Various copper and silicon based thermal management systems are used in the cooling of electronics. However, the rigid nature of these materials along with their high thermal and electrical conductivity pose a difficulty in developing direct contact embedded flexible cooling systems that can offer robust cooling performance. The low density, thermal stability, chemical inertness, and electrical insulation of Polydimethylsiloxane (PDMS) make it an ideal material to develop lightweight direct contact thermal management systems for electronics. Its ease of fabrication with tunable flexibility provides the opportunity to go beyond traditional electronics and develop advanced active and passive thermal management systems for a wide–range of applications in foldable and wearable electronics, liquid cooling garments, microgravity, and electric motors. In this study, a flexible PDMS based microchannel with micropillar arrays, which enhance the thermal performance of the device through capillary-assisted flow, has been developed. The hydrodynamic and convection heat transfer performance of three PDMS wick pillar geometries, ranging from a porosity of 0.8–0.91, are investigated and compared under single-phase and two-phase conditions. Dielectric coolant FC-3283 is employed and permeability measurements are made for mass fluxes ranging from 53 kg/m2 s to 369 kg/m2 s. Given its conformability, the device demonstrates a deviation from Darcy’s Law, within the laminar regime, with an increasing permeability with mass flux at the rate of ∼0.5–0.8 Darcy/(kg/m2 s). A semi-analytical model has been developed and reported to quantify the conformability of the device. The heat transfer performance is experimentally evaluated using the same dielectric fluid for mass flux ranging from 105 kg/m2s to 420 kg/m2s with heat fluxes ranging from 1.5 W/cm2 to 16 W/cm2. Heat transfer coefficients of up to 7000 W/m2 K are observed, which are comparable to copper and silicon microchannels. The effect of porosity on the single phase thermal performance has been evaluated against the pumping power to provide a basis for thermal management system design. High-speed imaging is performed to study the two-phase flow characteristics to provide insight into the vapor formation and removal.