Math proficiency rates are strikingly low for children from high poverty communities. Therefore, it is urgent to find solutions that help them develop basic math skills. Given theoretical considerations about math learning, a potentially promising option is to target children's cognitive engagement. In this study, I investigate a program that was designed to elicit cognitive engagement by encouraging children to take ownership of their learning experiences. The math program provided children with choices while combining learning technology with supportive adults. It was implemented during a summer camp for children experiencing homelessness. Two different online learning software were available for children to choose from, one being a game-based math-practice tool, and the second being an instructional tool. Adult facilitators were recruited to provide individualized support to children. Given the available data, the current study addresses two research questions: (1) what are the characteristics of children who were cognitively engaged, and (2) what was the relationship between engagement and change in math skill? Indicators of engagement reflect the amount of time children spent working on math and their choices within the math program. Children spent an average 18.50 minutes (SD = 5.79) per 40-minute session actively working. When given the choice, children were more likely to choose the game-based math software, but sometimes chose less challenging practice problems within this software. Older children, girls, and children from a rural community worked longest on math (in total and per session), but their choices did not indicate any greater engagement compared to younger children, boys, and children from an urban community. Additionally, children in the program demonstrated improvement in their math fluency scores and maintained their calculation scores. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]