Confined jet impingement with boiling offers unique and attractive performance characteristics for thermal management of high heat flux components. Two-phase operation of jet impingement has been shown to provide high heat transfer coefficients while maintaining a uniform temperature over a target surface. This can be achieved with minimal increases in pumping power compared to single-phase operation. To investigate further enhancements in heat transfer coefficients and increases in the maximum heat flux supported by two-phase jet impingement, an experimental study of surface enhancements is performed using the dielectric working fluid HFE-7100. The performance of a single, 3.75 mm-diameter jet orifice is compared across four distinct copper target surfaces of varying enhancement scales: a baseline smooth flat surface, a flat surface coated with a microporous layer, a surface with macroscale area enhancement (extended square pin fins), and a hybrid surface on which the pin fins are coated with the microporous layer. The heat transfer performance of each surface is compared in single- and two-phase operation at three volumetric flow rates (450 ml/min, 900 ml/min, and 1800 ml/min); area-averaged heat transfer parameters and pressure drop are reported. The mechanisms resulting in enhanced performance for the different surfaces are identified, with a special focus on the coated pin fins. This hybrid surface showed the best enhancement of all those tested, and resulted in an extension of critical heat flux (CHF) by a maximum of 2.42 times compared to the smooth flat surface at the lowest flow rate investigated; no increase in the overall pressure drop was measured.