In situ interfacial rheology and numerical simulations are used to investigate microgel monolayers in a wide range of packing fractions, ζ<sub>2D</sub>. The heterogeneous particle compressibility determines two flow regimes characterized by distinct master curves. To mimic the microgel architecture and reproduce experiments, an interaction potential combining a soft shoulder with the Hertzian model is introduced. In contrast to bulk conditions, the elastic moduli vary nonmonotonically with ζ<sub>2D</sub> at the interface, confirming long-sought predictions of reentrant behavior for Hertzian-like systems.