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I recently upgraded from 2016 to 2019, only one content library is of major concern and even that gets minimal use. In any event, previously when a new document was uploaded certain metadata columns were set to required so it would force them to enter some information. Since the upgrade this doesn't happen.

If I look at one of the existing columns it doesn't have the radio button for "Require that this column contains information". If I add try and add a new column just for testing that field is there, it also provides me a lot more options in the "The type of information in this column is" section.

Anyone know how I can get it working like before so when the user uploads a document they have to enter information as the columns are configured.

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This is correct behavior, just like SharePoint Online, required columns are no longer required to be filled out on upload/the document does not remain checked out. Required columns are required to be populated when editing the Properties of the item.

I believe the classic interface may be a solution to this, but haven't tested recently.

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