Yes, if a horse has hind feet that are typically oblong, the Gloves may not stay on. That can be "disconcerting" to some horses, if it happens at an inopportune moment. My horse has more roundish/triangularish hind feet, so his stay on without a problem. You can add some hardware to the boots to make them stay on better, but really, the shape of the foot is what makes them stay. As for overstriding, you can apply bell boots over the gaiters to help prevent that. Just buy extra large size bell boots.