Improving milking system performance through the incorporation of a source of greater than atmospheric pressure air into a pulsator while limiting total pressure in the teat cup. The system is further improved by providing an improved supply of regulated vacuum to the milking cluster throughout the milking process. The system is further improved with a monitoring and detecting the functional failure of the pulsation assemblies. Additional system improvements are provided with the addition of a fresh air valve assembly, a wireless method of regulating vacuum levels and the remote location of a pulsator assembly in a basement style parlor.