Existing research underscores the critical role of the information environment (IE) in shaping students’ transition to university, yet the specific challenges they face in navigating this landscape remain underexplored, particularly in ways that can inform targeted support. This study addresses that gap by examining the experiences of 34 incoming first-year students from Generation Z (Gen Z). Drawing on qualitative interviews, this panel study explores how the shift from a “kind” pre-tertiary IE—defined by clarity, guidance, and reliability—to a “wicked” IE marked by fragmentation and ambiguity creates new difficulties for students in transition. Findings highlight three key areas of change: students’ evolving role from passive recipients to active information seekers, the move from centralised and authoritative sources to decentralised and less structured ones, and a perceived decline in information quality due to the absence of traditional gatekeepers. These insights situate Gen Z’s information practices within a rapidly evolving information landscape during the transition process, underscoring the need for higher education institutions to strengthen informational scaffolding through integrated official platforms, more comprehensive and transparent content, and targeted information literacy training.