A monitoring system for a work vehicle having a lift system to which an implement is attachable via a connection assembly includes a weight detection subsystem operable with the lift system and configured to transfer signals representative of a weight supported by the lift system. The monitoring system also includes a position detection subsystem operable with the connection assembly and configured to transfer signals representative of a state of the connection assembly. A controller is in operable communication with the weight detection subsystem and the position detection subsystem and is configured to receive signals from the weight detection subsystem and from the position detection subsystem, determine a condition of the connection assembly based on the signals received, and output a signal based at least in part on the determined condition.