This research study examined the design of a virtual keyboard that can be used for text entry with a rotary controller, particularly for users who may differ in age and experience with a particular system. Features of a virtual keyboard that have been shown to affect the individual movement and visual search components of the text entry task were assessed for younger and older adult users. Participants entered words by finding and selecting individual letters with a rotary controller on a keyboard arranged alphabetically or following the standard QWERTY keyboard. Performance was examined across different levels of experience with the task. We found that experience independently interacted with shape, arrangement, and age group. Both age groups improved their entry time overall and at each measurement period, but older adults learned more slowly. Although performance improved for both arrangements, the Alphabetic arrangement was significantly faster. Neither shape was significantly faster, but results suggest that the more salient corner features on the Plus facilitated memorization and retention.