instruction-guardian

Instruction Guardian

A decision framework for routing content into the right destination and preventing re-bloat of instruction files.

Violating the letter of this skill is violating the spirit of it. If you find yourself reasoning that "this specific case is different" or "the skill didn't literally anticipate my situation, so the rule doesn't apply," stop — that reasoning is the failure mode this skill exists to catch.

When This Activates

You are about to call Edit or Write on:

• CLAUDE.md or AGENTS.md — at any path depth: the root file, or any nested instance (**/CLAUDE.md, **/AGENTS.md). Common layouts include apps/*/CLAUDE.md, packages/*/AGENTS.md, services/*/CLAUDE.md, but the trigger applies to any subdirectory location regardless of repo structure.
• MEMORY.md (append, update, or insert)
• Memory topic files under .claude/**/memory/ (e.g. ~/.claude/projects/<project-id>/memory/feedback_*.md, project_*.md, reference_*.md, user_*.md). These store the detailed content that MEMORY.md indexes — they are part of the auto-memory surface area and route by the same rules.
• Any file under .claude/rules/
• An @-import reference in any of the above

Or the user says:

• "add this to CLAUDE.md" / "document in AGENTS.md" / "update the agent instructions"
• "remember this" / "note this in the rules"

STOP. Run the checklist below before writing anything — regardless of edit size. A 1-line tweak, flag addition, typo fix, or appended list item all trigger the same checklist as a full rewrite.

Exception: approved instruction-cleanup Phase-3 plans

The one carve-out. When you are executing Edits that implement an already-approved instruction-cleanup Phase-3 plan, skip the per-Edit guardian checklist. Phase 2 of instruction-cleanup already applies the same litmus test ("would removing this cause the agent to make mistakes?"), routes each section through an equivalent flowchart, and has been explicitly approved by the user — that IS the guardian pass, done in batch form.

The carve-out is mechanized by a flag file. When instruction-cleanup Phase-3 begins, it creates a per-project flag in the system tmpdir; the PreToolUse hook checks for this flag and suppresses the reminder; Phase-3's last step removes the flag. The flag is intentionally outside the repo, so neither .gitignore nor commits ever need to mention it. In normal Phase-3 flow the carve-out happens automatically — you do not need to reason about it.

The bullets below are a safety net for cases the flag does not cover: hook disabled, flag missing because the cleanup skill was bypassed, an unusual conversation state, or a deviation discovered mid-implementation. In all of those, your judgment falls back to this checklist.

This exception is narrow:

• The plan must be approved by the user in the current conversation — not merely drafted or proposed.
• The Edit must match the plan as approved.
• Approval must be unambiguous and item-specific. If the user's response is hedged, partial, or scoped to a subset ("the rest is fine, let me think about X", "looks good overall", "start with the easy ones if you want"), only the explicitly approved items enter the carve-out. Every non-approved item still triggers guardian. When in doubt: not approved.
• Any deviation triggers guardian normally — scope creep, new sections the plan didn't cover, ad-hoc additions discovered mid-implementation, or content you decide to keep/move differently than the plan said. A deviating Edit should disarm the flag first (run the disarm snippet from instruction-cleanup's "Final step"), or accept that the hook will not fire for it.
• "I'm doing cleanup-ish work" is NOT the exception. The exception requires an explicit Phase-2 plan on record in this conversation.

For anything else — routine edits, multi-file fix sweeps, typo fixes, single-line tweaks — the full checklist still runs.

Rationalizations to catch in yourself

Applies to routine/ad-hoc edits. If you are inside an approved Phase-3 plan (see the Exception above), the carve-out controls — these rows describe bypasses for edits that are NOT part of such a plan.

