The article presents a review and analysis of cybersecurity policy and strategic initiatives by the Obama Administration, and an argument for continuity and improvement of initiatives already in motion through the Trump Administration that will allow for growth of critical cybersecurity strategies that will improve critical infrastructure protection, modernize and defend the U.S. federal IT enterprise, and secure U.S. and allied investments in cyberspace. A discussion on key strategic efforts of the Obama Administration from 2008 to 2016 is presented, as well as challenges and potential improvements that could be made in the Trump Administration. We conclude by making several recommendations for U.S. policymakers that would provide continuity and iterative improvement to President Obama’s cybersecurity policy strategy: deepen the federal cybersecurity bench, accept recent bipartisan recommendations for policy improvement and strategic direction, and continue U.S. leadership in public-private and international partnerships.