School fundraising is a practice that is common in many schools in the United States. This is also true in high-poverty schools where there are many financial needs that are often not met. Lincoln Elementary School is one of these schools. A well-intentioned first-grade team of teachers develops and works to implement a plan to fundraise using their students to get monies for needed classroom technology. A problem arises when the reward designed to incentivize students to raise funds is put into question by one of the first-grade student's parents. This complex case considers inequity, fundraising, intentions, principal decision-making, critical consciousness, and leading high-poverty schools using a lens of social justice.