It is argued that today is an information driven society. Being able to engage digital information abilities to solve an information interaction activity within digital environments is key for social participation, equality and for bridging socio-economic and cultural gaps. Developing these abilities within school classrooms has become a priority. However, research suggest that a majority of students can only complete basic and explicit information-gathering and management tasks within digital environments. Literature constantly holds that students' expressed experiences of information interaction activities are key for developing digital information abilities. Notwithstanding, there are still important gaps within our understanding of students' expressed experiences of them. To address such gaps we employ phenomenography to study Chile's Secondary Technical and Vocational Education and Training students' expressed experiences of information interaction abilities; a group that has likewise been overlooked. By means of purposeful sampling, a total of 24 students participated in the study. Focusing on both the out-of and in-school settings, findings suggest that the apparent clear-cut division between the out-of and in-school experiencing seems not to be as pristine as some might suggest. Findings also indicate that specialty courses, as they are currently designed, might not be favorable for developing digital information abilities as well as pointing towards the importance of situating students' expressed experiences within wider discourses surrounding digital ability development.