When changing a field type from Text to Date, where the records contain strings like “1/1/22”. The resulting records contain dates like “01/01/0022”. Converting to ISO date has especially weird results: “1/1/22” becomes “0001-01-22”, but “1/1/99” becomes “1999-01-01”.
I did find a workaround, in case anyone else is looking for a solution to this. Create a formula field with the formula: todate(field("Text Field"), "MM/DD/YY")
(or “DD/MM/YY” if you prefer), then change the type of that field to Date. The todate function seems to get the two digit year right every time.