challenge

challenge is a skill for Claude Code, Codex from jaredlangleycc/nightshift-os. It costs 122 tokens per session (3,130 once invoked), scanned A, original, MIT.

A structured pre-mortem tool: before you commit to a major decision, it imagines that the plan failed and looks for what caused the failure.

In plain words
What is it for?
Use it to stress-test launches, hiring decisions, paid advertising, pricing changes, or plans to leave a job. It is not intended for emotional support or quickly reversible choices.
Why use it?
It exposes risks and weak points while they can still be discussed cheaply, before money, time, or reputation is committed.

Skill for Claude CodeCodex

Part of the nightshift-os plugin — 43 skills shipped together

Install

Getting it into your agent

One page per mod, every tool's command on it. A separate URL per tool would split the same page into five that compete with each other.

agentmods
npx agentmods add skills/jaredlangleycc/nightshift-os/challenge
Any agent
npx skills add jaredlangleycc/nightshift-os --skill challenge
Clone the repo
git clone --depth 1 https://github.com/jaredlangleycc/nightshift-os

Made for: Claude Code, Codex.

Or install nightshift-os, the plugin that ships this one along with the rest of its 43 skills.

Wrote this? Show the measurements

A badge with what this costs and how it scanned, read live from this page, so it follows the numbers instead of freezing them. Markdown for a README, HTML for a documentation site or a project page.

agentmods badge for challenge

README.md
[![agentmods](https://agentmods.dev/badge/skills/jaredlangleycc/nightshift-os/challenge.svg)](https://agentmods.dev/skills/jaredlangleycc/nightshift-os/challenge)
Your own site
<a href="https://agentmods.dev/skills/jaredlangleycc/nightshift-os/challenge"><img src="https://agentmods.dev/badge/skills/jaredlangleycc/nightshift-os/challenge.svg" alt="Measured on agentmods" height="20"></a>
Per session 122 Skills are progressive disclosure: only the name and description are preloaded; the body loads when the skill is used.
When invoked 3,130 The whole file, excluding the scripts and references it only reads on demand.
Security scan A 0 findings. Scan, not verified.
Origin original No closer match found in the catalogue.
Token cost

What it costs to keep this loaded

Counted locally with the o200k_base tokenizer, which is exact for GPT models; Claude uses its own tokenizer and its counts differ. Treat this as one consistent yardstick across the catalogue rather than a bill. Prices are per million input tokens.

ModelPer sessionOnce invoked
Fable 5 $0.00122 $0.03130
Opus 5 $0.00061 $0.01565
Sonnet 5 $0.00024 $0.00626
Haiku 4.5 $0.00012 $0.00313

Measured 4d ago against content hash dc7078d73e9d, method: parsed. Prices are Anthropic first-party input rates as of 2026-08-30, from the pricing page.

Security

Grade A, and why

challenge scanned grade A with 0 findings against 26 rules in 11 categories — prompt injection, anti-refusal, data exfiltration, privilege escalation, supply chain, agent snooping, system-prompt leakage, SSRF and excessive agency — measured 4d ago.

A static scan of the body, not an audit. Every finding is printed with the line that produced it so you can judge whether it matters here. A mod is markdown that instructs an agent; that is exactly why what it instructs is worth reading.

Nothing flagged

None of the 26 patterns this scan looks for appear in this file: no shell pipes, no recursive deletes, no credential paths, no hidden text, no instruction-override or anti-refusal phrasing, no agent-config snooping. That is not a guarantee, it is the absence of the things that are checkable.

skills/coach/challenge/SKILL.md · 246 lines

How it starts

The opening of the file, as written. The whole thing — 246 lines — stays where its author put it; the contents beside it link to each section on GitHub.

Challenge

The pre-mortem. Before the user locks a decision, imagine it failed and ask what killed it. Find the holes while the cost of finding them is only an awkward 20-minute conversation.

Working-parent solopreneurs cannot afford to learn from a bet that quietly failed in the background while they were at soccer practice. This skill makes the failure modes audible.

When this skill triggers

Fire when the user:

  • Says "challenge me on X"
  • Says "challenge this plan"
  • Says "pre-mortem this"
  • Says "stress-test this"
  • Says "what could go wrong"
  • Says "find the holes"
  • Says "play devil's advocate"
  • Is about to lock a decision via decision-logger that involves real money, real time, or real reputation risk
  • Has presented a plan and the implicit signal is "tell me this is OK"

Do not fire when:

  • The user is in hard-call mode (different posture: hard-call holds ambiguity, challenge breaks a plan)
  • The user is asking for emotional support (route differently, the challenge skill is for analytical critique)
  • The decision is reversible within 7 days (e.g., subscribing to a free tool)

The pre-mortem sequence

Six steps. Do not skip.

Step 1: State the plan in one sentence

Force the user to name the plan precisely. If they cannot, the plan does not exist yet.

Bad: "I'm thinking about doing some outbound." Good: "I'm going to send 50 cold emails per day to new sales managers at B2B SaaS 50-500, using the 3-angle sequence I drafted on May 18, starting Mon June 15."

The pre-mortem operates on the specific plan. Vague plans cannot be stress-tested.

Step 2: Skip 6 months. Imagine it failed.

Project the user 6 months forward. The plan ran. It failed. They are looking back.

Ask: "It's December. The plan you locked today did not work. What's the headline of the post-mortem?"

Let them name it. Then ask: "And underneath the headline, what are the 3 things that went wrong?"

The pre-mortem operates from a future-failed perspective. This is the structural move that makes the skill different from generic risk analysis.

Read the full file on GitHub · 246 lines

Files

What ships with it

2 files beside SKILL.md in the same directory: the scripts, references and assets a skill reads on demand. Not counted in the per-session cost; read them before you install if any of them is executable.

Changes

What this file has done since we first saw it

Hashed on every crawl. A supply-chain change to an agent config is a question of when, not whether, so the history is kept rather than the latest state alone.

  1. 4d ago First seen · 246 lines · 122 tokens per session scan A dc7078d73e9d

Subscribe to this mod's changes

challenge is a skill published in the GitHub repository jaredlangleycc/nightshift-os (3 stars, last pushed 1mo ago), licensed MIT. It adds 122 tokens to every session and 3,130 once invoked, about $0.0006 per session on Opus 5. A static security scan graded it A with 0 findings. No closer match exists in the catalogue, so it is treated as the original; first seen 2026-08-31.

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