In this research project we describe the legacy software landscape, its current state, and challenges associated with aging information systems and access to its data. We briefly describe the popularity of dynamic languages and how a specific dynamic programming language, Ruby on Rails (RoR or Rails), is used to create a system to extract data from a legacy system to increase efficiency and productivity in an academic class scheduling system. As an example, we describe, first, how a system developed in Rails, called Class Scheduler, pulls data from a legacy student management system (MAPPER) developed in Tcl (pronounced "tickle") and uses this data to vastly increase the efficiency of the scheduling process and, second, how it reduces conflicts in class schedules. We discuss the advantages of automatically extracting and processing the data from the legacy system and the limitations associated with this process.