Hes not gonna drive it.

It is 26 years old. That is a quarter of a century. Just like a 1975 song was called an “oldie” in 2000, it’s fair to call this an oldie now.

Edit: “What’s my age again” is closer to ABBA’s “Waterloo” than it is to today.

This looks like Voyager but it might be an instance setting.
Edit: it is an experimental setting in voyager.

From a technical standpoint, the windows NTFS filesystem is designed inherently case sensitive, just windows doesn’t allow creating case sensitive files.

Connecting an NTFS drive to linux, you can create two separate files readme.txt and Readme.txt.

Using windows, you can see both files in the filesystem, but chances are most (if not all) software will struggle accessing both files, opening readme.txt might instead open Readme.txt or vice versa.