Markdown Table of Contents Generator

A universal TOC generator that works with any markdown file. Supports batch processing, configurable header levels, and smart insertion.

Quick Start

# Single file
python "${CLAUDE_PLUGIN_ROOT}/scripts/generate_toc.py" README.md

# Preview without changes
python "${CLAUDE_PLUGIN_ROOT}/scripts/generate_toc.py" --dry-run README.md

# All markdown files in docs/
python "${CLAUDE_PLUGIN_ROOT}/scripts/generate_toc.py" docs/*.md

# Recursive processing
python "${CLAUDE_PLUGIN_ROOT}/scripts/generate_toc.py" --recursive .

Note: You can also copy the script to your project and run it locally.

Options

| Option | Default | Description | |--------|---------|-------------| | --dry-run | false | Preview TOC without modifying files | | --min-level N | 2 | Minimum header level (1-6) | | --max-level N | 3 | Maximum header level (1-6) | | --title TEXT | "Table of Contents" | Custom TOC title | | --no-title | false | Omit TOC title | | --recursive, -r | false | Process .md files recursively | | --insert MODE | auto | Insertion mode: auto, top, marker | | --marker TEXT | <!-- TOC --> | Custom marker for marker mode |

Insertion Modes

Auto Mode (default)

Smart detection in this order:

1. Replace existing ## Table of Contents section
2. Insert after first --- separator (common README pattern)
3. Insert after YAML frontmatter
4. Insert after first header
5. Insert at top of file

python scripts/generate_toc.py README.md

Top Mode

Insert at top of file, respecting YAML frontmatter:

python scripts/generate_toc.py --insert top README.md

Marker Mode

Insert/replace between marker pairs:

python scripts/generate_toc.py --insert marker README.md

In your markdown file:

<!-- TOC -->
(TOC will be inserted/updated here)
<!-- /TOC -->

Custom markers:

python scripts/generate_toc.py --insert marker --marker "<!-- INDEX -->" README.md

Header Level Control

Include only H2-H3 (default):

python scripts/generate_toc.py README.md

Include H1-H4:

python scripts/generate_toc.py --min-level 1 --max-level 4 README.md

Include only H2:

python scripts/generate_toc.py --min-level 2 --max-level 2 README.md

Batch Processing

Glob Patterns

# All .md in current directory
python scripts/generate_toc.py *.md

# All .md in docs/
python scripts/generate_toc.py docs/*.md

# Specific pattern
python scripts/generate_toc.py docs/guide-*.md

Recursive

# All .md files recursively
python scripts/generate_toc.py --recursive .

# Recursive in specific directory
python scripts/generate_toc.py --recursive docs/

Multiple Paths

python scripts/generate_toc.py README.md CONTRIBUTING.md docs/

Output Examples

With Title (default)

## Table of Contents

- [Installation](#installation)
- [Usage](#usage)
  - [Basic Usage](#basic-usage)
  - [Advanced Usage](#advanced-usage)
- [Contributing](#contributing)

Without Title

python scripts/generate_toc.py --no-title README.md

- [Installation](#installation)
- [Usage](#usage)
  - [Basic Usage](#basic-usage)

Custom Title

python scripts/generate_toc.py --title "Contents" README.md

## Contents

- [Installation](#installation)

Anchor Generation

GitHub-compatible anchors:

• Lowercase conversion
• Spaces to hyphens
• Special characters removed
• Markdown formatting stripped (**bold**, `code`)
• Emoji removed
• Multiple hyphens collapsed

| Header | Anchor | |--------|--------| | ## Getting Started | #getting-started | | ## **Bold** Header | #bold-header | | ## Header with code`` | #header-with-code | | ## Header #1 | #header-1 |

Skipped Content

The script automatically skips:

• YAML frontmatter (between --- markers)
• Code blocks (``` or ~~~)
• Existing "Table of Contents" headers
• Headers outside configured level range

Dry Run Preview

Always preview first with --dry-run:

python scripts/generate_toc.py --dry-run README.md

Output:

[INFO] Found 1 markdown file(s)

============================================================
File: README.md
============================================================
## Table of Contents

- [Installation](#installation)
- [Usage](#usage)
...

Found 15 headers (levels 2-3)

Common Workflows

Update All Project Documentation

python scripts/generate_toc.py --recursive --dry-run .
# Review output, then:
python scripts/generate_toc.py --recursive .

Standardize TOC Markers

# Add markers to files, then:
python scripts/generate_toc.py --insert marker --recursive docs/

Different Levels for Different Files

# Deep TOC for main README
python scripts/generate_toc.py --max-level 4 README.md

# Shallow TOC for guides
python scripts/generate_toc.py --max-level 2 docs/guides/*.md

Troubleshooting

"No headers found"

File may only have H1 headers. Use --min-level 1.

TOC inserted in wrong place

Use --insert marker with explicit markers for precise control.

Anchors don't work

Check for duplicate headers (GitHub appends -1, -2, etc.).

Portability

This script is fully portable:

• No hardcoded paths or project-specific values
• Works with any markdown file
• Standard Python 3 with no dependencies
• Can be copied to any project