Medical dressings including stiffening systems fixedly attached to backing layers are described herein along with methods of using the medical dressings. The stiffening system is fixedly secured to the backing to limit flexing and stretching of the backing layer. Typically, the medical dressing and stiffening system is applied over a medical device that is secured to skin. The stiffening system covers some of the medical device and also extends beyond the medical device. The stiffening system stabilizes the medical device over the skin.