Beyond Digital Natives: A System-Level Analysis of Institutional Barriers and Teacher Experience in Secondary School ICT Integration

(1) Background: Information and Communication Technology (ICT) integration in secondary education remains a critical challenge despite substantial investments in teacher training and infrastructure. This study investigated ICT certification levels, implementation patterns, and barriers among Greek secondary school teachers to understand the disconnect between policy aspirations and classroom realities. (2) Methods: A quantitative cross-sectional survey design was employed with 108 secondary teachers (61.1% female; mean age 47.3 years; 70.4% with >10 years’ experience) in the Prefecture of Ilia, Greece (response rate: 87.7%). Participants were permanent secondary school teachers employed in public schools during the 2021–2022 academic year; substitute teachers and private school staff were excluded. A three-section structured questionnaire was developed through literature review, expert validation (n = 3), and pilot testing (n = 10). Section A assessed demographics (5 items), Section B measured perceived barriers using a 7-item Likert scale, and Section C assessed implementation practices using a 10-item frequency scale (Cronbach’s α = 0.942). Data were analyzed using descriptive statistics, Mann–Whitney U tests, Kruskal–Wallis tests, and correlation analyses. (3) Results: While 74.1% of teachers held Level A certification, only 25.9% achieved Level B, with overall implementation remaining moderate (M = 2.92/5.00). Leadership support deficiency emerged as the primary barrier (76.9%), followed by inadequate technical support (74.1%). Younger teachers (24–35 years) demonstrated significantly higher ICT implementation than their older colleagues (56+ years), and teachers with less experience showed greater implementation frequency than veteran teachers—a finding that paradoxically challenges the “digital natives” assumption, given the barriers they face. Teachers preferred flexible Internet resources to formal educational software, indicating strategic adaptation to institutional constraints. Key limitations include convenience sampling, cross-sectional design, self-reported measures, and regional specificity. (4) Conclusions: The certification–implementation gap reveals that individual competencies cannot overcome unsupportive institutional environments. Effective ICT integration requires systemic transformation, encompassing leadership development, technical support, and structural reforms beyond traditional teacher training approaches.