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Approvals & human-in-the-loop

Headmaster keeps you in control. The agent asks for your approval before doing things that affect your files, your system, or external services.

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What triggers an approval

In Work Along mode, the agent asks before:
  • Running a tool — web search, code execution, file read/write, MCP call, image generation.
  • Accessing a file outside the project folder.
  • Making a network request — external API call, HTTP request, webhook.
  • Executing code — running a script, shell command, or code block.
In Run It Yourself mode, the agent runs tools without per-action approval but still asks before destructive actions:
  • Deleting a file.
  • Overwriting an existing file.
  • Sending an email or message.
  • Pushing to a remote (git push).
  • Running a command with sudo / admin privileges.
In Hands-Off and Autopilot, no approval prompts. All actions are logged.

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The approval prompt

When the agent wants to do something that needs approval, you see a card in the chat: 
The agent wants to run: web_search
Query: "latest Python release notes"

[Approve]  [Deny]  [Approve always for this conversation]
Click Approve to let it run. Click Deny to stop it. Click Approve always to let the agent run this tool type without asking again for the rest of this conversation.

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Clarification requests

Sometimes the agent needs more information before it can proceed. Instead of guessing, it asks you a question: 
The agent needs clarification:
"You mentioned 'the config file' — do you mean config.yaml or config.json?"

[config.yaml]  [config.json]  [Type your answer]
Click one of the suggested options, or type your own answer. The agent incorporates your response and continues.

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Permission requests

When the agent needs elevated permissions (e.g., sudo access to install a package), it sends a permission request: 
The agent needs sudo access to run: apt install postgresql-client

[Grant sudo for this command]  [Deny]
The request shows the exact command. You can grant sudo for this specific command only (not blanket sudo access).

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Secret requests

When the agent needs a secret (an API key, a password, a token) that it doesn’t have stored, it asks: 
The agent needs your Stripe API key to list recent charges.

[Enter key...]  [Skip]
The key you enter is stored in the Connections area (encrypted at rest) and is available to the agent in future conversations. You can revoke it any time.

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Audit trail

Every approval, denial, clarification, and permission grant is logged in the conversation transcript. The transcript shows:
  • What the agent requested.
  • What you approved or denied.
  • The timestamp.
  • The parameters of the action.
This audit trail is stored in the session file and can be exported for compliance reviews.