Supervised agricultural experiences (SAE) have been a core tenet of school-based agricultural education. Despite this, limited evidence has existed regarding the best practices associated with facilitating quality student learning for SAEs at the middle school level. In response, we used self-regulated learning as a lens to examine this deficiency. Leaders of agricultural education from states with the highest middle school agricultural education enrollment and FFA membership nominated exemplary teachers to participate in this study. The qualitative data was analyzed and interpreted through five themes: (1) an eye toward the future, (2) competition as a method of instruction, (3) goal-driven learning outcomes, (4) accountability for student learning, and (5) challenges to facilitating student learning in middle school SAEs. The findings illustrated how the exemplary teachers navigated various contextual and structural challenges to facilitate high-quality learning for middle school students through SAEs. Documenting these practices was a vital step to reimagining SAEs for middle school agricultural education programs. This knowledge could also be used to reposition agricultural education to create a more developmentally appropriate framework that guides the facilitation of learning for middle school SAEs. In the future, research should seek to establish indicators of high-quality SAE programs at the middle school level.