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[GH-ISSUE #31] No matter how complex the tasks I assign to it, the skill are never triggered. #22

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opened 2026-03-03 18:50:03 +03:00 by kerem · 4 comments

kerem commented

2026-03-03 18:50:03 +03:00

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Originally created by @JianweiWangs on GitHub (Jan 16, 2026).
Original GitHub issue: https://github.com/OthmanAdi/planning-with-files/issues/31

Please, I’d like to understand what I should do to make this work.

Originally created by @JianweiWangs on GitHub (Jan 16, 2026). Original GitHub issue: https://github.com/OthmanAdi/planning-with-files/issues/31 <img width="1248" height="1128" alt="Image" src="https://github.com/user-attachments/assets/5324e440-273e-40ca-a83c-b505e25e8171" /> Please, I’d like to understand what I should do to make this work.

kerem closed this issue

2026-03-03 18:50:03 +03:00

kerem commented

2026-03-03 18:50:04 +03:00

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@OthmanAdi commented on GitHub (Jan 17, 2026):

Hi @JianweiWangs,

Thank you for your question, and apologies for my delayed response! I understand your frustration – you want the skill to activate automatically for complex tasks, but it's not triggering.

Let me explain what's happening and give you some proven solutions.

Why Skills Don't Always Auto-Activate

Claude Code uses progressive disclosure – it scans skill descriptions and only loads them when it thinks they're needed. The decision is based on:

Your request matching trigger words in the skill description
Claude's assessment of task complexity
Other skills that might have higher priority

Unfortunately, Claude's autonomous activation isn't always reliable, even for complex tasks. This is a known limitation of Claude Code's skill system, not something wrong with your setup!

✅ Proven Solutions

Solution 1: Manual Invocation (Most Reliable)

Simply use the slash command:

/planning-with-files

Then describe your complex task. The skill is marked as user-invocable: true specifically for this purpose. This works 100% of the time.

Solution 2: Use Trigger Phrases

Include these phrases in your requests to improve auto-activation:

"Create a task plan for..."
"This is a multi-step project"
"I need planning for this complex task"
"Help me plan and build..."
"Multi-phase implementation..."

Example:
Instead of: "Build a user authentication system"
Try: "Create a task plan to build a user authentication system with planning files"

Solution 3: Be Explicit About Complexity

Mention the number of steps or tools needed:

"This will require multiple steps"
"This is a research project"
"We'll need to create several files"
"This involves 5+ different operations"

Solution 4: Session Start Reminder

While the SessionStart hook doesn't work in skills (due to progressive loading), you can create a user-level hook to remind yourself.

Add to ~/.claude/hooks.json:

{
  "hooks": {
    "SessionStart": [
      {
        "type": "command",
        "command": "echo '💡 Reminder: Use /planning-with-files for complex multi-step tasks'"
      }
    ]
  }
}

Real Example That Works

Here's a request format that consistently triggers the skill:

"I need help with a complex multi-step project. Create a task plan to build a REST API with authentication, database integration, and testing. This will require planning across multiple files."

The keywords here:

✅ "complex"
✅ "multi-step"
✅ "task plan"
✅ "planning"
✅ Multiple components mentioned

Understanding the Limitation

The truth is: Claude Code's autonomous skill activation is imperfect by design. Even with perfect descriptions, it won't activate 100% of the time. This is why the skill is user-invocable – manual invocation via /planning-with-files is actually the intended primary usage method.

Think of auto-activation as a bonus feature that sometimes works, not the main way to use it.

My Recommendation

Best Practice:

For ANY complex task (3+ steps), start with /planning-with-files
Describe your task after the skill loads
Let Claude create the planning files
Work through your task with proper tracking

This gives you 100% reliability instead of hoping for auto-activation.

Bottom line: The skill works perfectly when invoked manually. Auto-activation is unreliable across ALL Claude Code skills, not just this one. Use /planning-with-files and you'll have a great experience!

Does this help? Let me know if you need any clarification or if you encounter issues after manually invoking the skill.

