Children have frequent access to technologies such as computers, game systems, and mobile phones (Sefton-Green, 2006). But it is useful to distinguish between engaging with technology as a "consumer" and engaging as a "creator" or designer (Resnick & Rusk, 1996). Children who engage as the former can use technology efficiently, while those who engage as the latter are creative and adaptive with technology. The question remains of how best to encourage movement along this continuum, towards technological fluency. This study defines three habits of mind associated with fluent technology engagement [(1) approaching technology as a tool and a creative medium, (2) understanding how to engage in a design process, and (3) seeing oneself as competent to engage in technological creativity], and examines the implementation of a learning environment designed to support them. "Robot Diaries," an out-of-school workshop, encourages middle school girls to explore different ways of expressing and communicating with technology, to integrate technology with personal or fictional storytelling, and to adapt their technical knowledge to suit their own projects and ideas. Two research purposes guide this study. The first is to explore whether "Robot Diaries," which blends arts and engineering curricula, can support multiple pathways to technological fluency. The second purpose is to develop and test a set of instruments to measure the development of technological fluency. "Robot Diaries" was implemented with a group of seven home-schooled girls between the ages of 9 and 14. Instructors from a home school enrichment program ran the workshop. The study utilized a mixed methods approach. Analysis suggests two distinct patterns of engagement in "Robot Diaries" are possible--an engineering focus (characterized by attention to the structure and function of the robot) and an artistic focus (characterized by attention to the robot's representational capacity). The ability to support and sustain multiple levels of participation is an important quality in a workshop designed to broaden engagement in technology exploration activities. Pre-post assessments suggest changes in confidence and (to a lesser extent) knowledge. This study has implications for the design of learning environments to support technological fluency, and for measuring this construct. [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.]