Abstract Models for the debonding of a fiber embedded in a brittle matrix are proposed and analyzed. Attention is restricted to systems having a residual compressive stress acting across the fiber/matrix interface. Debonding, as well as pullout after the fiber breaks, is accompanied by frictional sliding. Fiber—matrix interaction is modeled by a cylindrical cell with two sets of boundary conditions: one modeling an isolated fiber—matrix unit and the other a matrix containing an array of unidirectional fibers. The elastic properties of the fiber are taken to be transversely isotropic about the fiber axis, while the matrix is assumed to be isotropic. The debonding process is treated within the framework of fracture mechanics as a mode 2 crack. Two idealizations of friction are considered: a constant friction stress independent of normal compression across the interface, and Coulomb friction. Approximate closed form solutions to the model are presented. These are assessed using results from an accurate numerical analysis.