Hi Brock,
You can only ever have one instance of a bookmark in a document.
With your 'IndexThis' bookmark, you would need to modify the code to preserve it and, when adding entries, not to simply overwrite what's already there. All possible but your reference to 'the next row' suggests you're using a table. In that case, you could fairly easily iterate through the table rows (even adding rows as needed) without using selections.
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Would it also be possible to have the code run the whole document automatically as opposed to allowing the user to select sections?
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Yes - it's just a matter for using a For each ... Next loop to work through the Sections.