Can we defend 8.3 file names?

My boss still insists on 8.3 file names, "just because ..." and, "you never know...".

If the operating system and tool chain support longer names, and if we have used those for years and seem likely to continue to do so, is there a justification for limiting file names to 8.3?

Give that we can have mandatory 2 or even 3 character file name prefixes, I find it difficult to assign meaningful, descriptive file names.

But, "you never know...".

Is there a justification?