Metastability is a phenomenon that can cause system failures in digital circuits. It may occur whenever signals are being transmitted across asynchronous or unrelated clock domains. The impact of metastability is increasing as process geometries shrink and supply voltages drop faster than transistor Vts. FPGA technologies are significantly affected since leading edge FPGAs are amongst the first devices to adopt the most recent process nodes. In this paper, we present a comprehensive suite of techniques for modeling, characterizing and optimizing metastability effects in FPGAs. We first discuss a theoretical model of metastability, and verify the predictions using both circuit level simulations and board measurements. Next we show how designers have traditionally dealt with metastability problems and contrast that with the automatic CAD algorithms described in this paper that both analyze and optimize metastabilityrelated issues. Through our detailed experimental results, we show that ...