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Salesforce does not guarantee all file types and their contained features will properly generate previews in Content. Please refer this doc detailing the limitations of Content file previews. Limitation around PDF files Large numbers of pages. Exact number is dependent on their content but if the count is high (100+) it may cause the preview generation ...


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UPDATE: the ContentDocumentLink wasn't required as there was something in play that already linked the content version to the object.


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N.B. ContentWorkSpace is the SObject used for Libraries One solution to this is to give the user CRM Content User permission on their User record.


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I created a rollup with DLRS using the ContentDocumentLink object as David Reed recommended above, and it worked perfectly. I then was able to create a normal validation rule requiring the rollup was greater than 0.


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There is no direct way of doing this currently, There is an idea open for the same.


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