SuperCharged-Claude-Code-Upgrade/skills/planning-with-files/docs/troubleshooting.md

Troubleshooting

Common issues and their solutions.

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Templates not found in cache (after update)

Issue: After updating to a new version, /planning-with-files fails with "template files not found in cache" or similar errors.

Why this happens: Claude Code caches plugin files, and the cache may not refresh properly after an update.

Solutions:

Solution 1: Clean reinstall (Recommended)

/plugin uninstall planning-with-files@planning-with-files
/plugin marketplace add OthmanAdi/planning-with-files
/plugin install planning-with-files@planning-with-files

Solution 2: Clear Claude Code cache

Restart Claude Code completely (close and reopen terminal/IDE).

Solution 3: Manual cache clear

# Find and remove cached plugin
rm -rf ~/.claude/cache/plugins/planning-with-files

Then reinstall the plugin.

Note: This was fixed in v2.1.2 by adding templates at the repo root level.

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Planning files created in wrong directory

Issue: When using /planning-with-files, the files (task_plan.md, findings.md, progress.md) are created in the skill installation directory instead of your project.

Why this happens: When the skill runs as a subagent, it may not inherit your terminal's current working directory.

Solutions:

Solution 1: Specify your project path when invoking

/planning-with-files - I'm working in /path/to/my-project/, create all files there

Solution 2: Add context before invoking

I'm working on the project at /path/to/my-project/

Then run /planning-with-files.

Solution 3: Create a CLAUDE.md in your project root

# Project Context

All planning files (task_plan.md, findings.md, progress.md)
should be created in this directory.

Solution 4: Use the skill directly without subagent

Help me plan this task using the planning-with-files approach.
Create task_plan.md, findings.md, and progress.md here.

Note: This was fixed in v2.0.1. The skill instructions now explicitly specify that planning files should be created in your project directory, not the skill installation folder.

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Files not persisting between sessions

Issue: Planning files seem to disappear or aren't found when resuming work.

Solution: Make sure the files are in your project root, not in a temporary location.

Check with:

ls -la task_plan.md findings.md progress.md

If files are missing, they may have been created in:

• The skill installation folder (~/.claude/skills/planning-with-files/)
• A temporary directory
• A different working directory

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Hooks not triggering

Issue: The PreToolUse hook (which reads task_plan.md before actions) doesn't seem to run.

Solution:

1. Check Claude Code version:

   claude --version
   

   Hooks require Claude Code v2.1.0 or later for full support.

2. Verify skill installation:

   ls ~/.claude/skills/planning-with-files/
   

   or

   ls .claude/plugins/planning-with-files/
   

3. Check that task_plan.md exists: The PreToolUse hook runs cat task_plan.md. If the file doesn't exist, the hook silently succeeds (by design).

4. Check for YAML errors: Run Claude Code with debug mode:

   claude --debug
   

   Look for skill loading errors.

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SessionStart hook not showing message

Issue: The "Ready" message doesn't appear when starting Claude Code.

Solution:

1. SessionStart hooks require Claude Code v2.1.0+
2. The hook only fires once per session
3. If you've already started a session, restart Claude Code

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PostToolUse hook not running

Issue: The reminder message after Write/Edit doesn't appear.

Solution:

1. PostToolUse hooks require Claude Code v2.1.0+
2. The hook only fires after successful Write/Edit operations
3. Check the matcher pattern: it's set to "Write|Edit" only

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Skill not auto-detecting complex tasks

Issue: Claude doesn't automatically use the planning pattern for complex tasks.

Solution:

1. Manually invoke:

   /planning-with-files
   

2. Trigger words: The skill auto-activates based on its description. Try phrases like:

   • "complex multi-step task"
   • "research project"
   • "task requiring many steps"

3. Be explicit:

   This is a complex task that will require >5 tool calls.
   Please use the planning-with-files pattern.
   

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Stop hook blocking completion

Issue: Claude won't stop because the Stop hook says phases aren't complete.

Solution:

1. Check task_plan.md: All phases should have **Status:** complete

2. Manual override: If you need to stop anyway:

   Override the completion check - I want to stop now.
   

3. Fix the status: Update incomplete phases to complete if they're actually done.

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YAML frontmatter errors

Issue: Skill won't load due to YAML errors.

Solution:

1. Check indentation: YAML requires spaces, not tabs
2. Check the first line: Must be exactly --- with no blank lines before it
3. Validate YAML: Use an online YAML validator

Common mistakes:

# WRONG - tabs
hooks:
	PreToolUse:

# CORRECT - spaces
hooks:
  PreToolUse:

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Windows-specific issues

See docs/windows.md for Windows-specific troubleshooting.

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Cursor-specific issues

See docs/cursor.md for Cursor IDE troubleshooting.

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Still stuck?

Open an issue at github.com/OthmanAdi/planning-with-files/issues with:

• Your Claude Code version (claude --version)
• Your operating system
• The command you ran
• What happened vs what you expected
• Any error messages