Best regards,
Ahmad

@OthmanAdi commented on GitHub (Jan 17, 2026): Hi @JianweiWangs, Thank you for your question, and apologies for my delayed response! I understand your frustration – you want the skill to activate automatically for complex tasks, but it's not triggering. Let me explain what's happening and give you some proven solutions. ## Why Skills Don't Always Auto-Activate Claude Code uses **progressive disclosure** – it scans skill descriptions and only loads them when it thinks they're needed. The decision is based on: 1. Your request matching trigger words in the skill description 2. Claude's assessment of task complexity 3. Other skills that might have higher priority Unfortunately, Claude's autonomous activation isn't always reliable, even for complex tasks. This is a known limitation of Claude Code's skill system, not something wrong with your setup! ## ✅ Proven Solutions ### Solution 1: Manual Invocation (Most Reliable) Simply use the slash command: ``` /planning-with-files ``` Then describe your complex task. The skill is marked as `user-invocable: true` specifically for this purpose. This works 100% of the time. ### Solution 2: Use Trigger Phrases Include these phrases in your requests to improve auto-activation: - "Create a task plan for..." - "This is a multi-step project" - "I need planning for this complex task" - "Help me plan and build..." - "Multi-phase implementation..." **Example:** Instead of: *"Build a user authentication system"* Try: *"Create a task plan to build a user authentication system with planning files"* ### Solution 3: Be Explicit About Complexity Mention the number of steps or tools needed: - "This will require multiple steps" - "This is a research project" - "We'll need to create several files" - "This involves 5+ different operations" ### Solution 4: Session Start Reminder While the SessionStart hook doesn't work in skills (due to progressive loading), you can create a user-level hook to remind yourself. Add to `~/.claude/hooks.json`: ```json { "hooks": { "SessionStart": [ { "type": "command", "command": "echo '💡 Reminder: Use /planning-with-files for complex multi-step tasks'" } ] } } ``` ## Real Example That Works Here's a request format that consistently triggers the skill: > *"I need help with a complex multi-step project. Create a task plan to build a REST API with authentication, database integration, and testing. This will require planning across multiple files."* The keywords here: - ✅ "complex" - ✅ "multi-step" - ✅ "task plan" - ✅ "planning" - ✅ Multiple components mentioned ## Understanding the Limitation The truth is: **Claude Code's autonomous skill activation is imperfect by design**. Even with perfect descriptions, it won't activate 100% of the time. This is why the skill is `user-invocable` – manual invocation via `/planning-with-files` is actually the *intended* primary usage method. Think of auto-activation as a bonus feature that sometimes works, not the main way to use it. ## My Recommendation **Best Practice:** 1. For ANY complex task (3+ steps), start with `/planning-with-files` 2. Describe your task after the skill loads 3. Let Claude create the planning files 4. Work through your task with proper tracking This gives you 100% reliability instead of hoping for auto-activation. --- **Bottom line:** The skill works perfectly when invoked manually. Auto-activation is unreliable across ALL Claude Code skills, not just this one. Use `/planning-with-files` and you'll have a great experience! Does this help? Let me know if you need any clarification or if you encounter issues after manually invoking the skill. Best regards, Ahmad

kerem commented

2026-03-03 18:50:04 +03:00

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@dalisoft commented on GitHub (Jan 19, 2026):

Myabe related #39

@dalisoft commented on GitHub (Jan 19, 2026): Myabe related #39

kerem commented

2026-03-03 18:50:04 +03:00

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@JianweiWangs commented on GitHub (Jan 19, 2026):

Hi,@OthmanAdi Sorry for my late reply, and thank you very much for your clear and patient answer. I will try out your suggestion right away.

@JianweiWangs commented on GitHub (Jan 19, 2026): Hi,@OthmanAdi Sorry for my late reply, and thank you very much for your clear and patient answer. I will try out your suggestion right away.

kerem commented

2026-03-03 18:50:04 +03:00

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@OthmanAdi commented on GitHub (Jan 20, 2026):

@JianweiWangs hey buddy! i think we fixed it please check out the latest release and this dicussion #39

@OthmanAdi commented on GitHub (Jan 20, 2026): @JianweiWangs hey buddy! i think we fixed it please check out the latest release and this dicussion #39

kerem referenced this issue

2026-03-03 18:50:19 +03:00

[GH-ISSUE #93] Error: Failed to install: ENOENT: no such file or directory #55

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