Three well-established issues for educational reform to insert middle schooling into the traditional primary-secondary tiers are (a) lack of preservice training of specialist middle school teachers, (b) the absence of clear positive educational outcomes linked to the promotion of middle schooling policy as a philosophy of teaching, and (c) the ad hoc approach to professional development for teachers working within middle schools. Persistent uncertainties about whether middle schooling is an educationally distinctive and developmentally helpful phase of schooling have operated in conjunction with the informal preparation for middle school teaching typical in all western systems of education. These issues can be applied to the recent experiences of Education Queensland teachers with primary and secondary training who have worked within the new middle school environment. A single site investigation at an Education Queensland trial of middle schooling addressed teacher perceptions of how eco-organisational features of a middle school were facilitating or hindering their practice. After individual teachers were primed to be alert to five aspects of middle school ecology, six teams of teachers (n = 21 teachers) discussed summaries of their Likert data and written comment on these categories. Analysis of data indicated ongoing struggles about 'how' to implement middle schooling practice across these eco-organisational features. For such trials of middle years in Queensland to become sustainable educational reform, the experience of these teachers suggests that progressive and integrated approach to micropractice generation needs to temper the open-ended approach to macropolicy advocacy.