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Handlers run in definition order, and "Generate CA trust override" was defined before "Build compose". On a first deploy the override read the Entrypoint and Cmd of every service image with docker image inspect before compose build had created the locally built tags, found none, and left those services without the with-ca-trust wrapper; on later deploys it read the previous build's Entrypoint and Cmd instead of the new one. The override and the compose config validation now run after the build and rebuild handlers and before compose up; pull stays first. The swarm handlers already build before they generate their override and use no wrapper, so they are unchanged. TestFirstDeployFlush replays the shell handlers of one compose-build plus compose-up flush in the order handlers/compose.yml defines them and asserts that compose up starts the freshly built image behind the wrapper. Local deploy: all six stacks with a built image carry the wrapper in compose.ca.override.yml, nextcloud for 8 of 8 services. Co-Authored-By: Claude Opus 5.5 (1M context) <noreply@anthropic.com>