CLI AI Chat System

A unified session management system for AI CLI tools (Claude, Gemini, Codex) that organizes conversations into structured sessions with context tracking, decision logging, and artifact management.

What It Does

CLI AI Chat System provides a disciplined approach to AI-assisted development:

• Session Organization - Each conversation gets its own folder with artifacts, context, and decision tracking
• Multi-Platform Support - Works seamlessly across Claude, Gemini, and Codex
• Planning Mode - Built-in task tracking for complex multi-phase work
• Session Registry - Central tracking of all sessions with status management
• Checkpoint System - Save progress with AI-generated summaries and decisions

Installation

No installation required! Use npx to run directly.

Initialize All Platforms

# Navigate to your project directory
cd my-project

# Initialize with all platforms (Claude, Gemini, Codex)
npx cli-ai-chat-system init

This sets up:

• .claude/commands/ - Custom slash commands for session management
• .gemini/commands/ - Custom slash commands for Gemini (PowerShell-compatible)
• .codex/commands/ - Custom slash commands for Codex
• _templates/session/ - Template files for new sessions
• .cli-ai-chat/ - Session registry and active session tracking

Initialize Single Platform Only

If you only use one AI platform, install just what you need:

# Claude only
npx cli-ai-chat-system init claude

# Gemini only
npx cli-ai-chat-system init gemini

# Codex only
npx cli-ai-chat-system init codex

Update Existing Project

To update system files to the latest version:

# Navigate to your existing project
cd my-project

# Update all installed platforms
npx cli-ai-chat-system update

# Or update a specific platform
npx cli-ai-chat-system update claude
npx cli-ai-chat-system update gemini
npx cli-ai-chat-system update codex

What gets updated:

• Slash commands (.claude/commands/, .gemini/commands/, .codex/commands/)
• Session templates (_templates/session/)
• System documentation (CLAUDE.md)

What is preserved:

• Your sessions (chats/, unnamed_projects/)
• Session registry (.cli-ai-chat/sessions.json)
• Active session pointer (.cli-ai-chat/active-session.txt)

Requirements

• Node.js >= 14.0.0
• jq - JSON processor for command-line operations
  • Windows: choco install jq
  • Mac/Linux: brew install jq

Using Session Commands

After initialization, use slash commands in your AI chat:

# Start a new session
/new-session [project-name] [session-topic]
# Example: /new-session my-website seo-optimization
# Creates: chats/projects/my-website/2025-03-02-seo-optimization/

# Save progress
/checkpoint

# Resume a previous session
/continue-session

# Start planning mode for complex work
/start-plan [plan-name]

# End the session
/end-session

Session Structure

Each session creates an organized folder structure:

chats/
├── projects/
│   └── [project-name]/
│       └── YYYY-MM-DD-[topic]/
│           ├── artifacts/          # Generated outputs
│           ├── core_files/         # Reference materials
│           ├── core_instructions/  # Rules to follow
│           ├── uploaded_files/     # User-provided inputs
│           ├── planning_mode/      # Multi-phase work tracking
│           │   ├── archive/
│           │   ├── YYYY-MM-DD-name-plan.md
│           │   ├── YYYY-MM-DD-name-todo.md
│           │   └── YYYY-MM-DD-name-done.md
│           ├── context.md          # Session overview
│           ├── messages.md         # Conversation summary
│           └── decisions.md        # Decision tree with rationale
└── unnamed_projects/
    └── YYYY-MM-DD-[topic]/
        └── [same structure]

Available Commands

| Command | Description | |---------|-------------| | /new-session [project-name] [session-topic] | Create a new session in chats/projects/[project-name]/YYYY-MM-DD-[session-topic]/ | | /new-session [session-topic] | Create a session without a project in unnamed_projects/YYYY-MM-DD-[session-topic]/ | | /checkpoint | Save progress with AI-generated summary | | /continue-session | Resume a previous session | | /start-plan [plan-name] | Activate planning mode for complex work | | /end-session | Finalize and close the active session |

Session Lifecycle

┌─────────────────────────────────────────────────────────────┐
│                    /new-session                              │
│                    Creates session folder                    │
│                    Sets status: in-progress                  │
├─────────────────────────────────────────────────────────────┤
│                    Work Session                              │
│                    • Use /checkpoint periodically            │
│                    • Use /start-plan for complex work        │
│                    • Artifacts saved to artifacts/           │
├─────────────────────────────────────────────────────────────┤
│                    /end-session                              │
│                    • Final summary generated                 │
│                    • Status: completed/paused/abandoned      │
│                    • Active pointer cleared                  │
└─────────────────────────────────────────────────────────────┘

Planning Mode

For complex multi-phase work, use /start-plan to create:

• plan.md - Master plan with goals, approach, and phases
• todo.md - Active task list organized by phase
• done.md - Completion log

The AI automatically:

• References the plan before major work
• Updates todo.md as tasks progress
• Moves completed tasks to done.md
• Alerts you if work deviates from the plan

Platform-Specific Notes

Gemini (Windows)

The .gemini/commands/ use PowerShell scripts instead of bash, since Gemini natively supports Windows PowerShell.

Claude & Codex

The .claude/commands/ and .codex/commands/ use bash scripts with jq for JSON operations.

Package Contents

cli-ai-chat-system/
├── bin/
│   └── cli-ai-chat-system.js    # CLI entry point
├── template/
│   ├── .claude/commands/         # Claude slash commands
│   ├── .gemini/commands/         # Gemini slash commands (PowerShell)
│   ├── .codex/commands/          # Codex slash commands
│   ├── _templates/session/       # Session file templates
│   ├── CLAUDE.md                 # System documentation
│   └── README.md                 # User guide
├── package.json
└── README.md

Links

• GitHub: https://github.com/nadeemmuhammedk/cli-ai-chat-system
• npm: https://www.npmjs.com/package/cli-ai-chat-system

Keywords

ai, chat, claude, gemini, codex, chatgpt, session, management, cli, scaffolding, template, ai-development, claude-code, session-tracking, multi-platform

License

ISC