An assembly structured to inflate a retaining or pressure cuff of a medical device of the type associated with artificial airway tube and concurrently monitor pressure therein. A pump assembly is movably connected to a casing and structured to force fluid flow, for inflation of a pressure chamber of the casing. An indicator member is visually accessible through a casing window and is variably positionable dependent on and indicative of existing pressure within the retaining cuff. The existing pressure within the pressure chamber is substantially equivalent to that within the retaining cuff thereby facilitating the variable position of the indicator member being indicative of pressure within the retaining cuff. A junction between the casing and an inflation lumen is structured to allow disconnection and prevent reconnection between the casing and the lumen.