Family engagement has long been held as an important component of the educational experience for our students. This study is about how schools tend to aim towards the middle when looking to engage families in their child's school life, and future implications for how educators need to shift from the lens of the middle-class to reach our underrepresented voices within our communities. This semi-structured, qualitative study had input from 17 participants in a northern Illinois school district that shared their experiences and views with family engagement. Of importance to note, the intended demographic groups to be represented in this study were not represented, as they are historically underrepresented in research, and that was held within this voluntary participant sample. The study's focus shifted to the lens that privilege provides and what that might mean for the families that are underrepresented as schools cater to the middle of the population. The key findings from this research from the privileged perspective were that: a welcoming environment cultivates belongingness, the necessity of having specific communication strategies, that families do not know how to be involved, multiple opportunities allow for families to be more involved, perception goes a long way in people telling your story, and that partnering with parent organizations to provide ways that families can be involved is essential. The implications of these findings are that schools tend to norm towards the middle class, which while commonplace, is hidden in plain sight and should be noted by educators to avoid that pitfall. Additionally, maintaining engagement as children age up through middle school is a task that schools need to focus upon to maintain the connections between school and home. Also, the guidelines that schools seem to provide for our middle-class families in terms of involvement would do well to cater to all of our families. Finally, this research showed the need for further research in a longitudinal type study to capture the voices of all families and how schools can best meet their needs in engagement. [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/en-US/products/dissertations/individuals.shtml.]