If the item has license with required additional information on download. And the use has already added that information the user metadata form should be prefilled automatically. But it is not when you EDIT Item -> Upload a file . During uploading a file the license is detached and again attached, that means the user metadata is removed during that process.
https://github.com/dataquest-dev/DSpace/blob/dtq-dev/dspace-api/src/main/java/org/dspace/content/clarin/ClarinLicenseServiceImpl.java#L172