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Data, privacy & security

Headmaster is designed to be local-first. Your data lives on your machine.

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What’s stored locally

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What’s sent to providers

When the agent calls a model provider (Anthropic, OpenAI, Google, etc.): Sent:
  • 💬 Your message text
  • 📜 The conversation history (current session only)
  • 📎 Any file contents the agent read into context
  • 🧠 The system prompt (specialist personality, memory facts, skill instructions)
Not sent:
  • 🔑 Your API keys for other providers
  • 📁 Your full file system (only files explicitly read into context)
  • 📂 Other conversation transcripts
  • 🚫 Memory facts not relevant to the current turn

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What’s sent to external services

When the agent calls a tool (MCP server, integration, web search), the parameters of that call are sent to the service. The agent only calls tools you’ve approved (in Work Along mode) or that are on the allowed list (in other modes).

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Encryption

Memory needs to be readable by the runtime, so it’s not encrypted at rest. For full encryption, use FileVault (macOS), BitLocker (Windows), or LUKS (Linux) for full-disk encryption.

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Remote mode privacy

In remote mode, your data lives on the machine running the runtime. The desktop app is a thin client — it renders the UI and forwards your input. The runtime machine sees your messages, conversation history, agent responses, and your stored provider keys.
Only connect to a runtime on a machine you control. Don’t connect to a runtime on a machine you don’t trust.

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Data migration

To move your Headmaster data to a new machine:
1

Quit Headmaster on the old machine

Make sure the app is fully closed before copying.
2

Copy the data folder

Copy the entire data folder to the new machine.
3

Install Headmaster on the new machine

Install the desktop app.
4

Place the data folder

Put it in the correct location for the new OS (see paths below).
5

Launch Headmaster

All your conversations, memory, settings, skills, and extensions are preserved.

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Clean uninstall

To completely remove Headmaster and all its data:
1

Quit Headmaster

Close the app fully.
2

Delete the application

Drag to Trash on macOS, uninstall from Settings on Windows, or remove the package on Linux.
3

Delete the data folder

  • Windows: %APPDATA%\Headmaster
  • macOS: ~/Library/Application Support/Headmaster
  • Linux: ~/.config/Headmaster
4

Windows only: remove the registry key

Delete HKEY_CURRENT_USER\Software\Headmaster.
This removes everything permanently — conversations, memory, settings, logs, skills, and extensions. It cannot be undone.

Security & approvals

Approval gates, container isolation, and credential storage details.

Runtime settings

Configure local vs. remote runtime connections.