This chapter surfaces examples of the ways educators, programs, and families are making connections to and from out-of-school time (OST) experiences and into other contexts in learners' lives, including additional programs, homes, communities, and schools. Through a review, the authors test, refine, and expand a design framework for connections across settings described in connected learning scholarship and identify shared goals and outcome indicators for collectively fostering equity through connective OST practices. The review has implications for practice in terms of offering design principles, examples, and outcome indicators for making connections that policymakers, program leaders, and educators can take up and for research by investigating and theorizing the role connective practices in OST programs can play in learning ecosystems.