# Challenge

> Challenge, push back, play devil's advocate on AI output. Use when: challenge this, are you sure, push back, prove it, what if you're wrong, devil's advocate, stress test, poke holes, second opinion, sanity check, too confident, really?, question this decision. Subcommands: anchor (committed too fast), verify (facts wrong?), framing (wrong problem?), deep (full devil's advocate in separate contex…

- **Type:** Skill
- **Install:** `agentstack add skill-digital-stoic-org-agent-skills-challenge`
- **Verified:** Yes — security-reviewed for prompt injection and unsafe behavior
- **Seller:** [digital-stoic-org](https://agentstack.voostack.com/s/digital-stoic-org)
- **Installs:** 0
- **Category:** [Agent Skills](https://agentstack.voostack.com/c/agent-skills)
- **Latest version:** 0.1.0
- **License:** MIT
- **Upstream author:** [digital-stoic-org](https://github.com/digital-stoic-org)
- **Source:** https://github.com/digital-stoic-org/agent-skills/tree/main/cognitive/skills/challenge

## Install

```sh
agentstack add skill-digital-stoic-org-agent-skills-challenge
```

Requires the [AgentStack CLI](https://agentstack.voostack.com/docs/cli). Works with Claude Code, Cursor, and any MCP-compatible agent.

## About

# Challenge

Apply structured provocation patterns to force reconsideration of current work.

**Target:** **$ARGUMENTS**

## ⚠️ AskUserQuestion Guard

**CRITICAL**: After EVERY `AskUserQuestion` call, check if answers are empty/blank. Known Claude Code bug: outside Plan Mode, AskUserQuestion silently returns empty answers without showing UI.

**If answers are empty**: DO NOT proceed with assumptions. Instead:
1. Output: "⚠️ Questions didn't display (known Claude Code bug outside Plan Mode)."
2. Present the options as a **numbered text list** and ask user to reply with their choice number.
3. WAIT for user reply before continuing.

## Dispatch

Parse first word of $ARGUMENTS as subcommand:

| Subcommand | Error Type | Protocol |
|---|---|---|
| `anchor` | Premature commitment / anchoring bias | Read `protocols/anchor.md` → execute |
| `verify` | Factual errors / hallucination | Read `protocols/verify.md` → execute |
| `framing` | Wrong problem / framing errors | Read `protocols/framing.md` → execute |
| `deep` | High stakes — all 9 patterns in fresh context | Spawn devil-advocate sub-agent via Agent |

## No-Subcommand Fallback

If no subcommand detected:

AskUserQuestion: "What are you worried about with the current AI response?"
- A) Anchoring bias — AI committed too early to one approach
- B) Factual accuracy — claims may be wrong or hallucinated
- C) Wrong framing — solving the wrong problem
- D) High stakes — want all 9 patterns in fresh context (Devil's Advocate)

→ Dispatch to matching subcommand based on answer.

## Deep Subcommand

Spawn via Agent tool:
- subagent_type: `dstoic:devil-advocate:devil-advocate`
- prompt: target description + relevant file paths to read
- The agent runs ALL 9 patterns (anchor: Gatekeeper, Reset, Alt Approaches, Pre-mortem · verify: Proof Demand, CoVe, Fact Check List · framing: Socratic, Steelman) comprehensively in fresh context
- DO NOT pass parent conversation reasoning — fresh context is the point

## Thinking Transparency (applies to all subcommands)

For every finding, make reasoning explicit:

1. **Observation**: What specifically in the target triggered this finding
2. **Technique family**: Which challenge family (anchor/verify/framing) and named pattern (e.g., Gatekeeper, CoVe, Steelman) — cite mechanism from `reference.md` pattern catalog
3. **Reasoning**: Why this observation matters — what cognitive bias or error it reveals
4. **Confidence**: How certain is this finding (High/Medium/Low) and what evidence supports that rating

## Output

All subcommands produce a **Challenge Report** (structured, not prose).
See `reference.md` for report format and pattern catalog.

## Source & license

This open-source skill is cataloged on AgentStack and links to its original source — we do not rehost the code.

- **Author:** [digital-stoic-org](https://github.com/digital-stoic-org)
- **Source:** [digital-stoic-org/agent-skills](https://github.com/digital-stoic-org/agent-skills)
- **License:** MIT

Install and usage instructions live in the source repository linked above.

## Pricing

- **Free** — Free

## Security capabilities

Automated source analysis of v0.1.0 — what this tool can access:

- **Network access:** no
- **Filesystem access:** no
- **Shell / process execution:** no
- **Environment & secrets:** no
- **Dynamic code execution:** no

*"Yes" means the capability is present in the source — more access means more to trust, not that it is unsafe.*


## Versions

- **0.1.0** — security scan: passed — Imported from the upstream source.

## Links

- Listing page: https://agentstack.voostack.com/l/skill-digital-stoic-org-agent-skills-challenge
- Seller: https://agentstack.voostack.com/s/digital-stoic-org
- Browse the marketplace: https://agentstack.voostack.com/browse

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