When do I clear the chat vs keep going?

A session is one continuous conversation with Claude — everything it can still see. Start a new session for a new task. Use /compact when a long thread is getting forgetful but isn't finished, and /clear when you're moving on to something unrelated.

If the context window is a million tokens, do I still need to manage sessions?

Yes — arguably more than before. A bigger window lets you run longer, but model performance still drifts as the window fills (context rot), and a long session collects clutter that competes for the model's attention. The window being large doesn't make a sprawling, unfocused context a good one.

What's the difference between /compact and /clear?

/compact asks Claude to summarize the session so far and keeps working on top of that summary — easy, but lossy, since Claude decides what mattered. /clear starts a fresh session with only the brief you write down — more effort, but the new context is exactly what you chose to keep. Reach for compact when continuity matters and the thread is clean; reach for clear when you're starting something new or the session has wandered.

When should I rewind instead of just correcting Claude?

When Claude has gone down a wrong path, rewind (double-tap Esc or /rewind) to just before it went wrong and re-prompt with what you learned, rather than piling a correction on top. Correcting leaves the failed attempt in the context as noise; rewinding removes it, so Claude starts clean from the better instruction.

How is this different from context engineering?

Context engineering is the concept — what the model can see when it answers, and why a focused window beats a bloated one. Session management is the hands-on practice of it inside Claude Code: the specific moves (continue, rewind, compact, clear, subagent) you use to keep that window in good shape. One is the why; this is the how.

Does /clear lose my progress?

Not your work (files on disk, anything you have already saved). It only clears the conversation context — the messages and file contents Claude is currently holding in memory. Your actual work is untouched.

How often should I /compact?

When a long session starts feeling sluggish or Claude seems to forget things you said earlier. That's usually a sign the context is full. /compact summarises it and makes room.

No. Once you clear, the conversation context is gone. If you might need continuity, use /compact instead — it preserves a summary.

Running a session well — Claude for Humans

A session is the whole conversation Claude can still see: every message you’ve sent, every file it has opened, every command it has run and what came back. Claude has no recollection of what you did last Tuesday — it has this thread. That is why “keep going or start fresh?” is a real decision with real consequences, rather than a matter of tidiness.

Space in that thread isn’t free. Everything sitting in it competes for the model’s attention, so a long session that has wandered through three unrelated tasks tends to get vaguer, slower, and more expensive than a short one pointed at the job in front of you. The two tools for that are opposites in a useful way: /clear throws the thread away and starts over, and /compact summarizes it and keeps working on top of the summary. If you’re unsure which you want, the comparison below is the one to read first — the short version is that clearing is right when the next thing is genuinely new, and compacting is right when the thread is still relevant but has grown heavy.

On Desktop most of this is clicking rather than typing. Opening a new chat is a clear, and your past conversations are sitting in the sidebar, so you resume one by clicking it. The two terminal commands below — claude -c and claude -r — exist to do what the sidebar already does for you, and belong to the Power Track; you can safely ignore them unless you’re working from a terminal.

The habit worth building is small: a new task deserves a new session. Starting clean keeps the dead ends and irrelevant file reads of the last job from bleeding into the next one, and it costs you nothing but one click. And when a session produced something you want to keep — a decision, a diagnosis, a piece of reasoning worth sharing — /export writes the whole exchange out to a file or your clipboard before you clear it away.

Commonly confused with

Two things people mix up here, and the difference that actually matters.

/clear vs /compact in Claude Code Both free up context space — but /clear is a fresh start and /compact is a summary that keeps the thread going. Picking the wrong one either loses useful context or keeps stale noise.

Session management in Claude Code: working well with a 1M context window A million-token context window is double-edged. It lets Claude work autonomously for longer, but it also gives clutter more room to accumulate. The skill is knowing, at each turn, whether to continue, rewind, compact, clear, or hand off to a subagent. 10 min

How to do it

What you want	On Desktop (no code)	Command line (Power Track)
Start a new task cleanly	Open a new chat, or clear the current one	`/clear`

/clear Wipe the conversation and start with a clean context window.
/compact Summarize the conversation so far to free up room — keeping the gist.
claude -c Pick up your most recent conversation right where you left off.
claude -r Reopen an earlier conversation from a list of your recent sessions.
/export Save the current conversation to a file or your clipboard.

Commonly confused with

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How to do it