Skip to main content

​
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.

​
Two execution modes

ModeWhat happens
New conversationEach run opens a fresh conversation with the result. Clean context every time.
Existing conversationThe result is appended into an existing conversation. Context keeps building across runs.
Managed from the Schedule page in the left sidebar — no chat command needed.

​
Creating a scheduled task

  1. Click The Schedule in the left sidebar.
  2. Click Create task.
  3. Fill in the form and click Save.

​
Task form fields

FieldDescription
Task nameDisplay name shown in the list
Agent + modelBackend agent and model (built-in, Claude Code, Codex, etc.)
SpecialistSpecialist persona to use
Workspace folderOptional working directory
FrequencyManual / Hourly / Daily / Weekdays / Weekly / Custom (cron)
TimeWhen to run (for daily/weekly/weekdays)
WeekdayFor weekly tasks
Cron expressionDirect cron when frequency = Custom
Execution modenew_conversation or existing
ModeAutopilot (no approvals) or Run It Yourself (approvals — but you won’t be there)
Delivery channelWhere to send the result (desktop, Telegram, email, webhook)
PromptMessage sent to the specialist when triggered
You can edit any task later by clicking it to open the detail page.

​
Schedule types

TypeHow to defineExample
Recurring scheduleCron expression0 9 * * * — every weekday at 9am
Fixed intervalEvery N minutes or hoursEvery 30 minutes
One-time triggerRun once at a specific time2026-07-01 at 14:00
For most schedules you don’t need to write cron — pick a frequency preset and Headmaster generates the expression for you.

​
Cron expression reference

Headmaster uses standard 5-field cron (no seconds field): 
┌───────── minute (0–59)
│ ┌─────── hour (0–23)
│ │ ┌───── day of month (1–31)
│ │ │ ┌─── month (1–12)
│ │ │ │ ┌─ day of week (0–6 or SUN–SAT)
│ │ │ │ │
* * * * *

​
Common examples

ExpressionMeaning
0 9 * * *Every day at 09:00
0 9 * * MONEvery Monday at 09:00
0 9 * * MON-FRIWeekdays at 09:00
0 * * * *Every hour on the hour
*/30 * * * *Every 30 minutes
0 */2 * * *Every 2 hours
0 0 1 * *1st of every month at midnight
0 18 * * FRIEvery Friday at 18:00

​
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.

​
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. This is what enables true 24/7 automation — your agent works while you sleep, while you’re in a meeting, or while your laptop is closed (as long as the machine is on and Headmaster’s runtime is running).

​
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.

​
The Schedule UI

The Schedule page shows:
  • Active tasks — tasks that are scheduled and will fire.
  • Paused tasks — tasks you’ve paused. They won’t fire until you resume them.
  • History — the last 50 runs, with timestamps, status (success, error, partial), and a link to the conversation transcript.
  • Next run — when each active task will next fire.

​
Managing tasks

  • Enable / Disable — toggle the switch on the task card.
  • Edit — click the task to open detail and change schedule, prompt, or model.
  • Delete — from the detail page (past runs are kept in history).
  • Run now — manually trigger from the detail page. Useful for testing a prompt before relying on the schedule.
  • Pause — temporarily stop a task without deleting it.
  • Resume — restart a paused task.

​
Delivery channels

When a scheduled task finishes, the result is delivered to the channel you configured:
ChannelHow
Desktop notificationSystem notification on your screen
TelegramMessage to your Telegram chat
EmailEmail to the configured address
WebhookPOST to a URL
Desktop chatNew message in your active conversation
You can configure multiple delivery channels for a single task.

​
Natural language scheduling

You can also create a scheduled task by telling the agent in chat: 
Every weekday at 9am, summarize my inbox and post the summary to Telegram.
The agent parses the natural language schedule, creates the task in the Schedule, and confirms the details with you before saving.

​
Use cases

Use caseFrequencyModePrompt
Daily summaryDaily 18:00new conversation”Summarize today’s commits across the repos in my workspace and post the highlights as a brief.”
Weekly reportWeekly, Mon 08:00existing”Draft this week’s progress report following last week’s structure, and flag anything blocked.”
Periodic reminderWeekdays 09:00new conversation”Remind me of the top 3 things on my plate today and ask one question that helps me prioritize.”
Recurring data pullHourlyexisting”Fetch the latest metrics from the dashboard MCP and append the deltas to this conversation.”
Inbox triageEvery 4 hoursnew conversation”Check my inbox via the email integration. Flag anything urgent. Draft replies for the rest.”
Nightly backupDaily 02:00new conversation”Back up the project folder to the S3 integration. Verify the upload succeeded.”

​
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.
  • Multiple tasks per conversation are allowed, but reusing one conversation for many tasks makes context noisy. Prefer separate conversations per recurring job.
  • Prompts have full specialist + tools access — destructive prompts will run unsupervised in Autopilot. Test once in a manual conversation before scheduling.
  • Catch up only applies to recurring schedules, not one-time triggers. A missed one-time trigger is gone.