Migrating Five Teams from Jira Cloud to Data Center

A Department of Defense program under the Office of Military Community and Family Policy needed to move five application teams from Jira Cloud to an on-premises Data Center environment with an Oracle backend.

The migration

I led the migration for five application teams, including the systems administration and information assurance groups. The work included configuring the Data Center instance, setting up plugins (Structure, Advanced Roadmaps, Checklists), migrating user data, and transitioning 100 users to a certificate-based central login system. Each user needed profile setup, certificate attachment, email sync, and training.

Rebuilding the configurations

Beyond the technical migration, I rebuilt the Jira configurations to match how the teams actually worked. Custom JQL filters, workflows, screen schemes, and permission schemes were tailored to each team's process. I built a Zero Trust security roadmap in Jira alongside the information assurance team, defining milestones and integrating project timelines.

Automation

I halved administrative overhead for product owners by implementing automation rules for the MilitaryOneSource WordPress, .NET, and mobile application teams. Automated tasks included initiating test cycles, moving stories through workflows, generating sprint reports in Structure, and updating Confluence pages. The teams spent less time managing their tools and more time doing their work.