The newColumn list entries were made with system.date.format(). The list is not empty, but you’re probably correct that they’re not the Date datatype, but I was still getting errors that had nothing to do with type mismatch. The issue was likely that I didn’t import the java type Date
system.date.format turns date objects into strings (a lossy operation that should only be done at the last possible moment before presentation), so it makes sense you were getting type coercion errors trying to put a string into a date-typed column.