We consider antiparallel Wilson lines in N = 4 super Yang-Mills in the presence of a codimension-1 defect. We compute the Wilson lines’ expectation value both at weak coupling, in the gauge theory, and at strong coupling, by finding the string configurations which are dual to this operator. These configurations display a Gross-Ooguri transition between a connected, U-shaped string phase and a phase in which the string breaks into two disconnected surfaces. We analyze in detail the critical configurations separating the two phases and compare the string result with the gauge theory one in a certain double scaling limit.