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Bitterpillengineering

  • 34 installs
  • 17.2k repo stars
  • Updated August 1, 2026
  • danielmiessler/personal_ai_infrastructure

Audits AI instruction sets for over-prompting, classifying each rule as cut, merge, sharpen, or keep and estimating token savings.

About

Applies the test 'would a smarter model make this rule unnecessary?' via Five Questions, classifying each rule and reporting estimated line and token savings across a full setup or a single file. Developers use it to trim CLAUDE.md and instruction files for better output.

  • Five Questions test with CUT/RESOLVE/MERGE/SHARPEN/KEEP classification
  • Reports estimated line and token savings

Bitterpillengineering by the numbers

  • 34 all-time installs (skills.sh)
  • Ranked #8,855 of 16,546 AI & Agent Building skills by installs in the Skillselion catalog
  • Data as of Aug 5, 2026 (Skillselion catalog sync)
npx skills add https://github.com/danielmiessler/personal_ai_infrastructure --skill bitterpillengineering

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Listed on Skillselion
Installs34
repo stars17.2k
Last updatedAugust 1, 2026
Repositorydanielmiessler/personal_ai_infrastructure

What it does

Audits AI instruction sets for over-prompting, classifying each rule as cut, merge, sharpen, or keep and estimating token savings.

Files

SKILL.mdMarkdownGitHub ↗

Customization

Before executing, check for user customizations at: ~/.claude/PAI/USER/SKILLCUSTOMIZATIONS/BitterPillEngineering/

If this directory exists, load and apply any PREFERENCES.md, configurations, or resources found there. These override default behavior. If the directory does not exist, proceed with skill defaults.

Voice Notification

When executing a workflow, do BOTH:

1. Send voice notification:

   curl -s -X POST http://localhost:31337/notify \
     -H "Content-Type: application/json" \
     -d '{"message": "Running the WORKFLOWNAME workflow in the BitterPillEngineering skill to ACTION"}' \
     > /dev/null 2>&1 &

2. Output text notification:

   Running the **WorkflowName** workflow in the **BitterPillEngineering** skill to ACTION...

BitterPillEngineering

Audit any AI instruction set for over-prompting. Based on the principle that less scaffolding = better output — every unnecessary rule competes for attention and degrades the rules that matter.

The core test: "Would a smarter model make this unnecessary?" If yes, it's scaffolding, not architecture.

Workflow Routing

WorkflowTriggerFile
Audit"audit setup", "full audit", "check all rules"Workflows/Audit.md
QuickCheck"quick check", "check this file", "check these rules"Workflows/QuickCheck.md

Examples

Example 1: Full system audit

User: "Run BPE on my setup"
→ Invokes Audit workflow
→ Reads all force-loaded files from settings.json
→ Evaluates each rule against the Five Questions
→ Returns categorized report with estimated token savings

Example 2: Check a single file

User: "Quick check this CLAUDE.md"
→ Invokes QuickCheck workflow
→ Reads the target file
→ Returns concise keep/cut/sharpen verdict

Example 3: Post-cleanup validation

User: "I trimmed my rules, check if anything's still redundant"
→ Invokes Audit workflow
→ Compares remaining rules against Claude defaults
→ Flags any surviving dead weight

Gotchas

  • Claude's built-in system prompt changes across versions — what was "default behavior" 3 months ago may not be now. When in doubt, test rather than assume.
  • Rules that seem redundant with defaults may have been added because Claude was inconsistent about following the default. Check failure history before cutting.
  • "One-off fix" rules sometimes prevent recurring failures. Check if the failure pattern is truly gone before removing.
  • The loadAtStartup list in settings.json and postCompactRestore.fullFiles must stay in sync — if you remove a file from one, check the other.

The Five Questions

For every rule, instruction, or preference found, evaluate:

1. Default behavior? Does Claude already do this without being told? 2. Contradiction? Does this conflict with another rule in the same or different file? 3. Redundancy? Is this already covered by a different rule or file? 4. One-off fix? Was this added to fix one specific bad output rather than improve outputs generally? 5. Vague? Would Claude interpret this differently every time? (e.g., "be more natural", numeric personality scales)

Classification

CategoryAction
Restates default behaviorCUT — the model already does this
Contradicts another ruleRESOLVE — pick one, cut the other
Duplicates another ruleMERGE — one location, one statement
One-off fix for past mistakeEVALUATE — still relevant or already learned?
Vague / unquantifiableSHARPEN — add specific DO/DON'T examples, or cut
Loaded but rarely actionableMOVE to on-demand — load via CONTEXT_ROUTING when needed
Specific, actionable, non-defaultKEEP — this is what good instructions look like

Anti-Fragile vs Fragile

Keep (anti-fragile): Verification harnesses, ISC, data pipelines, specific DO/DON'T examples, tool preferences, routing rules.

Cut (fragile): CoT orchestrators, format parsers, retry cascades, numeric personality scales, abstract value statements, process descriptions that aren't followed.

Output Format

## BitterPillEngineering Audit

**Scope:** [what was audited]
**Files read:** [count]
**Rules evaluated:** [count]

### CUT (restating defaults)
- [rule] — [reason]

### RESOLVE (contradictions)
- [rule A] vs [rule B] — [which to keep and why]

### MERGE (redundancies)
- [locations] — [merge into where]

### EVALUATE (one-off fixes)
- [rule] — [still needed? verdict]

### SHARPEN or CUT (vague)
- [rule] — [sharpen how, or cut why]

### MOVE to on-demand
- [content] — [how often it's actually needed]

### KEEP (carrying weight)
- [rule] — [why it matters]

**Estimated savings:** [lines] lines, ~[tokens] tokens

Execution Log

After completing any workflow, append a single JSONL entry:

echo '{"ts":"'$(date -u +%Y-%m-%dT%H:%M:%SZ)'","skill":"BitterPillEngineering","workflow":"WORKFLOW_USED","input":"8_WORD_SUMMARY","status":"ok|error","duration_s":SECONDS}' >> ~/.claude/PAI/MEMORY/SKILLS/execution.jsonl

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