The PEO Digital C2ISR Division cost team has been utilizing JIRA to develop agile software development metrics for 4 years. This presentation will discuss how we have integrated ourselves with our software development teams, the complexity involved in extracting meaningful information from JIRA, and how we generate useful metrics and trend analyses for a number of different audiences. What are the right metrics to report to our software development teams at release planning events? We explore a number of metrics that assess the health of the team planning and development processes. What are the right metrics to report to our user organizations and operators? We explore a number of metrics that resonate with the user, such as capability and feature delivery rate and cycle times. What are the right metrics to support our senior leaders and decision makers? We explore metrics related to work allocation (requirements versus deficiencies, improvements and non-functional work), how it is changing over time, and effort levels (hours, dollars) required to sustain the capability and feature delivery rates. We will discuss a number of lessons that we have learned and insights we have gained during our 4 year journey of agile software development analysis and research in this large complex ISR portfolio.