O Positive Festival (O+) is a nonprofit organization that responds to the healthcare needs of artists and musicians. The Kingston festival—O+’s flagship event—is an annual weekend-long celebration in October, during which uninsured (i.e., without insurance) and under-insured (i.e., have insurance but at a cost that is too expensive to use) artists and musicians create and perform for the community in exchange for a variety of services donated by local healthcare providers. AmbitioUS is providing one-year grant for the ToO+lkit that will support O+’s overall efforts to help artists access healthcare through barter systems, which has become more urgently needed in light of the global pandemic.