JFrog successfully migrated its cloud services from Helm v2 to Helm v3 to improve security and efficiency, as Helm v3 eliminates the need for the Tiller server and offers new features and greater stability. The migration process involved using the helm-2to3 plugin and could be done manually for a few releases or automated for larger numbers using shell scripts, which was necessary for JFrog's enterprise-scale operations running thousands of Kubernetes clusters across AWS, Azure, and Google Cloud. While the migration was mostly straightforward, challenges included ensuring Helm v3 labels and annotations were added to migrated Kubernetes objects, particularly for older releases that failed to upgrade automatically. The transition highlights the importance of staying up-to-date with software versions to maintain security and functionality across cloud services.