Thanks for reaching out! A few comments about your setup:
It seems like your Automatic Deployment Trigger (ATD) will only trigger when:
A Machine is enabled.
A machine is found healthy after a health check.
A machines is found to be unhealthy after a health check.
If you want a deployment to trigger to all the machines in an environment as soon as a package arrives, you could do it like this:
A) [Recomended] Using only TFS steps. Instead of using Automatic Release Creation (ARC) and triggers, simply have 1 step in your TFS process that creates and deploys the release. If you are using TFS 2015 or 2017, you can use our plugin which will enable you a few new steps to achieve what I'm mentioning here: https://octopus.com/docs/guides/use-the-team-foundation-build-custo...
B) Set your lifecycle to automatically deploy to an environment when the releases reaches a phase. Instead of using Triggers, go to your lifecycle and add an environment to the first phase as "Deploy as soon as the release enters this phase" (See screenshot). When the release gets created, it reaches the first phase of the lifecycle by default, which will trigger the deployment.
tip: if you already have the environment on the first phase of the lifecycle, you will have to remove it and re-add it to see the options on the screenshot