Okay, to answer the questions:

Yes, it played in MediaMonkey when I did try to use the right-click menu.
And they did scan and work properly in MM5 (5.0.0.2227)

So, that's good, at least.

Hi,
Windows Support for long long filenames is always erratic. Sometimes work sometimes no.

I have even created App that creates 4096 Long path and saves 2 bytes TXT in end result.

Even File explorer (Win 10 Pro v1909) have issue handling the file, but I can work with folders and rename them.

Only way to delete the file and path is to use my app. Total commander also warn that path is longer than 255, many installs do not work with long paths.

It is hit and miss. Usually if you can drag and drop file to MMW Now playing it can handle Long path.

Have you tried MM5 as it has improved Long path handling?

That looks like it's 248 characters long which is within the 255 limit (Windows used to have). Can MediaMonkey play the file if you open it from File Explorer with MediaMonkey?

Windows 10 Pro - 1909
Media Monkey Gold - 4.1.26.1896

Sufficiently long file names are skipped when I scan directories. I did a quick search in the forums and didn't see it mentioned.
I've seen this with a few files.
What's interesting is that I can tell what files are affected, because on the file properties, Windows shows the old 8.3 file format for names as you can see in the path in the image I'm including.

[img]https://i.imgur.com/XgolbGY.png[/img]

In this case, the original file path is:
D:\Dumps\Music Dumps\HalloweenBooootie6\05 Titus Jones - Look What Halloween Made Me Become (Rob Zombie vs. Taylor Swift vs. Rihanna vs. Imagine Dragons vs. John Carpenter vs. Kesha vs. Three Days Grace vs. Katy Perry ft. Juicy J vs. Deadmau5).mp3

But the path in the properties panel truncates them to:
D:\Dumps\MUSICD~1\HALLOW~2\HALLOW~1

If I shorten the file name, the file will scan as usual.