The use of tip mounted winglets with independently variable cant angles was investigated as a means of roll control on wings with an aspect ratio of one. Wind-tunnel testing was performed in which a six-axis force balance was used to measure the total aerodynamic load on wings with winglet control surfaces. Stereoscopic digital particle image velocimetry of the near-wake plane was used to show how the topology of the tip vortices changed with winglet deflection. Shifts in the location of the right tip vortex core are considered to be responsible for roll moment generation because they indicate changes in the symmetry of suction-side flow structures. All winglet deflections were observed to shift the right tip vortex core inboard, and thereby shorten the effective span of the wing. The effect of a winglet deflection may be approximated as a change in the wing aspect ratio and a lateral shift in the wing aerodynamic center. Prandtl’s lifting line theory provides a closed-form estimate for the reduction in lift caused by a winglet deflection. A geometrical argument was made to account for the induced roll moment. The right tip vortex core also shifts vertically, following the deflected wing tip. Vertical shifts in the right tip vortex result in an angle between the wing span line and a line connecting the two tip vortices. A positive angle is defined as the right tip vortex higher over the wing than the left, and it is accompanied by a positive roll moment. While in sideslip, the wing with no winglet deflection experiences a considerable roll moment as a result of a vertical and lateral shift in the two tip vortices. The articulated winglets are observed to partially mitigate these effects when the upstream winglet is actuated, and thus show promise as a direct means of disturbance rejection.