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Can you tell us what output you are producing as the answer depends on that.
The output format is Microsoft HTML Help
If your output is .CHM, is your TOC Binary? If so, any change to the icons won't be reflected in the help file. To toggle Binary, right-click your Microsoft HTML Help layout in the Single Source Layouts pseudo folder and choose Properties. Then click the Edit (Version 7) or Advanced (Version 6) button. Now click the TOC Styles tab. There is a check box that governs the setting. To specify the different images, you need to ensure the TOC isn't Binary. Acutally, assuming you are creating .CHM output and the current setting is Binary, you should see that most of the other check boxes are in a disabled state until you DE-select Binary.
If your output is WebHelp, that number will have no influence. For WebHelp, it depends on whether you are using a skin as well as the image supplied.
The Binary checkbox is not checked.
In re-reading your initial post, it would seem that you think changing the icon in one single place will configure the default used for all pages in the TOC. There is no way to accomplish this I'm aware of. You have to individually choose different icons for each page if you want them all to be different.
There is a way to use a bitmap image called an "icon strip". But that carries with it enough overhead to make it unattractive to 99% of .CHM developers. You have to ensure it's copied to each PC along with the .CHM, futz with pathing, etc.