[CLI] Skills do not auto-trigger via natural language (works in GUI)

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1

Where does the bug appear (feature/product)?

  • [ ] Cursor IDE

  • [x] Cursor CLI

Describe the Bug Custom skills do not trigger via natural language keywords in the CLI, even when “When to Use” instructions are explicitly defined. The exact same skill and prompt work perfectly in the Cursor GUI. In the CLI, the agent ignores the intent unless I manually invoke the skill using the slash command (e.g., /$create-jira-task).

Steps to Reproduce

  1. Create a custom skill (e.g., create-jira-task) with a .md file.

  2. Add a ## When to Use section with natural language triggers (e.g., “Use this skill when the user says ‘create task’”).

  3. Open the Cursor CLI.

  4. Type a trigger phrase like “Let’s open a Jira ticket.”

  5. Observe that the agent does not trigger the tool and responds generically.

Expected Behavior The CLI agent should parse the “When to Use” instructions and automatically trigger the skill when the user types a relevant phrase, matching the behavior of the GUI agent.

Screenshots / Screen Recordings

CLI:

Screenshot 2026-01-29 at 12.07.52
Screenshot 2026-01-29 at 12.07.521271×221 101 KB

GUI:

Screenshot 2026-01-29 at 12.09.14
Screenshot 2026-01-29 at 12.09.14398×263 12.9 KB

Operating System

  • [x] MacOS

IDE: 2.4.22 (Universal) VSCode Version: 1.105.1 CLI: CLI Version 2026.01.28-fd13201

Additional Information For context, here is the specific configuration I am using that works in the GUI but fails in the CLI:

Markdown

## When to Use

- Use this skill when the user wants to create a Jira task or ticket
- Use this skill when the user says "create task", "new ticket", or "open a Jira"
- This skill is helpful for structuring tasks with proper titles, descriptions, and epic linking
2

Hi there!

We detected that this may be a bug report, so we’ve moved your post to the Bug Reports category.

To help us investigate and fix this faster, could you edit your original post to include the details from the template below?

Bug Report Template - Click to expand

Where does the bug appear (feature/product)?

  • Cursor IDE
  • Cursor CLI
  • Background Agent (GitHub, Slack, Web, Linear)
  • BugBot
  • Somewhere else…

Describe the Bug
A clear and concise description of what the bug is.

Steps to Reproduce
How can you reproduce this bug? We have a much better chance at fixing issues if we can reproduce them!

  1. …
  2. …
  3. …

Expected Behavior
What is meant to happen here that isn’t working correctly?

Screenshots / Screen Recordings
If applicable, attach images or videos (.jpg, .png, .gif, .mp4, .mov)

Operating System

  • Windows 10/11
  • MacOS
  • Linux

Version Information

  • For Cursor IDE: Menu → About Cursor → Copy
  • For Cursor CLI: Run agent about in your terminal
IDE:
Version: 2.xx.x
VSCode Version: 1.105.1
Commit: ......

CLI:
CLI Version 2026.01.17-d239e66

For AI issues: which model did you use?
Model name (e.g., Sonnet 4, Tab…)

For AI issues: add Request ID with privacy disabled
Request ID: f9a7046a-279b-47e5-ab48-6e8dc12daba1
For Background Agent issues, also post the ID: bc-…

Additional Information
Add any other context about the problem here.

Does this stop you from using Cursor?

  • Yes - Cursor is unusable
  • Sometimes - I can sometimes use Cursor
  • No - Cursor works, but with this issue

The more details you provide, the easier it is for us to reproduce and fix the issue. Thanks!

1 Like
4

Hey, thanks for the report. I can see the screenshots. It works fine in the GUI, but the CLI is ignoring the “When to Use” triggers.

You set everything up correctly according to the official docs. The “When to Use” section is meant for exactly this. Skills support in the CLI was added just last week, and it looks like automatic context detection still isn’t working. The only workaround for now is to trigger it manually with /create-jira-task.

I’ll pass this to the team to fix.

1 Like