Word for Mac can't generate linked TOCs for Kindle

I've been trying to document the simplest way to create an ebook with a tool that most folks already own. The tool I've chosen, Microsoft Word, is a bloated, impossibly complicated piece of software that for some inexplicable reason, is used by a huge proportion of the populace. Feel free to enlighten me about its virtues in the comments.

Anyways, I want to call your attention to one particularly important failing of Microsoft Word for Macintosh: it will only create linked or active TOCs if the TOC contains page numbers. It's really important to include linked TOCS in ebooks, and particularly in Kindle books since most of Kindle devices don't have device-generated or navigational tables of contents, but it doesn't make sense to include page numbers (since they don't make any sense in a digital landscape).

Note that Microsoft Word for Windows is happy to automatically generate a useful TOC, sans page numbers, for an ebook.



Simply uncheck Show page numbers and then check Use hyperlinks instead of page numbers.

Now look at the corresponding dialog box in the latest version of Word for Macintosh:



You can hide the page numbers, but you can't convert them to hyperlinks, and I assure you, after much testing (and confirmation from @ljndawson), that without page numbers, no page links will be created. The TOC is there, but will take you nowhere in the converted ebook.



It makes Word for Mac a much less powerful tool for creating ebooks. Of course, there are solutions (like manually creating bookmarks for each TOC entry), but it's nothing like a one-button solution (!).

Why should anyone care about how Word creates TOCs? Because Word (.doc or .docx) is the one styled format that can be read and converted automatically into Kindle format (using KDP, Send to Kindle, and by emailing the document to a Kindle device). More on that soon.

Using Amazon's Send to Kindle to transfer ebooks and documents to Kindle

Amazon has just released the Send to Kindle app for Macintosh. It already exists for PCs. This is an app that facilitates getting documents in various formats—Word (.doc and .docx), text (.txt), RTF (.rtf), images (.jpeg, .gif, .png, .bmp) and PDF (.pdf)—to your Kindle.

Once you've downloaded and installed Send to Kindle, you can activate the app in several different ways. First, you can right-click a document in the Finder and choose the Send to Kindle option near the bottom of the menu.



You can choose Send to Kindle from the Printer menu in any program that has one (here's Word):



Finally, you can click the Send to Kindle icon on the dock or drag a document to the Send to Kindle icon directly.



Whichever method you choose, you'll see the Send to Kindle's window in which you can specify a new title for the document and choose which Kindle you want to send the document to. You will also specify whether you want to use free Wifi or incur extra charges by using Amazon's Whispernet service.



If you check "Archive document in your Kindle Library" (which is on by default), your document will be available in the Kindle cloud, and thus to all of your Kindle devices. You can even deselect a device and send your document only to the cloud.

Format

Notice at the bottom of the window that you'll be advised about which format your document will be converted to. If you right-click or drag and drop, Send to Kindle will convert Word, text, and RTF to Kindle format, and preliminary testing seems to indicate that it uses the same KindleGen algorithms that are used by Kindle Previewer and KDP. If you right-click or drag and drop a PDF file, you'll have the option (in the aptly named Options panel) to convert the PDF to Kindle format. I tested some simple documents, and it seemed to work quite well.



If you use the print option, it will always send the document as a PDF, and the PDF cannot be converted to Kindle format. Note that the PDF document will be much larger than the Kindle version.



All in all, the Send to Kindle app looks like a useful tool for getting documents into your Kindle. The Send to Kindle documentation has a few more details.