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Headings, Styles, and Table of Contents (TOC)

New Era Systems, LLC Updated January 2026

A Word document feels “right” when headings are consistent. md2docx maps Markdown headings directly to Word’s Heading styles, which enables clean formatting and an optional table of contents.

The goal is simple: write Markdown that has a clear structure, then let Word do what it’s good at: navigation, page layout, and review workflows (comments, tracked changes, and approvals).

Why headings matter in Word

In Word, headings are not just “big bold text”. They’re semantic markers that power features people actually use in long documents:

  • Navigation Pane for jumping between sections during review.
  • Table of Contents that stays in sync as the document evolves.
  • Consistent spacing and typography when you apply a template.
  • Outline view for reorganizing sections without copy/paste chaos.

If you keep your structure as headings (instead of bold paragraphs or numbered lists), the final DOCX becomes much easier for stakeholders to scan and comment on.

Use a predictable heading hierarchy

In Markdown:

# Title (Heading 1)

## Section (Heading 2)

### Subsection (Heading 3)

#### Detail (Heading 4)
  • Use exactly one # title per document when possible.
  • Don’t skip levels (avoid jumping from # straight to ###).
  • Keep headings short and descriptive; they become navigation inside Word.

Think of # as the document’s “chapter” level and ## as your main sections. Most business docs rarely need #### or deeper headings.

A report outline you can reuse

If you want a structure that consistently converts well to Word, start from a repeatable outline. Here’s a practical skeleton you can paste into ChatGPT/Claude/Gemini (or your own editor) and fill in: 

# Project Title

## Executive summary

## Background

## Goals and non-goals

## Proposed approach

## Implementation plan

## Risks and mitigations

## Appendix

This gives reviewers a predictable flow, makes your TOC useful, and keeps conversion output consistent even when content comes from multiple authors.

Enable a Word Table of Contents

On the Convert page, enable the “Insert table of contents” option. md2docx will insert a Word TOC based on your headings.

TOCs work best when Heading 1–3 represent the structure you want a reader to scan (Title → Sections → Subsections).

Update the TOC after conversion

Many Word viewers will show the TOC immediately, but Word may prompt you to update fields when you open the file (especially if headings changed). If your TOC doesn’t look right:

  1. Open the DOCX in Microsoft Word (desktop if possible).
  2. Right-click inside the Table of Contents.
  3. Choose Update Field → Update entire table.

Pagination tips

  • If you want each top-level section to begin on a new page, enable “Page break before H1”.
  • Use horizontal rules (---) to force page breaks (or section breaks) when needed. This is useful for appendices, wide tables, or changing orientation.

A good pattern for longer reports is: enable Page break before each H1, then use horizontal rules to separate major parts (for example, main report vs appendix).

For a complete breakdown of layout options, see Advanced conversion options.

Heading numbering: do it in Word (or your template)

If your organization prefers numbered headings (for example “1. Introduction”, “1.1 Scope”), it’s usually better to configure numbering in Word rather than typing numbers into your Markdown headings.

  • Numbers typed into headings can become inconsistent when sections move.
  • Word’s multilevel list numbering can update automatically when you reorder content.
  • A template can enforce the same numbering rules across many documents.

Start with a template that defines heading styles and numbering rules (see Custom DOCX templates).

Template reminder

Your template controls how headings look. If headings are “unstyled” or inconsistent, upload a template that defines Heading 1–6 (see Custom templates).

Common mistakes (and how to fix them)

Skipping heading levels

Jumping from # to ### looks okay in a Markdown preview, but it creates weird structure in Word. Use ## for main sections, then ### only when you truly need subsections.

Using bold text as a “heading”

A bold line is not a heading in Word. If you want it in the TOC and navigation, make it a real Markdown heading.

Too many H1s

Multiple # headings can work, but in business docs it often makes the TOC look odd. Prefer a single title as H1, and use H2 for the rest of the structure.

Pre-conversion checklist

  • One clear title (#) and consistent H2/H3 structure.
  • No skipped heading levels.
  • TOC enabled if the document is longer than 2–3 pages.
  • Page/section break rules chosen intentionally (not as a last-minute hack).
  • Template uploaded (or selected) if you care about branding and spacing.

Ready to test? Convert a small outline first on /convert, then reuse that structure for your longer docs.