Time to try different cables and ports. I have a bunch of weird stuff that went on, and I found one cable that always works. If it's a hint the wire is thick.

The reason the Y cable is short is to keep down the electrical loss over the distance.

I have ports on one machine that work with my DSLR fine, but not the hard drive, and not my blackberry. It's a crap shoot. If it's the black hard drive see if you can get the end with the connection off and try and push the wires in, make sure the contact is good.

Once it works copy it to something more robust.

John Conley
Musica est vita