Win64 lacks the problem with 255 characters [0]. However, stuff like File Explorer, which the vast majority of my users actually use, can only pass the first 255 characters to the registered application [1], so will Explorer will display stuff with huge long paths, double-clicking that file, or right clicking and "Compress to..." will cause an error.

0 - 32 bit windows will always have this problem.

1 - This is because File Explorer uses a hodgepodge of Win32 and Win64 stuff behind the scenes when running 64 bit windows.