Note, too, that while Windows 3.1, which observes the 8.3 limit, supports only TTF, the operating systems that can handle OpenType don't have this constraint.

First, file names are arbitrary, and can be changed at will without affecting the font whatsoever (Windows Type 1 pfb and associated pfm fonts must have identical filenames except for the extension). Some of us automatically rename their font filenames to match the font name, using one or another font file renamer utility. That way, one can look at a directory listing and know what font it is., instead of having to open a file such as ABGBI___.otf

It also depends on where the fonts are located! Windows includes all installed fonts Font name ND File name) into a registry entry. Registry entries have a 64K size limit. Installed fonts NOT in the default fonts folder (yes, they don't have to be there) are included in the registry with their full names, including their paths.

FILE names have different restrictions than FONT names, and these vary with the operating environment. For instance, some characters that are legitimate in font names may not be acceptable in file names, and vice versa.