Pluggable optoelectronic transceiver modules are widely used in the fiber-optic communication infrastructure. It is essential to mitigate thermal contact resistance between the high-power optical module and its riding heat sink in order to maintain the required operation temperature. The pluggable nature of the modules requires dry contact thermal interfaces that permit repeated insertion–disconnect cycles under low compression pressures (∼10 to 100 kPa). Conventional wet thermal interface materials (TIM), such as greases, or those that require high compression pressures, are not suitable for pluggable operation. Here, we demonstrate the use of compliant microstructured TIM to enhance the thermal contact conductance between an optical module and its riding heat sink under a low compression pressure (20 kPa). The metallized and polymer-coated structures are able to accommodate the surface nonflatness and microscale roughness of the mating surface while maintaining a high effective thermal conductance across the thickness. This dry contact TIM is demonstrated to maintain reliable thermal performance after 100 plug-in and plug-out cycles while under compression.