Using transformative experience theory as a framework, we investigate the potential of utilizing mobile technology and social media to foster deep-level engagement in the form of connections between in-school and out-of-school experience. A ninth-grade Earth science teacher instructed students to take pictures with their mobile devices when they noticed a connection to unit content and upload these with a caption to a private social media group. Analysis of digital artifacts and focus group interviews found that students were inclined to post content from the Internet more than pictures from their everyday experience. Nevertheless, participation in the activity was associated with transformative engagement (i.e., engagement with content in everyday life and expansion of perception and value related to the content). However, participation varied and barriers to engagement were identified.