By name: ring:testing-skills-with-subagents description: "Hardening a skill so it resists rationalization under pressure: run combined-pressure scenarios on a subagent without the skill (RED), capture excuses verbatim, write/edit the skill (GREEN), then plug loopholes (REFACTOR) until compliance holds. Use when deploying or editing a discipline-enforcing skill that an agent could rationalize away. Skip for pure reference skills with no rules to violate."
Testing Skills With Subagents
When to use
- Before deploying a new skill
- After editing an existing skill
- Skill enforces discipline that could be rationalized away
Skip when
- Pure reference skill → no behavior to test
- No rules that agents have incentive to bypass
Related
Complementary: ring:writing-skills, ring:test-driven-development
Testing skills is TDD applied to process documentation.
Run scenarios without the skill (RED — watch agent fail), write skill addressing those failures (GREEN), then close loopholes (REFACTOR).
Prerequisite: Understand ring:test-driven-development first. Complete worked example: examples/CLAUDE_MD_TESTING.md.
When to Test
Test skills that: enforce discipline (TDD, testing requirements), have compliance costs (time, effort, rework), could be rationalized away ("just this once"), or contradict immediate goals (speed over quality).
Skip: Pure reference skills (API docs), skills without rules to violate.
TDD Mapping
| TDD Phase | Skill Testing | What You Do |
|---|---|---|
| RED | Baseline test | Run scenario WITHOUT skill, watch agent fail |
| Verify RED | Capture rationalizations | Document exact failures verbatim |
| GREEN | Write skill | Address specific baseline failures |
| Verify GREEN | Pressure test | Run WITH skill, verify compliance under pressure |
| REFACTOR | Plug holes | Find new rationalizations, add counters |
RED Phase: Watch It Fail
Run 3+ combined-pressure scenarios WITHOUT the skill. Document agent choices and rationalizations word-for-word.
Why verbatim? Exact wording reveals the loopholes to close.
Writing Pressure Scenarios
| Quality | Example |
|---|---|
| Bad | "What does the skill say?" — agent recites |
| Good | "Production down, $10k/min, 5min window" — single pressure |
| Great | "3hr/200 lines done, 6pm, dinner plans, forgot TDD. A) Delete B) Commit C) Tests now" — multi-pressure + forced choice |
Pressure types: Time (deadline), sunk cost (hours invested), authority (senior says skip), economic (job at stake), exhaustion (end of day), pragmatic ("being realistic").
Best tests combine 3+ pressures.
GREEN Phase: Write Minimal Skill
Address the specific failures documented in RED. Don't add hypothetical content — write just enough to address actual observed failures. Re-run same scenarios WITH skill; agent should now comply.
REFACTOR Phase: Close Loopholes
Agent still violated rule despite having the skill? Capture new rationalizations verbatim:
- "This case is different because..."
- "I'm following the spirit not the letter"
- "Being pragmatic means adapting"
For each rationalization, add: explicit negation rule, rationalization table entry, red flag entry.
Meta-test: "You read the skill and chose wrong anyway. How could the skill have been written to make the right answer the only acceptable one?"
Continue REFACTOR until no new rationalizations appear.
Signs of Bulletproof Skill
- Agent chooses correct option under maximum pressure
- Agent cites skill sections as justification
- Agent acknowledges temptation but follows rule anyway
- Meta-test reveals "skill was clear, I should follow it"
Real-World Impact
From applying TDD to TDD skill itself:
- 6 RED-GREEN-REFACTOR iterations to bulletproof
- 10+ unique rationalizations discovered
- Each REFACTOR closed specific loopholes
- Final: 100% compliance under maximum pressure