When COVID-19 hit, Holyoke School District was nine months into an ambitious three-year strategy, the Homegrown Talent Initiative (HTI), designed to help rural communities across Colorado better prepare youth for success after high school by offering new career exploration and training opportunities. In the midst of school closings, remote learning, and community hardship, Holyoke found time to finalize its plan. This brief explores how Holyoke and other HTI districts increased youth access to internship and dual enrollment opportunities in the 2020-21 school year, while the pandemic disrupted opportunities like these for students nationwide. We found: (1) Community creation of a new definition of student success deepened districts' commitment to redesigning the high school experience, which propelled them to move forward with ambitious implementation plans; (2) Support from the technical assistance providers helped rural districts cultivate the capacity they needed to maintain progress; and (3) Early efforts to transform district policy and monitor quality moved communities in the direction of sustained, systemic change. [Additional funding for this research was provided by the Gill Foundation and Adolph Coors Foundation.]