Methods, systems, and techniques for automatically allocating and dynamically determining icons for placement on legacy task output as part of modernizing such tasks are provided. These enhanced modernization techniques may be used for many different applications to automatically provide graphical enhancement to legacy applications in ways heretofore not pragmatically possible because of the sheer volume of menus in typical enterprise scenarios running legacy applications. Example embodiments provide a Role-Based Modernization System (“RBMS”), which uses these enhanced modernization techniques to provide role-based modernization of menu-based legacy applications.