Design of tall buildings, based on performance of the structural and non-structural elements, especially against wind hazards, has recently received relevant attention by researchers. Among all studies, the importance of “wind-borne debris” has been emphasized. A debris object becomes air-borne due to high winds (hurricanes). This flying debris can impact against the façade of a building. The debris-induced damage is critical for the envelope of a tall building. Most studies, which are currently available, concentrate on the trajectory estimation of the debris, and the risk of impact and damage for residential low-rise buildings. In most cases, trajectory prediction relies on the assumption of a uniform horizontal wind field without turbulence. Less attention has been devoted to simulating trajectory in a fully turbulent wind field. In the first part of this presentation, probability damage analysis was conducted for a 183-meter tall building; turbulence effect was neglected and impact and risk analysis was performed both in 2D and 3D flows. As a result, a “universal impact curve” and a series of “iso-probability impact contours” were derived. In the second part, the effect of a vertical “sudden” gust was incorporated in the trajectory modeling and estimation. A simplified model of this vertical-velocity gust, designated as “Kussner-Like” vertical gust model, was used to simulate, perhaps more realistically, wind-driven trajectory of compact objects in the atmospheric boundary layer.