The connection between the adaptor and the GB link cable appears very unstable.
While the USB end can be difficult to fit sometimes, the connection between adaptor and link cable is typically the most reliable part in the chain. The PCB should fit firmly into the plug and have good contact. If you have to "nurse" the connection, a broken cable or worn out plug seems more likely. This happened with my cables a few times.
The tool will indicate that it is connected to the game boy when it is not, As it can just be connected to the Mini Usb adaptor and not the GB.
The tool just says "nanoloop USB-MIDI connected " which means that the nanoloop USB-MIDI adaptor is connected (and not that the adaptor is connected to nanoloop via USB MIDI, maybe that's a little mistakable).There is indeed no two-way connection (except for the nl2 update), data are sent / received blindly. Hence no mention of a Game Boy.