Safely Upgrade Your Pipelines from Azure DevOps Server 2019 to Server 2020

This post details a critical upgrade path for Azure DevOps Server 2019 to 2020, specifically addressing the significant changes in the build retention model. It explains the limitations of the 2019 model (pipeline-level settings, difficulty inferring retention reasons) and the improvements in the 2020 model (project-level settings, retention leases for explicit reasons). The post provides a step-by-step guide to safely upgrade by disabling the new retention model on Server 2019, backing up the database, upgrading to Server 2020, creating leases for important pipeline runs, re-enabling the new retention model, and removing pipeline-specific retention policies. It also includes an FAQ addressing retention behavior when the new model is off and the fate of manually retained runs.