Skip to main content

​
Getting started

Setup time: about 5 minutes from download to your first conversation.

​
System requirements

PlatformMinimumRecommended
macOS10.14 (Mojave)12.0+ (Monterey)
Windows1011
LinuxUbuntu 18.04+Ubuntu 22.04+
Memory4 GB RAM8 GB RAM
Storage500 MB2 GB (for workspace + agent data)

​
Download and install

​
Windows

  1. Download the installer (.exe) from the Headmaster site.
  2. Run the installer. Headmaster installs to the standard location and creates a desktop shortcut.
  3. Or: download the portable .zip, extract to any folder, and run Headmaster.exe directly. No admin rights needed.

​
macOS

Homebrew (recommended) 
brew install headmaster
Direct download
  1. Download the .dmg file from the Headmaster site.
  2. Open the .dmg, drag Headmaster to Applications.
  3. On first launch, macOS may warn about an unidentified developer. Right-click → Open to bypass.

​
Linux

.deb package 
sudo dpkg -i Headmaster-<version>-linux-amd64.deb
.AppImage 
chmod +x Headmaster-<version>-linux-x86_64.AppImage
./Headmaster-<version>-linux-x86_64.AppImage
Method 3: Homebrew (Linuxbrew) 
brew install headmaster

​
First launch

On first launch, Headmaster:
  1. Starts the local runtime — the background service that runs your agents. This takes a few seconds. You’ll see a splash screen while it initializes.
  2. Opens the main window. You’ll see a sidebar with your conversations and a chat composer at the bottom.
  3. Walks you through one-time setup. Pick a default model, and (optionally) sign in to a model provider. You can skip this and do it later.
You do not need to configure anything else to send your first message. If you already have a CLI agent installed (Claude Code, Codex, Gemini CLI, etc.), Headmaster auto-detects it and lights it up on the welcome screen. The default experience uses Headmaster’s built-in agent — ready to use immediately. No external CLI needed. See Your Crew if you want to connect external CLI agents.

​
Connect a model provider

The built-in agent needs at least one model provider before it can chat. Add an API key:
  1. Click Settings in the left sidebar.
  2. Open Headmaster’s Library → Connections.
  3. Click Add provider and pick one — supported: Gemini, OpenAI, Anthropic, DeepSeek, OpenRouter, and 25+ more.
  4. Paste your API key and save.
Multi-key rotation: Paste multiple API keys (comma-separated or one per line). Headmaster auto-rotates and skips invalid or rate-limited keys. See Models & providers for details.
The Connections area is PIN-protected. The default PIN is set on first run. You can change it any time in Headmaster’s Library → Advanced → Change PIN. Already using a CLI agent? Claude Code, Codex, Gemini CLI, etc. are detected automatically — no extra setup needed. They appear on the welcome screen alongside the built-in agent.

​
Send your first message

​
Create a new conversation

  1. Click New chat in the left sidebar.
  2. Pick an agent — built-in (default) or any detected CLI agent on the welcome screen.
  3. Pick a model — use the selector at the bottom-left of the input box. Each agent has its own model list.
  4. Pick a specialist (optional) — a pre-configured persona. See Specialists.
  5. Type your message and press Enter.

​
Try these prompts

Hello, please introduce yourself.

Help me write a Python function to calculate the Fibonacci sequence.

Please analyze the contents of this file.
The agent streams its response into the chat. Tool calls (web searches, file reads, code execution) appear as expandable blocks.

​
Explore the built-in tools

​
File upload

  • Drag and drop into the input box.
  • Pick from disk: click the + button to choose files or folders.
  • Supported: text files, images, code, PDFs, Office documents.

​
Multiple conversations

  • New conversation: click New chat.
  • Switch: pick any conversation in the left history list — each has independent memory.
  • Search: type in the search bar to filter conversations by title or content.

​
Project (working folder)

  • Open a project: click the + button → Open folder.
  • Workspace panel: appears on the right with the folder tree once opened.
  • Quick file picking: browse and attach files directly from the panel.
  • Locked per conversation: the folder cannot change mid-conversation — start a new chat for a different folder.

​
Undo

  • Back up recent turns. Edit a message and re-send. The conversation continues from the edited point.

​
Approvals

When the agent wants to run a tool or access a file, it asks for your approval in the chat. Click Approve or Deny. See Approvals & human-in-the-loop.

​
Specialists

20+ built-in assistants, each with a specific role. Pick one from the specialist picker. See Specialists.

​
First launch FAQ

I don’t see any models after launch. Open Settings → Headmaster’s Library → Connections and add at least one provider’s API key. If a CLI agent is installed, it’s auto-detected on the welcome page — you can use it without adding a key. Image generation isn’t working. Check:
  • Image generation is enabled in Settings → Advanced → Tools.
  • A model supporting image generation is selected.
  • See Image generation for the full configuration guide.
How do I switch between AI models? Use the model selector at the bottom-left of the input box. Each agent (built-in, Claude Code, Codex, etc.) exposes its own model list — switching the agent also switches the model list. Where are my conversations stored? All local:
  • macOS: ~/Library/Application Support/Headmaster/
  • Windows: %APPDATA%\Headmaster\
  • Linux: ~/.config/Headmaster/
The runtime won’t start. Check <data folder>/logs/<today>.log for the startup error. Most common: a port conflict or a missing system dependency on Linux. See Troubleshooting.

​
Next steps

TopicLink
LLM configurationModels & providers
Multi-agent modeYour Crew
SpecialistsSpecialists
MCP configurationConnections (MCP)
WebUI / remote accessHeadmaster on the Go
Scheduled tasksThe Schedule
ChannelsChannels
Image generationImage generation
Use casesUse cases & user stories
FAQFAQ