The Integrated Logistics System - Supply (ILS-S) is one of the largest mission applications in the United States Air Force with 20,000 direct users and over 180,000 supported users world-wide operating 24x7 at over 280 global locations. ILS-S has undergone a transformation over the last two years by moving all development and production environments to the cloud while at the same time transitioning to a fully Agile delivery model with monthly deliveries of new capability. This presentation will look at the processes employed and lessons learned as the USAF moved the largest mission application to date with the largest operational data migration to date to the Cloud One environment using 18 development contractors and a highly collaborative agile program office. The end result was the migration of over 120 server instances with over 2TB of operational and 3TB of analytical data from an on-premises Defense Information System Agency (DISA) environment to Amazon Web Service (AWS) GovCloud environment. In the process the server footprint was reduced by 58 servers which is saving the USAF more than $444K/year. The migration required ILS-S to be off-line only one business day. The development environment, also in the cloud, has Continuous Integration/Continuous Deployment (CI/CD) and full DevSecOps with a streamlined Cloud One manual promotion process with a fully automated promotion strategy which allows for the migration of new capability from development to production in an hour.