A rotorcraft including a main rotor, flight controls connected to the main rotor, a plurality of engines connected to the main rotor and operable to drive the main rotor, a main rotor revolutions per minute (RPM) sensor, and a monitoring system operable to determine an engine failure of the plurality of engines. The monitoring system is further operable to engage an automated autorotation entry assist process in response to at least determining the engine failure and according to the measured main rotor RPM, where the automated autorotation entry assist process comprises the monitoring system generating one or more rotor RPM related commands according to at least a target main rotor RPM and the measured main rotor RPM, where the automated autorotation entry assist process further comprises controlling the one or more flight controls according to the one or more rotor RPM related commands.