PDF Outline Scissors

A Mac app for editing the bookmarks (outline) of PDF files and extracting pages.

Features

Edit bookmarks: add, rename, delete, indent/outdent, reorder and retarget bookmarks. Undo every step with ⌘Z.
Work with bookmarks in bulk: copy bookmarks from another PDF (with a page offset), edit them as text, shift page numbers, sort by page.
Extract pages: choose where to cut while looking at page thumbnails, and save any page ranges as separate PDFs with their bookmarks. Ranges may overlap.
Your PDF stays intact: saving bookmarks does not change page contents, document information or password protection. Unchanged bookmarks keep their original destinations and colors.

Extracting pages

Choosing where to cut

Click between pages: scissors appear between pages. Click to cut there; click again to remove the cut.
C key (Cut Here): makes one file from the page after the previous cut up to the current page. Pressing it in the middle of an existing file splits that file in two.
Select a range and press A: Shift-click (or Shift+arrow keys) to select pages, then press A to add them as one file. It may overlap other files.
From bookmarks: right-click a bookmark to add its section to the extraction list or to cut just before it. In the Extract menu, "Create from Bookmarks" splits by level 1–3 headings at once.
Add the Rest (Extract menu): adds the pages after the last cut up to the last page as one file.

Each range becomes a row in the extraction list on the right. Unchecked rows are not extracted. Choose Extract (⌘R) in the Extract menu to save the files.

Writing page ranges

You can also type into the Pages column of the extraction list.

10-25 … pages 10 to 25
8 … page 8 only
1-3,8,20- … pages 1 to 3, 8, and 20 to the end (in one file)
20- … page 20 to the end
-5 … pages 1 to 5

Pages are placed in the order you write them: 5-6,1-2 gives pages 5, 6, 1, 2.
If ranges overlap within one row, those pages appear twice.

File names

Files are named "number_heading" automatically, using the heading at the first page of the range (or the heading before it). Without bookmarks, the name is "number_original name_p range".
Edit the name in the File name column; click ↺ to go back to the automatic name.
Write "chapter/01_intro" to save into a subfolder.

Writing the extraction list as text

The extraction list is saved automatically in the .shiori file next to your PDF. It is plain text, so you can also create or edit it in a text editor.

[cuts]

1-6 01_intro

7-12,20 02_basics

# 13-19 03_results

One line makes one file. Separate the page range and the file name with a TAB (or, if there is no TAB, the first space).
Lines starting with "#" are not extracted.
If the file name is empty, the file is named "original name_p1-6.pdf".
If any line has an error, nothing is written and all lines with errors are reported.

Bookmarks in extracted PDFs

Bookmarks within the range are kept. Headings above them that start outside the range (such as chapter titles) are added too. To turn this off, uncheck "When extracting, include parent bookmarks outside the range" in Settings.

Free and Pro

The free version can:

Open, view and edit bookmarks of PDFs up to 100 pages
Save, export and extract PDFs up to 20 pages

Pro adds:

Opening, viewing and editing PDFs of 101 pages or more
Saving, exporting and extracting PDFs of 21 pages or more (including copying bookmarks)
Using the command-line version without limits

Pro is a one-time purchase ($4.99). It is tied to your Apple Account; use "Restore Purchases" on other Macs signed in to the same account.

FAQ

A file named "….shiori" appeared next to my PDF.
It stores your extraction list and the bookmarks you are editing. The app reads it automatically when you open the PDF. Deleting it does not affect the PDF, but the extraction list will be lost. It is plain text, so you can also edit it in a text editor.

My bookmark changes were not saved to the PDF.
In the free version, bookmarks of PDFs with 21 pages or more are kept in the .shiori file instead of the PDF. With Pro, they are saved to the PDF.

Some PDFs cannot be saved or extracted.
If the author of a PDF prohibits changes or assembly (page operations and creating bookmarks), those operations are not available. The reason is shown at the top of the window.

Can I use password-protected PDFs?
Yes. The app asks for the password when opening. Saving bookmarks keeps the original protection. Extracted PDFs are not password-protected.

How do I go back to earlier bookmarks?
Choose File > Revert To to return to a previously saved version.

Where is "Restore Purchases"?
In the PDF Outline Scissors menu > Restore Purchases.

Command-line version

The app includes a command-line tool, shioribasami. To use it:

Choose PDF Outline Scissors > Install Command-Line Tool…. Two command lines are copied.
Paste them into Terminal and press Return (you will be asked for your Mac login password).

The copied lines look like this. If you move the app, do this again.

sudo mkdir -p /usr/local/bin

sudo ln -sf "/Applications/PDFしおりばさみ.app/Contents/SharedSupport/bin/shioribasami" /usr/local/bin/shioribasami

Run shioribasami --help for usage. Page ranges and the extraction list format are the same as in the app.

shioribasami extract lecture.pdf 10-25 # extract pages 10 to 25

shioribasami plan lecture.pdf -l 2 # write an extraction list split by level-2 bookmarks to lecture.shiori

shioribasami split lecture.shiori # extract as listed in the extraction list

The command-line version has the same limits as the app (viewing PDFs up to 100 pages; exporting and extracting PDFs up to 20 pages). With Pro, the command-line version has no limits too. After purchasing, open the app once.

Contact

Please send questions and bug reports by email.

support@mac3.tv

For bug reports, please include your macOS version and the app version (shown in PDF Outline Scissors > About PDF Outline Scissors). It may take a few days to reply.

Requirements

macOS 14 or later (Apple silicon and Intel)

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