First, are you sure you're launching the correct Simulator and it's in the PlaydateSDK/bin/ folder. If you're opening a random Sim it will prompt for the SDK location. If you are sure you're launching the correct one and you're still seeing this issue, the easiest way to fix this is delete the Sim settings file found in '-your home folder-/AppData/Local/Playdate Simulator/Playdate Simulator.ini'. Hope this helps.