@agowa338 @lexr @jonty For USB High Speed (480Mbps) signalling to work, the D+/D- pair needs to be close to the right differential impedance (90 ohms) all the way along the signal path.
Proper USB cables have twisted pairs of the right geometry to hit that. A random DB25 serial cable from 1993 does not. So the signal bounces around inside the cable and interferes with itself.
However, the High Speed negotiation only involves a 10kHz square wave. So that bit works, but 480Mbps packets don't.
@destevez This version looks much better to me.
The main thing that still stands out to me is the use of thermal reliefs on the copper pours. In general these are usually best avoided for GHz work. But they do make things easier to hand solder. Again, I don't think it's anything that will stop this board from working, just general advice.