We consider the complete set of planar two-loop five-point Feynman integrals with two off-shell external legs. These integrals are relevant, for instance, for the calculation of the second-order QCD corrections to the production of two heavy vector bosons in association with a jet or a photon at a hadron collider. We construct pure bases for these integrals and reconstruct their analytic differential equations in canonical form through numerical sampling over finite fields. The newly identified symbol alphabet, one of the most complex to date, provides valuable data for bootstrap methods. We then apply our results to initiate the study of double Lagrangian insertions in a four-cusp Wilson loop in planar maximally supersymmetric Yang-Mills theory, computing it through two loops. We observe that it is finite, conformally invariant in four dimensions, and of uniform transcendentality. Furthermore, we provide numerical evidence for its positivity within the amplituhedron region through two loops.