You have two choices when faced with the task of numbering headings in a Word document. You can enter the numbers manually and hope nothing changes — lots of luck with that one. Or you can opt for the more efficient solution and create and apply a numbered style. Unfortunately, that can get you into even more trouble, if you don't know what you're doing. To avoid surprises, follow these 10 steps to add a numbering scheme to a style.
Do not let me lead you into a headache under false pretences: this FAQ is not going to tell you how to fix a document that contains broken numbering. It simply explains how the numbering works: this is valuable information if you work with Word a lot, and by understanding it, you can often work out how to fix a document. However, this FAQ is not going to tell you how.  (For a discussion of methods, see: List Restart Methods).
It's also possible to consecutively number list items in InDesign. Create a text frame for your list and click the numbered list button to insert a list. Type your list items, pressing your "Enter" key between items. InDesign consecutively numbers the list automatically; you can change the number it begins with and the style of the numerals. Press your "Alt" key (Windows) or "Option" key (Mac OS) while clicking on the numbered list button to open a dialog where you can modify those options.
It's also possible to consecutively number list items in InDesign. Create a text frame for your list and click the numbered list button to insert a list. Type your list items, pressing your "Enter" key between items. InDesign consecutively numbers the list automatically; you can change the number it begins with and the style of the numerals. Press your "Alt" key (Windows) or "Option" key (Mac OS) while clicking on the numbered list button to open a dialog where you can modify those options.
Another great thing about the Book feature is that it enables you to package all your digital files into one folder—InDesign files, linked images, fonts (if you are using any outside of TypeKit), and your Book file. Chapter 71 in Book Design Made Simple walks you step-by-step through packaging your files for print, and there is only a slight difference when you are working with a Book File: you’ll select all the documents in your Book file rather than just packaging one document.
See Word's Numbering Explained by John McGhie, MVP - comprehensive and not pretty (Downloadable pdf file in letter size) - Reading this is vital to anyone attempting to use automatic numbering or bullets in a law office setting or other places where the documents are likely to be reused or heavily edited. See also How to Create a Template with a downloadable template with style-based numbering.
CK Note: Word 2007 - 2013 interface has an different automatic numbering scheme which I have been told is much less subject to corruption. Microsoft Word 2010 Bible by Herb Tyson, MVP. However numbering is still very imperfect in these later versions. I still recommend following Shauna Kelly's step-by-step instructions (see above) if setting up numbering in a template or in a document likely to be heavily edited. If you start without doing this and end up with "spaghetti numbering," fixing it will be a very large chore!
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