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Adolescents with learning difficulties are at risk of leaving school without a qualifying certification. They may experience difficulties in entering the labour market. In Quebec (Canada), the Work-Oriented Training Path (WOTP) enables these young people to develop their employability by offering pre-work traineeships in actual companies. The aim of this pilot study was to develop an innovative intervention based on using technological aids to help students enrolled in the WOTP programs developing work skills.Eight teachers and fifteen students enrolled in the WOTP participated in a multiple case study. Teachers first attended a training workshop and were then asked to apply a method to conduct workplace analysis and technological aid allocation for two students. They were free to choose any applications. Each two months, a collective meeting was organised to share the various experimentations; the content of meetings was recorded and analysed. Additional data was collected along the study (log book, questionnaires, interviews). Data triangulation led to a portrait of utilisation barriers and facilitators. Findings were used to establish specifications for future intervention.According to teachers, the principal needs of their students are related to spatial and temporal organisation, execution speed, motor skills, communication difficulties, and learning transfer in various contexts. Teachers mostly used simple, usual and free apps, like calendar, notes, alarm functions, checklists, and few more complex apps that required programming, as My video coach, Shadow Puppet, Explain Everything. The main difficulties with technological aids encountered by teachers concerned the relationship with traineeship companies, implementation time and the degree of involvement of students.Two principal stakes emerged from this study. If they are to be used in workplaces, technologies must (1) be operative (i.e. useable and useful at the moment required), and (2) be used autonomously by students in workplace for subsequent mobilisation.