Boston Public Schools (BPS) closed for in-person learning in March 2020 due to COVID-19 and didn't fully reopen until the 2021–2022 school year. Due to the age of schools and absent ventilation systems, coupled with decades of disinvestment in the infrastructure, BPS entered the pandemic with serious challenges impacting the health of students and staff. These challenges were magnified by an infectious airborne virus. Instead of using this opportunity to improve ventilation systems, BPS opted to invest in an air quality monitoring system. This system only confirmed what was already known—there is poor ventilation in most school buildings. It did not lead to correction of new or long-standing problems. This failure has harmed the BPS community, which includes primarily low-income Black and Brown families. This article describes Boston's school system, its track record of inadequate attention to infrastructure, and explores pitfalls of focusing on evaluation instead of correction.