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The deploy CLI shipped every mode as -e KEY=value, which ansible-playbook parses as a string at the highest precedence. MODE_DEBUG=false therefore arrived as the non-empty, and so truthy, string false. Every when: MODE_X | bool was unaffected because the filter maps it back, but four sites read a flag bare and silently inverted: openldap wrote LDAP attributes with state exact on every deploy instead of only under MODE_CLEANUP, SYS_SERVICE_DEFAULT_STATE was restarted where it should have been omit, SYS_SERVICE_RUNNER_STATE was never started, and mailu always logged at DEBUG. Send the modes as one JSON extra-var, which keeps the declared type, and give those four sites the | bool they were missing so the meaning of a flag no longer depends on how its value reached Ansible. A lint pins the rule: a MODE_* read in a truthiness position carries the filter or a nocheck naming a genuine string comparison. Co-Authored-By: Claude Opus 5 (1M context) <noreply@anthropic.com>