An inflatable wrap with automatic tightness detection includes a wrap strap having at least one inflatable sealed zone formed thereon, at least one fluid guiding tube connected to between the sealed zone and an external fluid supply, at least two mating connection elements separately provided on two longitudinally opposite ends of the wrap strap, and a sensor module embedded in the wrap strap. The sensor module includes an output element and a sensor element arranged at locations separately corresponding to the two mating connection elements, and a processor element electrically connected to the sensor element. When the two mating connection elements are detachably connected together to bind the wrap strap around a users body area with the sensor element and the output element becoming aligned with each other to provide an alignment sensing function, it means the wrap strap forms a closed loop structure to provide a proper pressing force.