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Troubleshooting

Common issues and their solutions.

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.

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.

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

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.

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

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

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.

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.

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:

Windows-specific issues

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

Cursor-specific issues

See docs/cursor.md for Cursor IDE troubleshooting.

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