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Lesson 067

You Should Know: A Side Agent That Watches for What You'd Miss

2026-10-05
you-should-knowpluginsworkflow
Quick Quiz
What does Claude Code's built-in "You Should Know" plugin actually run, and what does it require to work?
Click to reveal answer
It runs a separate side agent, alongside your main session, that scans the transcript for decisions or details you might overlook and posts a note above the prompt when it finds one. It's opt-in, disabled by default, and only works for first-party sessions with telemetry turned on.

A second agent, watching the first one

When Claude Code works through a long task — a multi-file refactor, a dependency bump, a migration — a lot happens between the prompt you typed and the summary it gives you at the end. Assumptions get made. Edge cases get silently skipped. A flag gets flipped that you'd want to know about. Most of that scrolls past in the output, and unless you read every line, you miss it.

You Should Know is a built-in Claude Code plugin, shipped in v2.1.287 (October 1, 2026), that addresses this directly. Instead of trying to make the main agent narrate everything, it spins up a separate side agent whose only job is to watch the main agent's work and flag things worth your attention. When it spots something, it drops a note in a banner above your prompt — not buried in the transcript, not something you have to scroll back for.

Enabling it

The plugin ships disabled by default. Turn it on with:

/plugin enable cc-plugin-you-should-know@builtin

It's also visible in the /plugin panel under Installed → Show disabled sections. Two requirements worth knowing before you flip it on: it only runs on first-party Claude sessions, and it requires telemetry to be enabled, since the side agent's observations are part of that data path. If either condition isn't met, the plugin stays dormant even if "enabled."

What it's good for

It's not a substitute for reviewing diffs or reading plans — it's a safety net for the stuff that's easy to miss when you're trusting Claude to handle the toil.

Key Takeaway

Enable cc-plugin-you-should-know@builtin for long tasks — it's a second agent dedicated to catching what you'd otherwise scroll past, but it needs telemetry on and only works in first-party sessions.