A medical wetness sensing device includes a cover, a first and second electrically conductive portions housed in the cover, an electrically insulative portion housed in the cover, and a compressible portion. The cover defines an outer surface. The first and second electrically conductive portions are exposed along an inner surface of the device. The first and second electrically conductive portions are configured to transmit a test signal indicating an absence or presence of a liquid on the inner surface. The electrically insulative portion electrically isolates the first electrically conductive portion from the second electrically conductive portion. The compressible portion is flexible, compressible, and configured such that the inner surface of the device is conformable to skin of a wearer of the device. The compressible portion is formed by at least one of the cover, the first and second electrically conductive portions, and the electrically insulative portion.