Project Tomorrow's® annual Speak Up Research Project has documented the evolution of technology use, both from an instructional and operational perspective, within K-12 education since 2003. Since 2017, the Speak Up results have also included a focus on K-12 districts' cybersecurity preparations. However, today, the combination of the expansion of technology resources within the K-12 education enterprise and the increase in cyber threats to school districts has mandated that a more comprehensive review of the state of cybersecurity within K-12 education be conducted. In partnership with iboss, a new Speak Up Research effort was initiated in spring 2021 to understand the views and values held by school district leaders on their overall readiness to address these unprecedented cybersecurity challenges. Nearly 600 district administrators and technology leaders from a representative cross section of school districts nationwide responded to the call for input on this urgent topic by completing an online survey between January and May 2021. This report identifies and discusses three specific K-12 Cybersecurity Insights from the Speak Up research that can provide district leaders with a starting point for developing a new cross organizational approach for their district's cybersecurity preparation. [This report was co-prepared by iboss.]