InDesign doesn't sort numbers at the beginning of filenames naturally when placing multiple files, instead opting for alphabetical
InDesign CC 2020, 15.1.2 (Mac, but possibly Windows, I can't test)
Place multiple image files where filenames start with increasing numbers (e.g. page numbers).
Expected: files get placed in order 1, 2, 3, ..., 10, 11, ..., 100, 101, etc.
Actual: files get placed in order 1, 10, 100, ..., 2, 20, 200, 201, 3, ..., etc
It doesn't follow the OS implementation of natural order sorting, so placing a lot of images doesn't match the Finder. It instead uses alphabetical sorting, which is counterintuitive.
I have this same problem. It used to work perfectly and now it just places files randomly. This is increasingly annoying with larger projects.
*Edit, updated to clarify terminology and to add new example images