Rationalization	Reality
"It's just N lines / a typo / one character"	Size is not the trigger. The trigger is the file. Run the checklist.
"I'm mid fix-sweep, this is just another file"	Instruction files have different health constraints than source files. Fix-mode doesn't exempt them.
"The subdirectory CLAUDE.md is less important than root"	Subdirectory instruction files still load in their scope and still re-bloat over time. Run the checklist.
"I already invoked the guardian earlier in this session"	Each edit is a separate routing decision. Past approval of a different edit does not transfer.
"The user explicitly told me to edit this file"	User tells you what they want; the guardian decides where it belongs. Explicit instruction does not bypass routing.
"The user said skip the checklist"	Acknowledge, then run it anyway — it costs seconds. If the guardian agrees the content belongs, you've lost nothing; if it doesn't, you've avoided a re-bloat commit.
"I've mentally walked through this already"	Mental checklist ≠ running the skill. Future edits skip the stored reasoning.
"The deploy/meeting/deadline is in N minutes"	The checklist takes seconds. Deadline pressure is exactly when skipped process steps become incidents.
"Guardian would obviously say yes — skipping saves a step"	Predicting the answer ≠ running the checklist. Predictions are wrong often enough that the seconds saved are not worth the routing miss.
"The rule can't have meant this edit"	The rule meant every edit. Constructing the exception IS the failure mode the spirit-vs-letter clause exists to catch.

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The Pre-Write Checklist

Before adding ANY content to an instruction file, answer these six questions in order:

1. How many lines is the file right now?

Check the current line count. If the file is already at or near the threshold, new content must be especially justified.

File type	Threshold	Action if over
CLAUDE.md / AGENTS.md	200 lines	Do NOT add. Extract or condense existing content first.
MEMORY.md	200 lines (hard limit — content past line 200 is invisible)	Move detailed content to topic files before adding.
.claude/rules/ file	No hard limit, but keep each file focused	Split into multiple files if growing large.

If adding this content would push the file over the threshold, you must extract or condense something else first. Never add to an over-threshold file without removing at least as much.

2. Is this already documented somewhere?

Before adding anything, check if the content (or equivalent) already exists in:

• The instruction file itself (duplicate entries degrade signal)
• Another instruction file at a different level (root vs subdirectory)
• A doc, skill, or rules file that already covers this topic
• The source code (comments, config files, .env.example)

If it's already documented, do NOT add it again. Duplication is worse than absence — it creates conflicting sources of truth.

3. Does removing this cause the agent to make mistakes?

This is the litmus test (from official Anthropic guidance). Apply it literally:

• "The agent would use getSession() instead of getUser() without this" — Yes, add it.
• "The agent wouldn't know our preferred test runner" — Yes, add it.
• "The agent wouldn't know the full Stripe checkout flow" — No. The agent can read the code.
• "The agent wouldn't know all our API endpoints" — No. The agent can read route files.

If the answer is no, the content does NOT belong in an instruction file. Route it elsewhere.

4. Where does this content belong?

digraph guardian {
  "New content" [shape=ellipse];
  "Fact needed every session?" [shape=diamond];
  "Removing causes mistakes?" [shape=diamond];
  "Multi-step procedure?" [shape=diamond];
  "Reference material?" [shape=diamond];
  "Shared convention?" [shape=diamond];

  "Instruction file\n(1-3 lines max)" [shape=box, style=bold];
  "Skill" [shape=box];
  "Separate doc" [shape=box];
  "Rules file" [shape=box];
  "Auto memory" [shape=box];
  "Do not persist" [shape=box];

  "New content" -> "Fact needed every session?";
  "Fact needed every session?" -> "Removing causes mistakes?" [label="yes"];
  "Removing causes mistakes?" -> "Instruction file\n(1-3 lines max)" [label="yes"];
  "Removing causes mistakes?" -> "Do not persist" [label="no"];
  "Fact needed every session?" -> "Multi-step procedure?" [label="no"];
  "Multi-step procedure?" -> "Skill" [label="yes"];
  "Multi-step procedure?" -> "Reference material?" [label="no"];
  "Reference material?" -> "Separate doc" [label="yes"];
  "Reference material?" -> "Shared convention?" [label="no"];
  "Shared convention?" -> "Rules file" [label="yes"];
  "Shared convention?" -> "Auto memory" [label="maybe"];
}

