How to convert TXT to MOBI with table of contents using Calibre

· 2 min readTutorialSoftware & Apps#calibre#conversion#kindle#tutorial

A plain .txt file dropped onto a Kindle becomes a wall of text with no chapters, no navigation, and no formatting. Calibre fixes all of that. Here’s how to turn any TXT into a properly structured MOBI ebook with a working table of contents.

Step 1: Prepare your TXT file

Calibre detects chapters using pattern matching. Before you import the file, add markers so Calibre knows where each chapter begins. The simplest approach:

Chapter 1
The first paragraph of your book...

Chapter 2
The second chapter begins...

Calibre’s TXT input parser has a built-in “Detect chapters” option. When enabled, it looks for lines matching patterns like Chapter 1, CHAPTER ONE, or numbered headings. Mark your chapters clearly and Calibre handles the rest.

For more complex structures — prologues, epilogues, parts — you’ll want to use Markdown format instead of plain TXT. Markdown gives you explicit heading levels (# Part One, ## Chapter 1) that Calibre converts directly to EPUB/MOBI navigation.

Step 2: Import and configure

  1. Open Calibre, click Add Books, select your TXT file

  2. Select the book, click Convert Books → Convert Individually

  3. In the conversion dialog, set Output format to MOBI

  4. Go to the TXT Input tab:

    • Paragraph style: Auto (or “Block” if your TXT has blank lines between paragraphs)
    • Formatting style: Auto
    • Check Detect chapters

  5. Go to the Table of Contents tab:

    • Under “Level 1 TOC,” click the magic wand icon
    • Your detected chapters should appear in the list
    • Confirm the structure looks correct

  6. Go to the MOBI Output tab:

    • Check Put generated Table of Contents at start of book

Step 3: Add a cover

No one wants a generic Calibre cover. In the main Calibre window:

  1. Right-click the book → Edit metadata → Edit metadata individually
  2. Click the brown book icon next to the cover area
  3. Select an image file (JPEG or PNG, at least 600×800 pixels)
  4. Click OK

The cover gets embedded during conversion. If you already converted the book, you’ll need to convert again for the new cover to appear.

Step 4: Convert and test

Click OK to start conversion. For a typical 400-page novel, this takes about 5-10 seconds.

Connect your Kindle via USB, right-click the book, and select Send to Device → Send to main memory. Eject your Kindle and check the result: the book should open with a table of contents at the front, and the Go To menu should list each chapter.

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