I searched and found that you mentioned in the July 24 site
updates change log that "BUGFIX: Fixed sorting of Files section
Apparently the problem has reappeared. (along with a separate FILES keyword search problem not finding files that are there but that will be in a separate message)
The Upload sort order must be using some other date field for the sorting, because it doesn't sort them correctly, in either ASC or DESC order; or it actually does sort them correctly, but it displays a different (DateUpdated?) field date which results in the list showing like it's not sorted correctly, something to that effect, see attached.
It only happens when the search box is being used, it sorts them correctly if it's not.