We investigate stability for certain geometric and functional inequalities and address the regularity of the free boundary for a problem arising in optimal transport theory. More specifically, stability estimates are obtained for the relative isoperimetric inequality inside convex cones and the Gaussian log-Sobolev inequality for a two parameter family of functions. Thereafter, away from a ``small" singular set, local C^{1,\alpha} regularity of the free boundary is achieved in the optimal partial transport problem. Furthermore, a technique is developed and implemented for estimating the Hausdorff dimension of the singular set. We conclude with a corresponding regularity theory on Riemannian manifolds. / text