The text above the file drop now says what happens next: every file reaches the column-matching step, and a file from a bank Sheetful recognizes arrives with its columns filled in.
In the preview of your first rows, money in shows with a plus sign, as it does on your transactions list, so it reads apart from money out. A line under the preview says how dates are read: month first, unless the month is written as a name or the year comes first.