Win95 is really a GUI on top of DOS. DOS used the FAT file system.
The FAT file system is only able to store file names in an 8.3 format. This means the file name was limited to 8 characters "." then 3 characters.
Win98 introduced FAT32, that allowed the use of long files names. NTFS also has this capability.
To allow users to have long files names, Win95 plays some tricks and matches the real file name to what the user expects. I not sure of all the details of how this was done.
I would expect that what you are seeing in the Samba machine is the real file name. I don't think there is much you can do about this, other than move the user to a later OS.
However I would also expect that the first 6 characters would be the same, and your examples don't show that. I think there was a way of listing the real file names from the command line of Win95. Try reading the help for the dir command.
Check it out and tell us what you find. I might be completely wrong!
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