminish the relevance of past experiences in effectively engaging PEH in health care and housing services. The findings offer valuable guidance for organizations aiming to implement similar cross-sector initiatives and improve the overall policy climate for these programs.