Sony NW A306 – simplify USB transfer
By default, each time you connect Sony Walkman to your macOS (Android File Transfer) it asks for PIN and enforces you to choose connection mode. By default, No File Transfer – just charging. It is possible to override this settings via Developer menu. However, it requires some “magic” to enable it.
If you can’t see Developer Options, while going to
Go to Settings > System > Developer Options > Default USB configuration
you have to scroll down, choose About and then, tap Build number seven times. I know how does it sound. Just trust me :)