A landing gear monitoring and alerting system includes a locking pin configured to be inserted into an aperture extending through a linkage of an extended landing gear assembly. When inserted into the aperture, the locking pin inhibits movement of the linkage to establish a locked state of the extended landing gear assembly. This system further includes a magnetic sensor and a communication module. The magnetic sensor is disposed proximate the aperture and is configured to sense a magnetic response indicative of the locking pin being disposed within the aperture. The magnetic sensor is configured to generate a sensor output indicative of the locking pin being disposed within the aperture. The communication module has a transmitter coupled to the magnetic sensor so as to receive the sensor output and is configured to responsively transmit a signal indicative of the locking pin being disposed within the aperture.