Short filenames are only created when files are created, copied or moved. Enabling short filenames won't cause Windows to scan the drive adding short filenames to all files that don't have them.
Move those 20 files to another directory, then move them back, and the short filenames should appear.
Beware though that enabling short filenames imposes a drive speed performance penalty.
"This all reminds me when i took the windows vista sticker thingy off my old laptop, and on my washing machine as a joke. A few days later said washing machine stopped working. I still think this cannot be a coincidence."