Learning journal writing is an effective tool to foster the development of reflective capacity in the context of Vocational Education and Training (VET) if conceived as a collection of descriptions and reflections on real professional experiences. Reporting professional situations in a learning journal outside the workplace in turn fosters the connection between places of learning. Taking into account that collaborative writing with peer-feedback stimulates reflective writing and that comparisons between different professional experience boosts reflection, we conducted a study based on peer-to-peer commenting and revising on a reflective journal entry. Considering that this kind of reflection needs to be properly stimulated and scaffolded, we implemented a 3?×?2 study with three different levels of prompts (low-medium-high) for revision and commenting and two kinds of tool (paper-based vs. computer-based). We measured the improvement of the quality of reflection between the initial drafts and the final revised texts on the basis of the reflective grid by Bain et al. (2002). Results show the impact of scaffolding in medium and high scaffolded conditions, whose texts significantly outperformed the low-scaffolded ones in terms of reflection. Revisions and comments are mostly related to the Reporting and Relating dimensions. Moreover, the study confirms the impact of scaffolding on the number of comments produced by peers in the different conditions, but no mediating effect of comments on the text quality was found. The type of tool used has a significant role in determining the quantity of comments developed.