Facilitating research in the cloud presents a unique set of challenges for Research Computing and Data facilitators, researchers, students, and institutions. In this panel we focus on the challenges and obstacles faced by facilitators and some of the tools, methods, and approaches used at various institutions to overcome them and lessons learned. Areas of discussion will include cloud training for facilitators and researchers, what workloads are appropriate (and not) for the cloud, the importance of adapting and fundamentally changing workloads for the cloud, managing the plethora of services and vendor lock in, cost management, and some of the valuable lessons learned and fundamental changes in thinking along the journey to the cloud. This panel will take the perspective of utilizing the most popular public cloud providers but will be relevant to most cloud-native environments (including on-prem cloud).