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The Schedule

The Schedule is Headmaster’s automated task system. You define recurring or one-time tasks, and the agent runs them on a cron schedule — daily check-ins, weekly reports, periodic data pulls, recurring reminders. A scheduled task fires a predefined prompt against a chosen agent and specialist on a schedule.

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Two execution modes

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Creating a scheduled task

1

Open The Schedule

Click The Schedule in the left sidebar.
2

Create a task

Click Create task and fill in the form.
3

Save

Click Save. The task appears in the active tasks list with its next run time.

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Task form fields

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Schedule types

For most schedules you don’t need to write cron — pick a frequency preset and Headmaster generates the expression for you.

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Cron expression reference

Headmaster uses standard 5-field cron (no seconds field):

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Common expressions

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Special characters

  • * — any value
  • , — list (e.g., 1,3,5)
  • - — range (e.g., MON-FRI)
  • / — step (e.g., */15)
The cron expression field is in Headmaster’s Library (PIN-gated). In My Headmaster, schedules are shown as plain language (“Every weekday at 9am”) — you never have to read or write cron unless you want to.

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Keep-awake

By default, the agent stops running when you close the app. With Keep-awake enabled on a scheduled task, the runtime keeps running in the background even if the desktop window is closed. The task fires on schedule and delivers the result to your configured channel. The Schedule list page also has a global Keep-awake toggle that prevents your system from sleeping while Headmaster is open — useful for overnight runs.

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Catch up

If you miss a scheduled trigger (your machine was off, or the runtime was down), Catch up tells the agent to run the missed trigger as soon as the runtime is back up. Example: If a task was scheduled for Monday at 9am and the machine was off until Tuesday at 10am, the agent runs the Monday task on Tuesday at 10am, then resumes the normal schedule.
Catch up only applies to recurring schedules, not one-time triggers. A missed one-time trigger is gone.

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Managing tasks

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Delivery channels

When a scheduled task finishes, the result is delivered to your configured channel: You can configure multiple delivery channels for a single task.

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Natural language scheduling

You can create a scheduled task by telling the agent in chat:
The agent parses the natural language schedule, creates the task in the Schedule, and confirms the details with you before saving.

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Use cases

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Important notes

Headmaster must be running for tasks to fire. Keep-awake helps but isn’t a service replacement — the runtime needs to be alive.
Prompts have full specialist + tools access — destructive prompts will run unsupervised in Autopilot. Test once in a manual conversation before scheduling.
  • Multiple tasks per conversation are allowed, but reusing one conversation for many tasks makes context noisy. Prefer separate conversations per recurring job.

Channels

Connect messaging platforms to receive scheduled task results.

Modes

Autopilot mode — how 24/7 scheduling works.