In response to the COVID-19 crisis, school districts worked quickly to roll out distance learning plans in the spring. Sometimes these plans impinged upon or were directly in conflict with provisions found in collective bargaining agreements (CBAs) negotiated between teachers' unions and district administration. In this brief, we unpack how urban school systems changed CBAs to make way for learning under COVID-19 conditions. We review COVID-19–related contract changes in 101 urban school districts around the country. We find that twenty-five urban school districts returned to the bargaining table with teachers’ unions to negotiate short-term fixes to CBAs that allowed for more flexibility to implement distance learning. These contract changes focused on several areas of the CBA, including compensation, workload, non-teaching duties, evaluation, leave, and technology. We argue that the lessons learned in spring contract negotiations have implications for the design and implementation of fall schooling plans, and that how fall schooling plays out will shape teacher morale and labor relations beyond the 2020–21 school year.