Within AdS/CFT, we establish a general procedure for obtaining the leading singularity of two-point correlators involving operator insertions at different times. The procedure obtained is applied to operators dual to a scalar field which satisfies Dirichlet boundary conditions on an arbitrary time-like surface in the bulk. We determine how the Dirichlet boundary conditions influence the singularity structure of the field theory correlation functions. New singularities appear at boundary points connected by null geodesics bouncing between the Dirichlet surface and the boundary. We propose that their appearance can be interpreted as due to a non-local double trace deformation of the dual field theory, in which the two insertions of the operator are separated in time. The procedure developed in this paper provides a technical tool which may prove useful in view of describing holographic thermalization using gravitational collapse in AdS space.