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How can I re-establish a broken link between a list content type and a Site content type, considering the fact that most of the existing documents are already using the broken list content type?

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Use something like Sharepoint Manager (from CodePlex I believe) to check both content types. If they both have the same IDs then when you update the site content type it should cascade and update any lists using it. Other than that, not much else you can do beside re-creating the list.

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