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We compute the two-loop result for the null pentagonal Wilson loop with a Lagrangian insertion (normalized by the Wilson loop without insertion) in planar, maximally supersymmetric Yang-Mills theory. This finite observable is closely related to the Amplituhedron, and it is reminiscent of finite parts of planar two-loop five-particle scattering amplitudes. We verify that, up to this loop order, the leading singularities are given by the same conformally invariant expressions that appear in all-plus pure Yang-Mills amplitudes. The accompanying weight-four transcendental functions are expressed in terms of the pentagon functions space known from planar two-loop five-particle amplitudes, but interestingly only a subset of the functions appears. Being a function of four dimensionless variables, the observable has interesting asymptotic limits. We verify that our analytic result is consistent with soft and collinear limits, and find an intriguingly simple pattern in the multi-Regge limit. Thanks to the new result we can also conjecturally predict, for general kinematics, the maximal weight piece of the planar three-loop five-particle all-plus amplitude in pure Yang-Mills theory. Motivated by the Amplituhedron geometry, we investigate positivity properties of the integrated answer. Generalizing previous results at four particles, we find numerical evidence that the two-loop five-particle result has uniform sign in a kinematic region suggested by the loop Amplituhedron.