I love Apple Pages. It’s a clean, fairly minimal word processor. Compared to Microsoft Word, it has approximately 10,000 less buttons.

It has a few shortcomings however, and if you’ve ever tried to take a .pages document, export it to .doc, and then upload it to Kindle Direct Publishing, you may have found that you couldn’t generate the table of contents that Amazon wants. Namely, they want a list of chapters, and those chapters should be enabled as hyperlinks. Apple Pages can’t do this automatically, and neither can Microsoft Word on the Mac.

However, it is possible to do manually with Apple Pages. It takes about ten minutes. Here’s how to generate a Kindle table of contents or TOC on the Mac, using Apple Pages:

  1. Go through your document, and for each chapter title, select the text, and then click Insert -> Bookmark. After you do this the first time, a small link popup window will appear. This is the Inspector, on the “Link” tab. Keep this open. You can click the + button on that window to add subsequent bookmarks once you have the chapter title selected.
  2. Create a new page near the front of the book. Put “Table of Contents” at the top. Then manually type the chapter names, one per line. My chapters are unnamed, so I merely have “Chapter 1”, “Chapter 2”, etc.
  3. While we’re making bookmarks, let’s also generate the two Amazon required bookmarks:
    1. Select “Table of Contents”, and click Insert -> Bookmark, and name it “TOC”. All uppercase, just those three letters. (You can double-click the bookmark names in the popup window to rename them.)
    2. Go to the first page of your book – the actual start of text. Place the cursor before the first character of text. Again click Insert -> Bookmark, and name it “Start”.
  4. Go to the Inspector window, and click the hyperlink tab instead of the bookmark tab.
  5. For each chapter title in your manually created table of contents
    1. select the text. 
    2. In the Inspector, check the Enable As Hyperlink. 
    3. In the Link To: dropdown, select Bookmark. 
    4. In the Name field, select the name of the bookmark – your chapter title.
Note: if the small link window closes, you can get back to it by clicking View -> View Inspector, and then clicking the second to last icon that looks like a arrow. 
When you’re done, of course, you’ll want to export your Pages document as Word, and then you can upload to Kindle Direct, and it will convert it into a Kindle ebook with a valid table of contents, with the required Start and TOC bookmarks that Kindle insists on.