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Is it possible to create a workflow that will prompt users to edit a field before allowing them to check in a document? We have a client that can't get end users to change the document status in a column that is a look up column that points to 18 different document statuses. They want end users to change the document status before checking the document in. Currently required check out and version history are turned on. We have SP2016 on premise.

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This functionality could be best achieved with custom sync event receiver that would trigger on item updated. There you could compare before and after events properties to see have the field been modified.

You could maybe achieve that with WF. Problem with WF it will be reactive. You will not be able to stop user from submitting the document/item but it would trigger automatically after that. Then you could query the item history and this way compare the fields. If it wasn't modified it would checkout the document to that user and then send him an email.

Even though second options may be feasible it makes a terrible user workflow. Validation should happen upon submit and that is best place to make it run.

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