The issue here seems to have been caused by the captioned items being inserted in-line and the captions being added to the same paragraphs, after which a decision was made to insert a paragraph break and whoever did that didn't take enough care as to how to do that without affecting the bookmarked range.

FWIW, you didn't really need to redo all the captions. All that was required was to fix their ranges, which can be done via Insert|Bookmark, selecting the correct range for each one before updating its bookmark (which you do by telling Word to display hidden bookmarks and, with the correct range selected, simply by clicking 'Add').

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Cheers,
Paul Edstein
[Fmr MS MVP - Word]