Flapping flight has gained much attention in the past decade driven by the desire to understand capabilities observed in nature and the desire to develop agile small-scale aerial vehicles. Advancing our current understanding of unsteady aerodynamics is an essential component in the development of micro-air vehicles (MAV) intended to utilize flight mechanics akin to insect flight. Thus the efforts undertaken that of bio-mimicry. The complexities of insect wing motion are dissected and simplified to more tractable problems to elucidate the fundamentals of unsteady aerodynamics in biologically inspired kinematics. The MAV's fruition would satisfy long established needs in both the military and civilian sectors. Although recent studies have provided great insight into the lift generating mechanisms of flapping wings the deflection response of such wings remains poorly understood. This dissertation numerically and experimentally investigates the aerodynamic performance of passively and actively deflected wings in hover and rotary kinematics. Flexibility is distilled to discrete lines of flexion which acknowledging major flexion lines in insect wings to be the primary avenue for deformation. Of primary concern is the development of the leading-edge vortex (LEV), a high circulation region of low pressure above the wing to which much of the wing's lift generation is attributed. Two-dimensional simulations of wings with chord-wise flexibility in a freestream reveal a lift generating mechanism unavailable to rigid wings with origins in vortical symmetry breaking. The inclusion of flexibility in translating wings accelerated from rest revealed the formation time of the initial LEV was very weakly dependent on the flexible stiffness of the wing, maintaining a universal time scale of four to five chords of travel before shedding. The frequency of oscillatory shedding of the leading and trailing-edge vortices that develops after the initial vortex shedding was shown to be responsive to flexibility satisfying an inverse proportionality to stiffness. In hover, an effective pitch angle can be defined in a flexible wing that accounts for deflection which shifts results toward trend lines of rigid wings. Three-dimensional simulations examining the effects of two distinct deformation modes undergoing prescribed deformation associated with root and tip deflection demonstrated a greater aerodynamic response to tip deflection in hover. Efficiency gains in flexion wings over rigid wing counterpart were shown to be dependent on Reynolds number with efficiency in both modes increasing with increased Reynolds number. Additionally, while the leading-edge vortex axis proved insensitive to deformation, the shape and orientation of the LEV core is modified. Experiments on three-dimensional dynamically-scaled fruit fly wings with passive deformation operating in the bursting limit Reynolds number regime revealed enhanced leading-edge vortex bursting with tip deflection promoting greater LEV core flow deceleration in stroke. Experimental studies on rotary wings highlights a universal formation time of the leading-edge vortex independent of Reynolds number, acceleration profile and aspect ratio. Efforts to replicate LEV bursting phenomena of higher aspect ratio wings in a unity aspect ratio wing such that LEV growth is no limited by span but by the LEV traversing the chord revealed a flow regime of oscillatory lift generation reminiscent of behavior exhibited in translating wings that also maintains magnitude peak to peak.