When multiple images are uploaded at once the first image on the upload page is not the first image temporally, it's the image used to drag the collection into iNat

[jwidness]

Since iNat has no way of knowing whether photos given to it by Windows are in the actual desired order or not, I’m going to go ahead and close this and suggest that further discussion move to the related feature request (https://forum.inaturalist.org/t/sort-by-date-or-file-name-during-upload/1949).