This graduation project examines the usability of the Properties Panel in Adobe Illustrator, a central yet often challenging component of professional design workflows. While novice users face steep learning curves due to dense layouts and low discoverability, expert users encounter inefficiencies caused by inconsistent contextual behavior and fragmented tool placement. The project explores how anticipatory design can improve adaptability across skill levels. Based on in-depth user research, usability testing with new, novice, and expert users, and comparative analysis of similar tools, the study identified gaps in responsiveness, accessibility, and task alignment. Eight anticipatory features were proposed, including behavior-driven personalization, contextual highlights, predictive tool surfacing, and collapsible groupings. A key outcome, Focus Mode, enables customizable workspaces with pinned actions, swappable sections, and shortcut mapping. Task-based validation showed improved efficiency, recall, and satisfaction, demonstrating how context-aware interfaces can make creative tools more inclusive and scalable.