Much of the boundary control of wave equations in one dimension is based on a single principle—passivity—under the assumption that control is applied through Neumann actuation on one boundary and the other boundary satisfies a homogeneous Dirichlet boundary condition. We have recently expanded the scope of tractable problems by allowing destabilizing anti-stiffness (a Robin type condition) on the uncontrolled boundary, where the uncontrolled system has a finite number of positive real eigenvalues. In this paper we go further and develop a methodology for the case where the uncontrolled boundary condition has anti-damping, which makes the real parts of all the eigenvalues of the uncontrolled system positive and arbitrarily high, i.e., the system is “anti-stable” (exponentially stable in negative time). Using a conceptually novel integral transformation, we obtain extremely simple, explicit formulae for the gain functions. For the case with only boundary sensing available (at the same end with actuation), we design backstepping observers which are dual to the backstepping controllers and have explicit output injection gains. We then combine the control and observer designs into an output-feedback compensator and prove the exponential stability of the closed-loop system.