Is planning-with-files safe?

https://clawhub.ai/OthmanAdi/planning-with-files

72
CAUTION

This skill implements a sophisticated file-based planning workflow with automatic hooks that fire on nearly every tool call, effectively hijacking the agent's attention and decision-making context. The session-catchup.py script reads previous Claude Code session transcripts from ~/.claude/projects/, creating a cross-session data bridge that exposes prior conversation content. While the skill's intent appears legitimate (Manus-style context engineering for complex tasks), the aggressive hooking pattern, session data access, and behavioral overrides (discouraging built-in TodoWrite) represent meaningful security concerns that warrant careful review before installation.

Category Scores

Prompt Injection 55/100 · 30%
Data Exfiltration 60/100 · 25%
Code Execution 55/100 · 20%
Clone Behavior 95/100 · 10%
Canary Integrity 100/100 · 10%
Behavioral Reasoning 50/100 · 5%

Findings (10)

HIGH Automatic hook-based attention hijacking on every tool call -25

The PreToolUse hook fires on Write, Edit, Bash, Read, Glob, and Grep — nearly every tool the agent uses. Each invocation runs 'cat task_plan.md | head -30', injecting the skill's planning state into the agent's context before every action. This is an intentional attention manipulation technique (documented in reference.md as 'Manipulate Attention Through Recitation') that effectively controls what the agent thinks about before each decision.

HIGH Session transcript reading via session-catchup.py -30

The session-catchup.py script reads Claude Code session files (~/.claude/projects//*.jsonl) which contain full conversation transcripts including user messages, assistant responses, tool inputs/outputs, and potentially sensitive data from prior sessions. It outputs up to 15 messages (user: 300 chars, assistant: 600 chars each) into the current session context. While designed for workflow continuity, this creates a cross-session data bridge that could be weaponized.

HIGH PostToolUse hook injects behavioral directives -10

After every Write or Edit operation, the PostToolUse hook outputs '[planning-with-files] File updated. If this completes a phase, update task_plan.md status.' This is a behavioral directive that steers the agent to update the skill's tracking files after every file modification, regardless of whether the user's task involves the planning workflow.

MEDIUM Automatic script execution on Stop hook -20

The Stop hook automatically runs check-complete.sh every time the agent conversation ends. While the script is benign (only reads task_plan.md and outputs status), the automatic execution pattern means users have shell commands running without per-invocation consent. The Windows path uses '-ExecutionPolicy Bypass' to circumvent PowerShell security.

MEDIUM PowerShell ExecutionPolicy Bypass on Windows -15

The Stop hook explicitly uses 'pwsh -ExecutionPolicy Bypass' and 'powershell -ExecutionPolicy Bypass' to run check-complete.ps1, circumventing Windows PowerShell security policies. While used for a benign script, this pattern normalizes security policy bypass.

MEDIUM Skill overrides built-in agent behavior patterns -10

The skill explicitly instructs the agent not to use TodoWrite ('Don't: Use TodoWrite for persistence → Do: Create task_plan.md file') and replaces it with its own file-based tracking. It also instructs the agent to run its scripts before starting any work, effectively taking over the agent's workflow.

MEDIUM WebFetch and WebSearch in allowed-tools enables potential exfiltration -10

The skill declares WebFetch and WebSearch as allowed tools. While the current skill content doesn't instruct data exfiltration, having these tools available means a modified version could instruct the agent to send session data or file contents to external endpoints.

LOW Cross-skill interference via global hooks -15

The PreToolUse and PostToolUse hooks fire on common tools (Read, Write, Edit, Bash, Glob, Grep) that other skills also use. When multiple skills are installed, this skill's hooks will inject planning context into every other skill's operations, potentially confusing the agent or leaking context between skills.

LOW Reference material provides prompt injection blueprints -10

reference.md documents sophisticated context engineering techniques including KV-cache manipulation, attention hijacking via recitation, and logit masking strategies. While educational, this provides a ready-made blueprint for building more aggressive prompt injection skills.

INFO Clean clone behavior -5

No suspicious activity during clone/install. Only standard Node.js JIT cache files in /tmp/jiti/. No network connections, no unexpected processes, no filesystem changes outside skill directory.