This article is part of a wider research project that has the educational goal of supporting students in the production of conjectures, arguments and proofs, as well as promoting a move from the production of arguments expressed in colloquial registers to arguments expressed in literate registers. In this regard, we Giovannina Albano, Umberto Dello Iacono and Maria Alessandra Mariotti designed and implemented a digital educational environment that allows students to formulate and prove conjectures; three different working areas are available where students can work on a geometrical open problem sometimes individually, sometimes in collaboration. In this article, I report on an empirical study aimed at investigating the functioning of one of these areas, the ‘Working with others’ area, where small groups of students are expected to discuss and formulate a shared solution to a problem. The research question concerns if and to what extent the communication tools, specifically designed to foster students’ collaboration, can promote the production of mathematically acceptable arguments. The qualitative data analysis shows that the ‘Working with others’ area seems to foster discussion within the group and can make students aware of their mistakes. Moreover, it can bring out some students’ misconceptions and can provide useful information upon which the teacher can trigger fruitful discussions. However, this working area does not appear to foster a significant improvement of the production of mathematically acceptable arguments, produced by students in a collaborative and sharing mode. The integration of specific components within this working area seems to be necessary to support the student in moving from argumentation to proof.