If you bring up a help page by pressing F1, doing a search, filtering via the Index, or any other method that doesn’t involve the Contents tool window, you’ll notice the Contents window will be out of sync with the current page.

This blog post has moved to http://saraford.net/2008/12/09/did-you-know-how-to-sync-your-current-help-page-with-the-contents-tree-even-if-the-option-isnt-available-374/