This dissertation applies theories and concepts of wireless communications and signal processing to the security domain to assess the security of a Wireless secret Key Generation (WKG) system against capable eavesdroppers, who employ all the feasible tools to compromise the system’s security. The security of WKG is evaluated via real wireless measurements, where adversary knows and applies appropriate signal processing tools in ordere to predict the generated key with the communicating pair. It is shown that in a broadband stationary wireless communication channel, (e.g. commercial off-the-shelf 802.11 WLAN devices), a capable eavesdropper can recover a large portion of the secret key bits. However, in an Ultra-wideband (UWB) communication, at the same stationary environment, secret key rates of 128 bits per channel probe are achievable. / Graduate