obsidian-challenge

obsidian-challenge is a command for Claude Code from eugeniughelbur/obsidian-second-brain. It costs 20 tokens per session (772 once invoked), scanned A, original, MIT.

A command that tests a current idea or plan against notes stored in an Obsidian vault. It looks for earlier decisions, failures, contradictions, and risks that may challenge the idea.

In plain words
What is it for?
Red-teaming plans, checking proposed designs, finding lessons from previous work, and identifying contradictions in project notes.
Why use it?
It helps reveal assumptions that conflict with past experience before they lead to another failed approach.

Command for Claude Code

Written for Claude Code: $ARGUMENTS substitution. Also seen: mentions subagents.

Part of the obsidian-second-brain plugin — 1 skill, 47 commands, 3 hooks shipped together

Good fit Red-teaming plans, checking proposed designs, finding lessons from previous work, and identifying contradictions in project notes.

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Install with agentmods
npx agentmods add commands/eugeniughelbur/obsidian-second-brain/obsidian-challenge
About the project

obsidian-second-brain turns an Obsidian vault into persistent, searchable memory for Claude Code and other command-line coding agents, storing knowledge as linked Markdown notes. It is for developers, founders, writers, and researchers who want agents to retain project context across sessions. Its catalogue entries provide commands, hooks, a plugin, a skill, and instructions for capturing, finding, and maintaining that memory.

eugeniughelbur/obsidian-second-brain · 4,376 stars · on GitHub · eugeniughelbur.github.io

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.

Clone the repo
git clone --depth 1 https://github.com/eugeniughelbur/obsidian-second-brain

Made for: Claude Code.

Or install obsidian-second-brain, the plugin that ships this one along with the rest of its 1 skill, 47 commands, 3 hooks.

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 obsidian-challenge

README.md
[![agentmods](https://agentmods.dev/badge/commands/eugeniughelbur/obsidian-second-brain/obsidian-challenge/github.svg)](https://agentmods.dev/commands/eugeniughelbur/obsidian-second-brain/obsidian-challenge)
Your own site
<a href="https://agentmods.dev/commands/eugeniughelbur/obsidian-second-brain/obsidian-challenge"><img src="https://agentmods.dev/badge/commands/eugeniughelbur/obsidian-second-brain/obsidian-challenge/github.svg" alt="Measured on agentmods" height="20"></a>

Or the 80×15 button, for a site that already has a row of RSS and ATOM ones. Only the verdict fits; the numbers stay here.

agentmods 80×15 button for obsidian-challenge

Your own site · 80×15
<a href="https://agentmods.dev/commands/eugeniughelbur/obsidian-second-brain/obsidian-challenge"><img src="https://agentmods.dev/badge/commands/eugeniughelbur/obsidian-second-brain/obsidian-challenge.svg" alt="Reviewed on agentmods" width="80" height="20"></a>
Per session 20 Only the description is in the session, so the agent can decide to use it. The body loads when it is invoked.
When invoked 772 The whole file, excluding the scripts and references it only reads on demand.
Security scan A 0 findings. A grade says what 26 rules found in the file — not that it is safe.
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 5.1 $0.00020 $0.00772
Opus 5 $0.00010 $0.00386
Sonnet 5 $0.00004 $0.00154
Haiku 4.5 $0.00002 $0.00077

Measured 10d ago against content hash 277115ffa8c8, method: parsed. Prices are Anthropic first-party input rates as of 2026-09-10, from the pricing page.

Security

Grade A, and why

obsidian-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 10d 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.

commands/obsidian-challenge.md · 36 lines

What it actually says

Use the obsidian-second-brain skill. Execute /obsidian-challenge $ARGUMENTS:

The optional argument is the idea, belief, or plan to challenge. If not provided, infer the user's current position from conversation context.

  1. Read _CLAUDE.md first if it exists in the vault root
  2. Identify the user's current claim, plan, or assumption - either from the argument or from recent conversation
  3. Extract the key premises behind that position
  4. Search the vault for counter-evidence - spawn parallel subagents:
    • Decisions agent: search Key Decisions sections in project notes for past decisions that contradicted or reversed similar thinking
    • Failures agent: search dev logs, daily notes, and archives for past failures, regrets, or lessons learned related to this topic
    • Contradictions agent: search for notes where the user held the opposite position or flagged risks about this exact approach
  5. Synthesize a structured "Red Team" analysis:
    • Your position: restate the claim clearly
    • Counter-evidence from your vault: cite specific notes, dates, and quotes
    • Blind spots: what the user might be ignoring based on their own history
    • Verdict: is this position consistent with past experience, or does the vault suggest caution?
  6. Log the challenge in today's daily note under a Thinking section
  7. Offer to save the full challenge report as a standalone note in the concepts/ideas folder (resolved per references/folder-map.md), type: challenge, thinking-tool schema in references/ai-first-rules.md

Do not be agreeable. The entire point is to pressure-test. Cite specific vault files. If you find nothing contradictory, say so honestly - but search thoroughly first.


AI-first rule: Every note created or updated by this command MUST follow references/ai-first-rules.md - ## For future agent preamble, rich frontmatter (type, date, tags, ai-first: true, plus type-specific fields), recency markers per external claim, mandatory [[wikilinks]] for every person/project/concept referenced, sources preserved verbatim with URLs inline, and confidence levels where applicable. If that path does not resolve from your working directory, search upward for it; if you still cannot read it, say so before writing rather than producing a note that silently skips the rule. The vault is for future agent retrieval - not human reading.

Anti-fabrication: Search exhaustively before claiming any note, person, or file is absent - false absence is the most common failure mode - and never invent facts, entities, or dates (mark unknowns as TBD). See the anti-fabrication and search-completeness hard rules in references/ai-first-rules.md.

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. 10d ago First seen · 36 lines · 20 tokens per session scan A 277115ffa8c8

Subscribe to this mod's changes

obsidian-challenge is a command published in the GitHub repository eugeniughelbur/obsidian-second-brain (4,376 stars, last pushed 3d ago), licensed MIT. It adds 20 tokens to every session and 772 once invoked, about $0.0001 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 2026-08-30.