Embodiments of negative pressure wound therapy systems and methods for operating the systems are disclosed. In one embodiment, a negative pressure source can provide negative pressure via a fluid flow path to a wound dressing comprising a stabilizing structure. The stabilizing structure can be inserted into a wound and collapse upon application of negative pressure to the wound when the stabilizing structure is positioned in the wound. A controller can in turn determine a measure of collapse of the stabilizing structure from a pressure in the fluid flow path while the negative pressure source maintains a magnitude of the pressure in the fluid flow path within a negative pressure range. The controller can output an indication responsive to the measure of collapse.