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moodle mail failed two ways in a swarm cluster. (1) moodle's build_context pulled the FULL sys-svc-mail-msmtp role early, which rendered /root/.msmtprc on the manager before Mailu had created the no-reply token and tripped the role's run-once flag, so the manager kept an empty-password msmtprc and the health check failed 'authentication method PLAIN needs a password'. Pull only tasks_from: ca_bundle so the manager re-renders on the normal post-token pass. (2) msmtprc forced host=127.0.0.1 for any in-container host, but the NFS server sits outside the swarm mesh and has no local Mailu, so it hit 'connect to 127.0.0.1:465 refused'. Narrow the 127.0.0.1 branch to compose or a real svc-swarm-node AND to when Mailu is actually deployed (email.external); else use email.host, and map the NFS node's test DNS to the manager IP. Also import the shared self-signed Root CA for the relay's TLS trust. Co-Authored-By: Claude Opus 4.8 (1M context) <noreply@anthropic.com>