As schools across the country closed in March 2020 at the outset of the COVID-19 pandemic, it was not clear how long in-person education would be disrupted. The abrupt transition to remote learning was particularly challenging for districts in rural communities, many of which have long lacked reliable access to high-speed internet and technological resources for students. The unique circumstances of the pandemic required innovative solutions to address a deepening array of acute challenges faced by rural schools. In Colorado, the philanthropic community met the moment by supporting rural school systems in fundamentally new ways, upending traditional grantmaking processes to better address communities' needs through two key initiatives: the Planning and Design Support (PDS) initiative and the Education Innovation Fund. RESCHOOL Colorado's Learning Dollar initiative, a program connected to the Education Innovation Fund, also played a pivotal role by distributing money directly to families for education-related expenses. The deep collaboration among funders that occurred during these initiatives wasn't the only silver lining that emerged in the chaos and uncertainty of 2020. Schools and districts, especially those in rural areas, also set aside considerable time and resources, when both were scarce, to secure needed funding for their students and communities. In this paper, the authors describe the origins of these initiatives and their basic design before outlining a set of recommendations for how philanthropy in the state and elsewhere can build on these promising practices to improve future grantmaking. [WEND Collective and Lyra Colorado provided additional financial support for this report.]