IMO this is a good example of why Microsoft deserved a lot of their success with Windows 95.

I was a big OS/2 fan at the time, but this is the sort of thing IBM was institutionally incapable of coming up with. Sure, OS/2 supported long file names… if you were on an HPFS file system that (practically) only OS/2 could read. But I'd guess the significant majority of non-corporate OS/2 users dual-booted with DOS. And, IIRC, files with long names were totally invisible to the otherwise superb DOS emulation. And I feel like I even remember some OS/2 programs having trouble with long names because their authors were more likely than not on FAT file systems. So it always seemed more like a "theoretical feature".