Table sorting by types 'User Email' and 'Date' are incorect

I have a table of aggregated data and have several columns that all sort by mapped value. I have two columns, one of type 'User Email' and one of type 'Date' that both sort incorrectly. However, I know the mapped values are correct because when I change both columns to type 'Text', they sort the data correctly. I suspect the problem is stemming from how Retool parses raw data into certain data types. For the 'User Email' column it's find to use type 'Text', however I would prefer to use 'User Email'. And my 'Date' column cannot be raw text as it would very difficulty for users to read the table. Any solutions or ideas what could be going wrong?

Screenshot from 2022-08-04 13-21-08
Screenshot from 2022-08-04 13-19-21
Screenshot from 2022-08-04 13-19-02