Engagement among adolescents is a crucial factor for identity formation and positive youth development (Barker, 2015; Kegan, 1994). To help address disengagement, socially engaged art education (SEAE) practices have emerged, combining art with action-oriented curricula to critically examine the community and connect to it through meaningful experiences (Helguera, 2011). This current study aimed to better understand how the social dynamics at school and in the student’s own neighborhood impacted the roots of engagement, particularly from school and the larger community, and to address the need to understand interventions that engage, such as those led by art. To study youth engagement in the context of disenfranchised school environments, I designed a pragmatic informed participatory research study, which included six art-infused civic activities that incorporated reflection, action, and artful dialogue framed by Reason’s (1994) co-operative inquiry process. Through this research approach, I explored the perceptions that 16 12th-grade high school students had about their community and their desire to connect and to serve. Using an embedded mixed-methods design (Creswell, 2014), the art-infused civic activities and data collection took place simultaneously. The methods used included questionnaires and surveys, field observations, participant-produced documents, visual methods, interviews, and focus groups. An analysis of the data yielded several findings regarding the participants’ perceptions and connections to their community. For the participants in this study, community was the product of finding and discovering commonalities and feeling safe, as well as having opportunities to attain new skills. The students identified a lot of deficiencies at school, which led them to feel that school was not part of their community. However, despite this apathy, the students expressed appreciation for opportunities that allowed them to bond with their peers and teachers. Engagement in the art-infused civic activities resulted in students attaining newly formed perspectives about their peers and the school staff. The participants reported viewing them as having the capacity to show a caring side. Through these activities, they also saw themselves as more empathetic and able to make an impact in their community. Although some of the participants had been involved in service activities prior to this study, they felt that in this study the experiences were more meaningful because they were able to reflect and understand the magnitude of their contribution. Even though most participants expressed having a desire to help both their community and school, they also felt that this could not be accomplished until they became financially stable. This study contributes to the field of art education by examining the viability of art projects that aim to address youth disengagement, and to better understand the impact that art education has on youth engagement dynamics in the context of low-SES communities.