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Rather than sync data from the document set to its contents, I want the data in the document set’s contents to be synced out to the document set itself. So if a file in the document set has a Customer Name value of “ABC Co”, the document set itself will take on the Customer Name = “ABC Co”.

Any thoughts?

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Just to follow up, I was never able to get syncing to work in the reverse direction, but I did solve my problem – via workflow.

A document that will later go in a document set is created via workflow on SharePoint, so I included in that workflow an extra step to actually create the document set with some of the same info found in the document. It's no true sync, but it's enough for now.

I hope in the future, Microsoft lets SharePoint's shared columns sync bi-directionally.

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