Hi Mike

When Word creates a table of contents, it can't "see" anything in the
drawing layer. It can only "see" what's in the text layer. So if you have
captions that are text, they will be picked up in the Table of Contents. But
if some of the captions are in a text box, the TOC can't see them.

There are only two ways to have a caption appear in a Table of Contents: put
the caption as straight text, or put it in a frame.

For information about how to work with pictures and captions in frames see
How to keep a figure on the same page as its caption
http://www.ShaunaKelly.com/word/figures/keepwithcaption.html

Hope this helps.

Shauna Kelly.  Microsoft MVP.
http://www.shaunakelly.com/word