You should see this message: "There's a problem with the [your device name] that requires it to be updated or restored." This message is not happening.
Not seeing this message: You should see this message: "There's a problem with the [your device name] that requires it to be updated or restored." iPhone plugged right into MB Pro and after I got the picture on my phone showing to plug it into the Macbook and to visit support.apple.com/iphone/restore No message appears and iPhone has gone dark.
MacBook Pro 16″, macOS 10.15