5. Is the format correct for the destination?

Each destination has format rules:

Instruction file (CLAUDE.md / AGENTS.md):

• One line per entry, two lines maximum
• No code blocks (extract to docs or skills)
• No tables over 5 rows (extract to docs)
• No full examples (extract to docs)
• Use "X not Y because Z" format for architecture decisions
• New references must use pitch-style: "Before doing X -> path/to/doc.md"

Skill (.claude/skills/):

• For procedures with 3+ steps
• Frontmatter (name + description) under 1024 chars total; aim for description under ~500 chars
• Description is just triggers, NOT the workflow (workflow summaries create shortcuts that agents follow instead of reading the skill body)
• Body loads only when invoked — can be detailed

Separate doc:

• For reference material the agent reads on demand
• Must be referenced from instruction file with a pitch-style pointer
• "Before adding a route -> docs/routes.md" (NOT just "docs/routes.md")

Rules file (.claude/rules/):

• For conventions scoped to file types
• Use paths: frontmatter to limit when they load
• One topic per file

Auto memory:

• For personal learned patterns and preferences
• Keep MEMORY.md as a concise index — details go in topic files
• Not for team-shared knowledge (use rules or instruction files instead)

6. Are you creating an @-import?

@-imports expand at launch. They load into context every session regardless of relevance.

NEVER create an @-import unless:
- The imported file is under 30 lines AND
- The content genuinely applies to every session AND
- There is no other way to share the content (e.g., importing AGENTS.md)

In almost all cases, use a pitch-style plain reference instead.

---

When the User Asks You to "Add This to CLAUDE.md"

The user may explicitly ask you to add content that doesn't belong in an instruction file. You should push back politely and suggest the right destination. You are a guardian of the instruction file's health.

How to push back:

"I'd rather not add this directly to CLAUDE.md — at [current line count] lines, we're [near/over] the 200-line target, and this [content type] would be better as [destination]. Here's what I'd do instead:

• [Specific routing suggestion]
• [One-liner for CLAUDE.md if applicable]

Want me to do that?"

When to comply anyway: If the user insists after you've explained the tradeoff, comply — but condense the content as much as possible and note the line count impact.

---

Condensation Patterns

When content does belong in an instruction file, condense it aggressively:

Gotchas/pitfalls — one line each:

# BAD (4 lines)
## Authentication
When using the auth middleware, always use `getUser()` instead of 
`getSession()`. The `getSession()` function doesn't verify JWT 
signatures with the auth server, which is a security risk.

# GOOD (1 line)
- Auth middleware: use `getUser()`, not `getSession()` — only `getUser()` verifies JWTs server-side

Architecture decisions — "X not Y because Z":

# BAD (3 lines)
We chose Prisma as our ORM. We evaluated Drizzle but decided against 
it because Prisma has a more mature migration system and the generated 
types work well with our TypeScript setup.

# GOOD (1 line)
- Prisma over Drizzle: mature migrations, Prisma Studio, generated types

Procedures — route to skill, leave pointer:

# BAD (15 lines of deployment steps in CLAUDE.md)

# GOOD (0 lines in CLAUDE.md — skill auto-discovers)
# Create .claude/skills/deploy/SKILL.md with the full procedure

---

Anti-Patterns to Catch

When you see these patterns being added to an instruction file, intervene:

Pattern	Problem	Route to
Full code block (>5 lines)	Burns context every session	Separate doc or inline in source
Table with 10+ rows	Reference material, not instructions	Separate doc
Step-by-step procedure	Procedure = verb = skill	.claude/skills/
API endpoint list	Agent reads route files	Separate doc (if needed at all)
Env var table	Agent reads .env.example	.env.example with comments
File tree	Agent uses file tools	Delete (or docs/structure.md for humans)
Version numbers	Change frequently, agent reads package files	Delete
Full configuration example	Reference material	Separate doc or inline in config
"For more details, see @large-file.md"	@-import expands at launch	Use pitch-style plain reference
Content duplicating what's in code	Agent can read the code	Delete