As children develop the abilities to engage in more sophisticated forms of play, play serves as a context in which children can practice and develop skills in various domains including adaptive behavior and executive functioning. StoryCarnival is a tool designed over 39 sessions at a preschool, working with two groups of 3-5-year-old children, with the goal of setting up a specific type of developmentally beneficial face-to-face sociodramatic play similar to Tools of the Mind using 1) e-book stories on which to base play 2) a play-planning tool and 3) a teleoperated voice agent to engage children during play. My dissertation is the result of five years of work aiming to explore StoryCarnival's potential utility in contexts other than the one it was originally designed within. My overarching goal is to identify and make adaptations to the StoryCarnival system to make it more accessible to a broader group of children, more usable by adult facilitators other than the research team who designed it and begin to assess its potential to support holistic skill development in multiple contexts. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]