Mirror is aware when it can't get the USB connection to Playdate (because something else is using it, eg. Simulator) and prompts
The same does not apply to Simulator, which is not aware of the USB connection being in use and you have to wait for things to timeout when trying to upload a game, etc.
So my request is for the Simulator to be more aware of the USB status.
For example not start the upload process if it can't get the USB connection.
And/or show a warning like Mirror does.