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  • Have a look at this question Commented Apr 14, 2019 at 13:17
  • arduino_debug.exe is a build of Arduino IDE to debug the Arduino IDE. So normally you should use arduino.exe command for CLI too. The Arduino IDE is a Java application. It has Java bundled in installation. In your case I would guess that the reset of the board is not invoked for some Java related reason. Commented Apr 14, 2019 at 14:01
  • The error message is not related to Java, it's usually either wrong COM port being selected, wrong bootloader or a temporary glitch that resolves when you try to reupload. Commented Apr 14, 2019 at 14:56