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The Quick launch section of a MOSS wiki site only shows the initial Page under wiki pages. I have to manually add the wiki pages that I create to the naviagtion in order to see them under the quick launch. Is there a way to automate this?

Also the 'show pages' option is inactive (unable to select) under Naviagtion settings of a MOSS wiki site. Is there a way to enable this?

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There isn't anyway to do this out of the box. The Show Pages option is only for SharePoint pages in a page library. Wiki pages would either need to be added manually or you could write a custom event receiver on the wiki library that adds to the quick launch from code.

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