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Possible side effects of using web job boards in the e-recruitment context, such as candidates dropping out from the hiring process, may emerge if these tools are not transparent about data usage, collection, and processing. In response, we developed a novel web job board designed to enhance transparency, simulating a job-matching recommender system. A qualitative study with 20 Italian participants, combining direct observation of the job board use with the Thinking Aloud protocol and interviews, examines participants’ privacy behaviours in terms of data disclosure and seclusion. Findings indicate a general willingness among participants to share personal data, except for information related to their identity. We found that both the design of the job board and the meanings ascribed by participants to data shaped their privacy behaviours. Features enhancing user understanding of data usage and control of privacy settings were positively received, underscoring the importance of design in fostering thoughtful engagement with job board technologies. We contribute to research on privacy behaviours in the context of job search and we draw suggestions from the study findings on how to design platforms that support data protection and allow safe and purposeful disclosure of personal data, sustaining job seekers throughout the recruitment process.