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There’s a limit to how much your coworker can hold in mind at once. On a long task you’ll meet it, and it’s easy to handle.

The gauge

Next to the message box is a small ring showing how full things are getting. It’s green while there’s plenty of room, turns amber as it fills, and red when it’s nearly full. Watching it isn’t a chore — it just tells you when one of the options below is worth taking.
The context gauge shown green, amber and red as the conversation fills up

The same gauge at three points in a long task. Amber is the moment to consider compacting.

What to do when it fills

Three choices, in roughly the order you should consider them.
Click the ring, or type /compact. Your coworker summarises everything so far and carries on with the summary instead of the full history.Best when the task isn’t finished and the earlier detail no longer matters — a long research session where you’ve got what you need from the first twenty pages.The trade: it keeps the conclusions and loses the fine detail. If you might need something specific from earlier, save it to a file first.
Type /new. A fresh task, nothing carried over from the conversation.Best when you’ve moved on to a genuinely different job. Most “the conversation got too long” situations are actually two jobs in one task.Your coworker still has its instructions, skills and memory — you lose the conversation, not the coworker.
If the task is nearly done, just finish it. The gauge is a warning, not a wall.

Avoiding the problem

Put things in files, not in the chat. A file stays available at full detail regardless of how long the conversation gets. Pasting a large export into a message is the fastest way to fill the space up. One job per task. The most common cause of a very long conversation is three unrelated jobs sharing one. Ask for the summary before you need it. On a long research task, “summarise what you’ve found so far into a file” gives you something durable.
A long conversation isn’t a failure. Some jobs genuinely take hours. Compact when the gauge asks and carry on.

What carries between tasks

This trips people up, so plainly: So a new task doesn’t mean starting from nothing. Your coworker still knows who you are and how you like things — it just doesn’t have this particular conversation.

Common questions

No. The gauge shows you well before it matters, and compacting is a deliberate act — either yours or one it tells you about.
No. Files are untouched. Only the conversation is summarised.
Yes. A very long-running task may compact several times.
Ask your coworker to save it to a file, or tell it to remember — see What a coworker remembers.

Next steps

What a coworker remembers

What survives everything.

Managing your tasks

One job per task.

Files overview

Where to put the detail.

Slash commands

/compact and /new.