Finder usb copy issue

[Tech198]

Hi all..

Trying to move .mp3 files from one folder to another on usb, and instead of getting the usual popup of if a file already exists with the same name, it i don't get the option to "keep both".

Yet, when i copy the same file(s) to another usb drive and do the test test (folder to folder) i DO get the "keep both" option.

I just tested this first with one file, but the same problem happens with a few of them. and only happens on this one usb drive.. not from folder on internal nor other usb drive

Can someone explain why this would be ?

Left one is the trouble usb drive copying, right one is another usb drive, same file.

I would prefer to keep both for now

 

[Tech198]

Update: Just to add more confusion to this issue, i can do this under Windows VM just fine, and it does prompt me to "keep both files" even on these 'troubled' files.

ie.. Mac external usb drive is shared to VMWare Fusion, so not really technically windows drive, but the os can do it.