Conversations

A conversation (also called a chat) is where you work with Headmaster. This page covers starting, finding and organising chats, everything you can do in the message box, how to follow what the agent is doing, and how to tidy up afterwards.

Starting a chat

• Choose New Chat at the top of the sidebar, or type /new in the message box.
• Type what you need and press Enter to send. Press Shift+Enter for a new line.
• Headmaster gives the chat a title from your first message. You can rename it later.

A good first message says the goal and any limits. For example: "Draft a two paragraph reply to this email. Friendly, no jargon." See the examples further down.

The sidebar

Your chats are listed in the sidebar, newest first, grouped by date: Today, Yesterday, Previous 7 days, Last week, Earlier this month and older months.

Cloud chats and web chats share one list, so you can start a chat at headmaster.gcaplabs.com and carry on in the desktop app. See Web chat and Modes.

What the dots and labels mean

A chat in the list can show its state:

Label	Meaning
Session running	Headmaster is still working on this chat.
Needs your input	It is waiting for you, for example to approve an action.
Waiting for your answer	It asked you a question.
Finished, unread	It finished while you were elsewhere.
Background task running	A longer job it started is still going.
Draft, nothing sent yet	You typed something but did not send it.

This means you can start a long job, switch to another chat and come back when it shows as finished.

Pinning

Pinned chats stay at the top. Right click a chat and choose Pin, or Shift-click it. Choose Unpin to put it back in the normal list.

Searching

Use the Search box at the top of the sidebar to find a chat. If nothing matches you see "No chats match" with your search words. Choose Clear search to see all chats again.

Chat actions

Right click a chat in the sidebar (or use its actions menu) to see:

Action	What it does
Rename	Give the chat your own title. Leave it empty to clear it. You can also type /title.
Pin / Unpin	Keep it at the top of the list.
Mark as unread / Mark as read	Flag a chat to come back to.
Branch	Start a new chat that copies this one, so you can try a different direction without losing the original.
Export	Save the full chat as a JSON file on your computer.
Open in new tab / New window	Keep several chats open at once.
Archive	Hide the chat from the list without deleting it.
Delete	Permanently delete the chat. This cannot be undone.

Deleting a chat removes the conversation. It does not remove what Headmaster already saved to memory from it. See Memory.

The message box

Attaching things

Choose Attach (or drag files onto the chat, where you will see "Drop files to attach"). You can add:

• Files and Images from your computer.
• Paste image from your clipboard.
• Folder, to give Headmaster a whole folder to work with.
• URL. Headmaster fetches the page and uses it as context for that message.
• Prompt snippets, ready made starter prompts.

Each attachment shows as a chip you can preview or remove before sending. In the desktop app you can also type @ to reference files, folders and links inline.

Sending while Headmaster is working

You do not have to wait for a reply to finish.

• Queue message: what you type is held and sent as soon as the current reply ends. Queued messages show above the box. You can Edit, Delete or send one Next.
• Steer: send it now to redirect the reply in progress. Use this when you notice it heading the wrong way.
• Stop: ends the current reply. Queued messages pause, and you can choose Resume to send them.

Voice

• Voice dictation turns your speech into text in the box.
• Start voice conversation lets you talk back and forth. You can mute the microphone or end the conversation at any time.
• Read replies aloud speaks Headmaster's answers.

Helpful suggestions

As you type, Headmaster may offer a chip above the box:

• Schedule this, when your message sounds like something recurring. See Scheduled tasks.
• Add a connection, when you mention a service you could connect. See Connections and MCP servers.
• Use skill, when you mention a skill by name.

They are optional. Ignore them and your message is sent as typed.

Slash commands

Type / to see commands. The most useful:

Command	What it does
/new	Start a new chat.
/title	Rename this chat.
/retry	Send your last message again.
/undo	Remove your last message and its reply, then try again.
/branch	Branch the latest message into a new chat.
/compress	Shorten the chat's history so a long chat can continue.
/stop	Stop the current reply and any background work.
/copy	Copy the last reply.
/save	Save the chat to a JSON file.
/help	List the commands.

Following what Headmaster does

Headmaster does more than write text. It searches, reads files, runs commands and uses your connections. Each step appears in the chat as an expandable row, so you can see exactly what it did.

• Open a row to see the details, such as the search words, the file it read, or a command with its output and whether it succeeded.
• When a step needs your permission, the chat pauses and asks. Your approval setting decides when this happens. See Approvals.
• For multi step jobs Headmaster may keep a short to-do list, and the sidebar shows how many items are done.
• Files Headmaster creates, such as documents and charts, open in a preview next to the chat. You can also find them later under Artifacts in the sidebar.

Long chats

Every model can only read a certain amount of text at once. When a chat gets very long, Headmaster shortens older parts into a summary so the chat can keep going. You can also do this yourself with /compress.

If a chat has drifted a lot, starting a new one is often better. Headmaster still remembers the important facts through Memory.

Examples

Quick question. "What's a polite way to decline a meeting?" One message, one reply.

Working on a file. Attach a spreadsheet and ask "Find the three biggest costs and make a chart." Watch the tool rows as it reads the file, then open the chart in the preview.

Changing direction mid reply. Headmaster starts writing a long report but you wanted a summary. Type "Just a five line summary, please" and choose Steer.

Trying two approaches. You have a good draft but want to try a bolder version. Choose Branch, then ask for the bolder version in the new chat. The original stays as it was.

Tips

• One topic per chat keeps titles useful and context clean.
• Pin the chats you return to every day.
• Use Mark as unread as a quick "come back to this" flag.
• Export a chat before deleting it if you might need it later.

Troubleshooting

The message box says "Starting Headmaster" or "Reconnecting to Headmaster". Wait a moment. If it lasts more than a minute, check your internet connection.

A queued message did not send. You will see "Queued message not sent". It is still in the queue. Send it again.

A chat is missing from the list. Clear the search box, and check whether you archived it. For other problems see Troubleshooting.