The focus of this investigation was the development of a methodology to study, evaluate, and support the success of a source-separation plan prior to implementation. A field study of 6 months provided the testing ground to plan, implement, and evaluate a proposed source-separation program, based on this methodology. This program was carried out in a high-performance charter elementary school (Kindergarten-Grade 4, ages 5–10) with 423 students and 45 staff members located within a three-school campus in New York City. The study was directly shaped by the working environment of a multi-campus facility in a municipality that has an established history of mandating and supporting recycling programs. This study focused on identifying and overcoming the obstacles that had prevented the successful fulfillment of existing municipal mandates, with the intention of developing tools to aid the newly created Sustainability Coordinator position. Documenting the difficulties of implementation, while working through the leadership of the administration, highlighted the entrenched complications of working within the traditional administrative framework.