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Thermal interface materials (TIMs) have become increasingly important in reducing the interfacial thermal resistance between contacting surfaces inside electronic devices, such as at the die-heat-sink or heat-spreader-heat-sink interfaces. While the focus regarding implementing TIMs remains on reducing the thermal resistance path, the long-term performance of the TIM is important from a life-cycle standpoint. This paper presents test and analysis results examining the effect of temperature cycling and elevated temperature/humidity on the thermal performance of filled polymer TIMs using the laser flash method. A three-layer sandwich structure was used to simulate loading conditions encountered by TIMs in actual applications and to assess the change in their thermal resistances. The evaluated thermal resistance included contact and bulk resistances and was calculated using the Lee algorithm, an iterative method that uses the properties of the single layers and the three-layer sandwich structures. Test samples included three thermal putties, a gap filler, an adhesive, a gel, and two gap pads. For most materials, little change or slight improvement in the thermal performance was observed over the course of environmental exposures. Scanning acoustic microscope images revealed delamination in one group of gap pad samples and cracking in the putty samples as a result of temperature cycling. One thermal putty material showed degradation due to temperature cycling resulting from bulk material changes near the glass transition temperature, while other samples showed little change or slight improvement in the thermal performance over the course of temperature cycling.