<p>Teachers' perspectives on education are often overlooked in favour of politically driven global trends that shape education systems across the OECD. Despite visionary expectations of twenty-first century skills, many OECD countries have seen a decline in PISA scores since year 2000. To understand better these tendencies, this study investigated how societal and educational have influenced students' learning and behaviour from the perspective of experienced teachers. Consequently, this study investigated how contextual changes at school and in society reinforce different behavioural and cognitive patterns across student generations. Participants were 812 Norwegian teachers (primary school <i>N</i> = 282, lower <i>N</i> = 226, and upper <i>N</i> = 304 secondary schools) with at least 20&#xa0;years of teaching experience. The study applied a mixed methods approach consisting of thematic analyses of open-ended survey responses that informed four hypotheses for a subsequent SEM analysis. Participants were stratified by region, school type, and economic privilege across Norway, closely aligning with national statistics for representativeness. While some participants noted improvements in today’s students' oral English skills, openness, and presentation skills, most teachers reported declining academic capabilities, intrinsic motivation, resilience and attentiveness, along with increased behavioural and mental health challenges among contemporary students. These issues were mainly attributed to increased digitalisation, permissive parenting styles, egocentrism, and reliance on instant gratification stimuli. The findings call for education—both within and outside of schools—on how societal and technological trends shape students’ behaviour, acquisition, and social skills. The study contributes to identifying, and informing teachers, parents and policyholders about pitfalls and future opportunities in education.</p>