Students entering higher education are expected to transfer information literacy skills and knowledge developed through their primary schooling and sharpened in their secondary years. However, the constant evolution of the information landscape means the mastery of these skills presents challenges for students to develop and teachers to teach. Through interviews, this phenomenological study examines the perspectives and practices of 19 Australian secondary teacher librarians supporting student information literacy skill transfer in school and life contexts and considers important changes in the teaching of these skills. Findings suggest time and content overload are preventing integration across subjects and limiting students' ability to apply skills in real world situations. Further, participants identified changes in important ethical issues around information like copyright and intellectual property, especially for students entering university. Potential solutions to these challenges include the adoption of whole-school or state-wide approaches to information literacy and partnerships with secondary schools and universities.