A freezeless hydrant maintenance system for testing, troubleshooting, and repairing the functionality of a freezeless water hydrant prior to the seasonal freezing temperatures, the system comprising a pressure vessel adapted to receive and hold a fluid under pressure, an actuator adapted to release the pressurized fluid upon the user's command, at least one display and an adapter hose adapted to engage a hydrant and seal to prevent pressure loss, whereby the system is attached to a freezeless hydrant, the user opens hydrant pressurizing the vertical pipe and hydrant with water and air, observes the display determining if the freezeless hydrant drain hole is block, then operates the system applying additional pressure to clear blockage, and identifies a hydrant that needs replacement.