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This paper examines the association between students’ attitudes toward digitalization and their entrepreneurial readiness in Romanian technical and vocational high schools. We analyze 11th–12th graders (16–19) engaged in the Practice Firm (PE) or Firma de Exercitiu (FE) program, a pedagogical simulation of a real company. Using a sample of 700+ respondents, we combine descriptive statistics, contingency tables, and structural equation modeling (SEM) with a sociological reading to map links between pro-digital attitudes, understanding of how firms work, entrepreneurial capital, gender, and residence. Results show that girls report confidence in digital tools comparable to boys, and rural students view digitalization as a way to overcome geographic disadvantages. We frame these patterns as digital symbolic capital: pro-digital attitudes that convert into self-reported readiness within the educational “field” of PE, aligning with diffusion-of-innovation and EU AI/digital literacy agendas.