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Rules: When-Then, Flows and Groovy
44

Since @Rich update it works fine with Gmail guys, just configure it like this
update first:
docker-compose -p openremote pull
then docker-compose.yml

environment:
      OR_SETUP_TYPE:
      OR_ADMIN_PASSWORD:
      OR_SETUP_RUN_ON_RESTART:
      OR_EMAIL_HOST: ${OR_EMAIL_HOST:-smtp.gmail.com}
      OR_EMAIL_USER: ${OR_EMAIL_USER:-my@email.com}
      OR_EMAIL_PASSWORD: ${OR_EMAIL_PASSWORD:-myappspecificpassword}
      #OR_EMAIL_PROTOCOL: smtps
      #OR_EMAIL_PORT: 465
      #OR_EMAIL_TLS: "false"

You only need to configure host, user, app-specific password