Purpose: It has been demonstrated that AI-powered, data-driven tools' usage is not universal, but deeply linked to socio-cultural contexts. The purpose of this paper is to display the need of adopting situated lenses, relating to specific personal and professional learning about data protection and privacy. Design/methodology/approach: The authors introduce the results of a case study based on a large educational intervention at a fully online university. The views of the participants from degrees representing different knowledge areas and contexts of technology adoption (work, education and leisure) were explored after engaging in the analysis of the terms and conditions of use about privacy and data usage. After consultation, 27 course instructors (CIs) integrated the activity and worked with 823 students (702 of whom were complete and correct for analytical purposes). Findings: The results of this study indicated that the intervention increased privacy-conscious online behaviour among most participants. Results were more contradictory when looking at the tools' daily usage, with overall positive considerations around the tools being mostly needed or "indispensable". Research limitations/implications: Though appliable only to the authors' case study and not generalisable, the authors' results show both the complexity of privacy views and the presence of forms of renunciation in the trade-off between data protection and the need of using a specific software into a personal and professional context. Practical implications: This study provides an example of teaching and learning activities that supports the development of data literacy, with a focus on data privacy. Therefore, beyond the research findings, any educator can build over the authors' proposal to produce materials and interventions aimed at developing awareness on data privacy issues. Social implications: Developing awareness, understanding and skills relating to data privacy is crucial to live in a society where digital technologies are used in any area of our personal and professional life. Well-informed citizens will be able to obscure, resist or claim for their rights whenever a violation of their privacy takes place. Also, they will be able to support (through adoption) better quality apps and platforms, instead of passively accepting what is evident or easy to use. Originality/value: The authors specifically spot how students and educators, as part of a specific learning and cultural ecosystem, need tailored opportunities to keep on reflecting on their degrees of freedom and their possibilities to act regarding evolving data systems and their alternatives.