This qualitative study examines how content strategies deployed on Instagram influence the engagement of Generation Z (born between 1997 and 2012) towards e-learning platforms. Twenty semi-structured interviews were conducted with 10 university students and 10 young Tunisian professionals, until data saturation was reached, and then manually analyzed according to the thematic analysis method of Braun and Clarke (2006), with independent double coding to ensure the reliability of the interpretation. Three main results emerge. First, advertising effectiveness on social networks follows a two-step mechanism: a passive awareness phase that builds awareness, followed by an active search phase that triggers conversion once the need for training has become conscious. Secondly, the mobile phone has become the central means of access to online learning platforms, which poses a strong requirement for technical simplicity. Finally, the authenticity of branded content and the opinions of other learners act as a signal of perceived risk reduction and weigh more heavily in the final decision than the advertising speech itself. These results make it possible to propose six concrete recommendations, accompanied by monitoring indicators, for e-learning organizations seeking to better reach this audience. The study also reminds us that Generation Z is not a homogeneous bloc: behaviors vary according to field of study and professional situation more than according to age, which calls for more differentiated messages than existing literature suggests.