We prove that the Heisenberg Riesz transform is –unbounded on a family of intrinsic Lipschitz graphs in the first Heisenberg group . We construct this family by combining a method from \cite{NY2} with a stopping time argument, and we establish the –unboundedness of the Riesz transform by introducing several new techniques to analyze singular integrals on intrinsic Lipschitz graphs. These include a formula for the Riesz transform in terms of a singular integral on a vertical plane and bounds on the flow of singular integrals that arises from a perturbation of a graph. On the way, we use our construction to show that the strong geometric lemma fails in for all exponents in . Our results are in stark contrast to two fundamental results in Euclidean harmonic analysis and geometric measure theory: Lipschitz graphs in satisfy the strong geometric lemma, and the –Riesz transform is –bounded on –dimensional Lipschitz graphs in for .

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