Extending Andreussi and Gurtin’s (1977) pioneering work on the wrinkling of a free surface, we investigate the wrinkling stability of an incompressible elastic-like half-space whose surface is proximate to a contactor. Assuming a plane-strain deformation and accounting for both surface prestress and curvature-dependence of the surface free-energy density, we impose balances of forces and torques both in the bulk and on the surface. From the resulting linearized bulk and superficial equations, we derive a quintic dimensionless dispersion relation and perform a parametric study to see when stable or unstable behavior of the free surface is manifested. In contrast to the quadratic dispersion relation of Andreussi and Gurtin (1977), we obtain a quintic dispersion relation. An anlysis of this dispersion relation shows that the combined effects associated with surface pre-stress, curvature-dependence of the surface free-energy density, and the interactions between the surface and the proximate contactor lead always to an increased number linearly stable wrinkled configurations.