A wireless pressure ulcer alert dressing system for warning a patient or caregiver that soft tissue pressure or health condition has exceeded some predetermined level that over time would necessitate moving the patient to prevent or at least reduce a risk of soft tissue damage. The dressing assembly is adapted to be applied to or near a surface of the patient's body and generate electrical outputs corresponding to soft tissue pressure and other health characteristics sensed at the surface. The dressing assembly generates output signals based on the electrical outputs and corresponding to whether or not the soft tissue pressure has exceeded a predetermined pressure level during the preselected time period. The dressing assembly includes a pocket formed therein for removable, secured and protected insertion of a variety of different sensors such as multiple pressure sensors.