In response to recent cybersecurity incidents such as SolarWinds, Microsoft Exchange, and the Colonial Pipeline ransomware attack, President Biden on May 12, 2021 signed an Executive Order (EO) to improve the nation’s cybersecurity and protect federal government networks. For close observers, this seems to be like Groundhog Day, as past incoming administrations have issued similar executive orders to address insufficient cybersecurity defenses that leave public and private sector entities vulnerable to attacks. The National Institute of Standards and Technology (NIST) Cybersecurity Framework and the Department of Homeland Security’s Continuous Diagnostic and Mitigation (CDM) Program are good examples of past attempts to strengthen the federal government’s security posture and improve cyber resilience. The big question is whether the proposed actions in this new EO are attainable.