Programs unable to handle 8.3 format filenames co-existing with long filenames.

There is a problem with xcopy program when copying files with 8.3 format MS-DOS-based filename.
To demostrate the problem, I have a directory that has the following files:
When trying to copy those files with xcopy, the following prompt occurs:
This problem also plagued SyncToy 2.1 and NexusFile 5.1.3.
The problem seems to be worse in some program where the program itself doesn’t prompt the user at all and gives no error. For example, in Toucan of PortableApps.com , the program will believe that it completed the copy successfully.
For more information on how 8.3 filenames are generated:

 

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