This work considers the problem of multiple detection and tracking in two complex time-varying environments, urban terrain and underwater. Tracking multiple radar targets in urban environments is rst investigated by exploiting multipath signal returns, wideband underwater acoustic (UWA) communications channels are estimated using adaptive learning methods, and multiple UWA communications users are detected by designing the transmit signal to match the environment. For the urban environment, a multi-target tracking algorithm is proposed that integrates multipath-to-measurement association and the probability hypothesis density method implemented using particle filtering. The algorithm is designed to track an unknown time-varying number of targets by extracting information from multiple measurements due to multipath returns in the urban terrain. The path likelihood probability is calculated by considering associations between measurements and multipath returns, and an adaptive clustering algorithm is used to estimate the number of target and their corresponding parameters. The performance of the proposed algorithm is demonstrated for different multiple target scenarios and evaluated using the optimal subpattern assignment metric. The underwater environment provides a very challenging communication channel due to its highly time-varying nature, resulting in large distortions due to multipath and Doppler-scaling, and frequency-dependent path loss. A model-based wideband UWA channel estimation algorithm is first proposed to estimate the channel support and the wideband spreading function coefficients. A nonlinear frequency modulated signaling scheme is proposed that is matched to the wideband characteristics of the underwater environment. Constraints on the signal parameters are derived to optimally reduce multiple access interference and the UWA channel effects. The signaling scheme is compared to a code division multiple access (CDMA) scheme to demonstrate its improved bit error rate performance. The overall multi-user communication system performance is finally analyzed by first estimating the UWA channel and then designing the signaling scheme for multiple communications users.