Feature request: Interactive tutoring mode for Claude CLI

Preflight Checklist

• [x] I have searched existing requests and this feature hasn't been requested yet
• [x] This is a single feature request (not multiple features)

Problem Statement

Interactive tutoring mode (--tutor) for guided hands-on learning

Description
Claude CLI already monitors files and executes terminal commands in real-time. What's missing is a tutoring mode that leverages this to teach interactively.
What I'm proposing:
A --tutor flag that shifts Claude into instructor mode:

1. Lecture phase — Claude explains a concept or task
2. Practice phase — Student attempts commands or edits files in their terminal/editor
3. Live validation — Claude watches the changes in real-time and:

Confirms if the student got it right
Offers hints if they're stuck
Explains what went wrong without just giving the answer
Guides them back on track

Why this matters

• Hands-on learning without context-switching
• Perfect for infrastructure setup, codebase onboarding, architecture learning
• Leverages existing CLI infrastructure (file monitoring, command execution)
• Differentiates Claude Code from other AI CLI tools

Proposed Solution

Add a --tutor flag to Claude CLI that activates interactive tutoring mode:

Mode behavior

• Claude begins with a lecture/explanation of the current topic or task
• Prompts the user to attempt the hands-on work (run commands, edit files, etc.)
• Monitors the filesystem and terminal output in real-time
• Validates the student's work:

If correct: confirms success, explains what they did right, moves to next step
If incorrect or incomplete: provides hints, asks clarifying questions, guides toward the solution without spoiling it
If stuck: offers graduated help (concept review → example → guided steps)

Technical approach
The CLI already has the infrastructure:

• Real-time file watching (for detecting edits)
• Command execution and output capture (for validating terminal work)
• Full codebase context (for understanding scope)

Tutoring mode is mainly a prompting strategy change: shift from "execute this task" to "guide the student through learning this task" while using the same monitoring and execution capabilities.

Alternative Solutions

Priority

Low - Nice to have

Feature Category

CLI commands and flags

Use Case Example

I'm currently using Claude CLI to set up an Apache webserver with SSH access to my repos (aiming for https://www.yourwebsite.local). The CLI has been invaluable — it explains the difference between Nginx and Apache, walks me through MariaDB installation, clarifies SSL certificate setup, etc.
A tutoring mode would make this seamless: Claude lectures on each concept, I try the commands, it validates my setup in real-time and corrects me before I move forward. Right now I'm context-switching between Claude and terminal; tutoring mode would merge them.

<img width="1907" height="1076" alt="Image" src="https://github.com/user-attachments/assets/d852344d-bfa1-497d-bcc6-fa6caec655f2" />

<img width="1907" height="1076" alt="Image" src="https://github.com/user-attachments/assets/464404ee-5c7a-487f-b1bc-0ddc36aa2b00" />
<img width="1907" height="1076" alt="Image" src="https://github.com/user-attachments/assets/baa05844-2503-440a-be27-3799cce27499" />

Additional Context

_No response_