PDFOutline

Take Complete Control of Your PDF Bookmarks and Tables of Contents.

PDFOutline transforms dense, unindexed PDF files into beautifully navigable documents — without the bloat of a full PDF suite. Its Auto Magic feature analyses the font hierarchy of any PDF and automatically generates a structured TOC in seconds. For manual control, drag selected text directly from the PDF view into the outline tree, restructure chapters with drag-and-drop, and batch-rename entries with Find & Replace. Everything runs natively on your Mac, preserving all original formatting and assets.

Screenshots

Key Features

Auto Magic TOC Generation

Analyses the range of fonts used in the PDF and automatically generates a hierarchical table of contents — attempting to tease out heading levels from font size and style without any manual input.

Auto Match from Selected Text

Select any heading text in the PDF viewer and click Auto Match — PDFOutline automatically generates a complete set of outline entries matching that text pattern throughout the document.

Drag Text to Create Outlines

Drag selected text directly from the PDF view and drop it into the TOC list to instantly create a new outline entry linked to that exact page location.

Drag-and-Drop Hierarchical Editing

Drag outlines within the TOC list to reorder, indent, or outdent entries — building nested parent-child structures with shift left, right, up, and down controls for precise level management.

Find & Replace Batch Renaming

Batch-rename outline titles using Find & Replace to remove or substitute unwanted characters. Add prefix, suffix, and number sequence labels to entire batches of outline titles — with case-change controls included.

Copy, Paste & Merge Outlines

Copy and paste selected outlines within a PDF or between PDF documents for reuse. Merge adjacent outlines into one — particularly useful when Auto Magic creates separate entries for multi-line headings.

Undo/Redo & Lossless Saving

Full Undo/Redo support for all outline changes. Saves updated outlines without re-compressing or flattening the document — original colour spaces, fonts, hyperlinks, and searchable text layers are fully preserved.

Built-In PDF Viewer

Full PDF viewing with TOC, thumbnail, and search sidebars — single and double page views, Zoom In/Out/Actual Size, selectable text, and reading history for navigating while editing outlines.

System Requirements

macOS

Version: macOS 10.7 or later

The Word on the Street

Catch up on the latest buzz from our users about PDFOutline

★★★★★

“Works great and is exactly what I was looking for!”

Works great and is exactly what I was looking for! I’m a student and use a lot of large textbook pdfs. Some of the pdfs don’t have a table of contents and it makes jumping around the textbook a time consuming endeavor as I must scroll through hundreds of pages at a time. Preview doesn’t have table of contents editing capabilities, and Adobe’s full software is quite expensive. For $3 dollars I’m able to make tables of contents and save myself…

— Stenway

★★★★★

“Très utile! Very useful!”

J'utilise cette application très souvent pour ajouter une table des matières à des livres et des articles. Elle est très bien conçue, rapide et stable. On peut créer une entrée directement avec une sélection du texte: très efficace! I use this app very often to add a table of content to books and articles. It is very well designed, fast and stable. One can create an outline directly from the text selection: very efficient!

— ljboh

★★★★★

“Works Amazingly”

I had a PDF file with a messed up outline. This was able to create a new outline automatically, and furthermore, I could REARRANGE the pages in the PDF by dragging each chapter around. Really blew my mind.

— Bananaworkout14

★★★★★

“Best tool for TOC”

If you want to edit TOC on macOS, you have no choice but this tool ——we won't think about Adobe, right? :P Fast, lightweight, never damage your text layer, and still work after 4 years.

— appinkie

★★★★★

“Awesome!”

This aprication is very helpful and saving lots of my time! Well working even for long (over 700page) pdf files written in English. If expeting further, recognizing sections as upper class of chapters will be desired,

— MT0002

★★★★★

“Works great and is exactly what I was looking for!”

Works great and is exactly what I was looking for! I’m a student and use a lot of large textbook pdfs. Some of the pdfs don’t have a table of contents and it makes jumping around the textbook a time consuming endeavor as I must scroll through hundreds of pages at a time. Preview doesn’t have table of contents editing capabilities, and Adobe’s full software is quite expensive. For $3 dollars I’m able to make tables of contents and save myself…

— Stenway

★★★★★

“Très utile! Very useful!”

J'utilise cette application très souvent pour ajouter une table des matières à des livres et des articles. Elle est très bien conçue, rapide et stable. On peut créer une entrée directement avec une sélection du texte: très efficace! I use this app very often to add a table of content to books and articles. It is very well designed, fast and stable. One can create an outline directly from the text selection: very efficient!

— ljboh

★★★★★

“Works Amazingly”

I had a PDF file with a messed up outline. This was able to create a new outline automatically, and furthermore, I could REARRANGE the pages in the PDF by dragging each chapter around. Really blew my mind.

— Bananaworkout14

★★★★★

“Best tool for TOC”

If you want to edit TOC on macOS, you have no choice but this tool ——we won't think about Adobe, right? :P Fast, lightweight, never damage your text layer, and still work after 4 years.

— appinkie

★★★★★

“Awesome!”

This aprication is very helpful and saving lots of my time! Well working even for long (over 700page) pdf files written in English. If expeting further, recognizing sections as upper class of chapters will be desired,

— MT0002

★★★★★

“Works great and is exactly what I was looking for!”

Works great and is exactly what I was looking for! I’m a student and use a lot of large textbook pdfs. Some of the pdfs don’t have a table of contents and it makes jumping around the textbook a time consuming endeavor as I must scroll through hundreds of pages at a time. Preview doesn’t have table of contents editing capabilities, and Adobe’s full software is quite expensive. For $3 dollars I’m able to make tables of contents and save myself…

— Stenway

★★★★★

“Très utile! Very useful!”

J'utilise cette application très souvent pour ajouter une table des matières à des livres et des articles. Elle est très bien conçue, rapide et stable. On peut créer une entrée directement avec une sélection du texte: très efficace! I use this app very often to add a table of content to books and articles. It is very well designed, fast and stable. One can create an outline directly from the text selection: very efficient!

— ljboh

★★★★★

“Works Amazingly”

I had a PDF file with a messed up outline. This was able to create a new outline automatically, and furthermore, I could REARRANGE the pages in the PDF by dragging each chapter around. Really blew my mind.

— Bananaworkout14

★★★★★

“Best tool for TOC”

If you want to edit TOC on macOS, you have no choice but this tool ——we won't think about Adobe, right? :P Fast, lightweight, never damage your text layer, and still work after 4 years.

— appinkie

★★★★★

“Awesome!”

This aprication is very helpful and saving lots of my time! Well working even for long (over 700page) pdf files written in English. If expeting further, recognizing sections as upper class of chapters will be desired,

— MT0002

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