The article argues that the ecological approach can offer a viewpoint that comprises more educational complexity. If we accept that the observer and object of observation are in a constant relationship, that technology, context and culture are constituting forces of knowledge production, and that theory/practice is another binary divide to overcome, we are forced to address the intertwined emergence of teaching and learning as part of a co-evolutionary process. As part of ecological pedagogy, communication choices focus on feedback, interconnectedness and in-between-ness among living and non-living organisms. By drawing from the encounter between the complex perspective of Gregory Bateson and the thinking of media ecologist Marshall McLuhan, this article focuses on communication choices in teaching. It presents a comparative study on one-to-one programmes in schools in Italy and Brazil and shows the importance of existing connections and communicative exchanges between the elements of a dynamic system.