Eryk Sun <eryk...@gmail.com> added the comment:

FAT inserts a new file entry in a directory at the first available position. 
(If it's a long filename, this could be up to 21 contiguous dirents for a 
combined long/short dirent set.) This means a directory listing is usually in 
the same order that files were added. One caveat is that dirents for deleted 
files may be reused once there are no more unused entries available in a 
cluster. (I'd expect this depends on the implementation. Also, this is less 
likely with a long filename, since it needs a large-enough contiguous block of 
dirents.) Given a volume with a 4 KiB cluster size, sans overhead there are 127 
32-byte dirents in a cluster.

I used to have an MP3 player that used FAT32 and only played files in directory 
order, so I had to resort directories on disk after adding files. In Ubuntu 
Linux, I see there's a "fatsort" package that implements this. There's probably 
a build available for MacOS.

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<https://bugs.python.org/issue33275>
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