While cloud adoption in government has accelerated in recent years — especially during the pandemic — the processes and tools needed to support this modernization have not kept pace. And even though governments have become more versed in procuring cloud technologies, there is a need for CIOs and procurement officials to develop enterprise roadmaps for modernization to ensure long-term success. Drawing from results from a survey of 128 government leaders conducted in April 2021 by the Center for Digital Government (CDG) and expert interviews, this paper outlines the key challenges governments face and offers strategies to plan, procure and secure cloud solutions in ways that serve rapidly evolving constituent needs.