This study explored ways in which the arts could be infused into the day-to-day practices of special education teachers and paraeducators to support them in addressing Individual Education Plan (IEP) goals. This study further explored the impact of positive or negative help from teachers, nurses and paraeducators on student engagement. Due to changes in the field (indefinite school closures), half of this project employed remote learning. Findings of the unexpected benefits of observational drawing and portraiture through remote learning were also explored. A communitarian approach to Universal Design for Learning was introduced to two special education classrooms on a suburban high school campus. This intrinsic case study focused on interactions with stakeholders (students experiencing disabilities, teachers, paraeducators, and one-on-one nurses) to better understand their experiences working together. Tools designed to help educators address Individual Education Plans through a creative lens included a template for addressing an IEP goal through a universal design for learning three-step process, a multiple choice survey to help students understand their own learning needs, and a cloud-based ARTS Bank of creative resources for educators to apply to IEPs. Teachers in this project noticed student attention and engagement triple when approaching IEPs through the arts.