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A critical need in developing thermal interface materials (TIMs) is an understanding of the effect of particle/matrix conductivities, volume loading of the particles, the size distribution, and the random arrangement of the particles in the matrix on the homogenized thermal conductivity. Commonly, TIM systems contain random spatial distributions of particles of a polydisperse (usually bimodal) nature. A detailed analysis of the microstructural characteristics that influence the effective thermal conductivity of TIMs is the goal of this paper. Random microstructural arrangements consisting of lognormal size-distributions of alumina particles in silicone matrix were generated using a drop-fall-shake algorithm. The generated microstructures were statistically characterized using the matrix-exclusion probability function. The filler particle volume loading was varied over a range of 40%-55%. For a given filler volume loading, the effect of polydispersivity in the microstructures was captured by varying the standard deviation(s) of the filler particle size distribution function. For each particle arrangement, the effective thermal conductivity of the microstructures was evaluated through numerical simulations using a network model previously developed by the authors. Counter to expectation, increased polydispersivity was observed to increase the effective conductivity up to a volume loading of 50%. However, at a volume loading of 55%, beyond a limiting standard deviation of 0.9, the effective thermal conductivity decreased with increased standard deviation suggesting that the observed effects are a tradeoff between resistance to transport through the particles versus transport through the interparticle matrix gap in a percolation chain.