At the dawn of the new millennium, Prensky (2001a; 2001b) popularized a view of the younger generations as “digital natives”. While this myth has not gone unchallenged (Prensky, 2009; Thomas, 2011), students have since then been acritically assumed to be almost naturally fluent ICT users. However, recent studies have revealed that this is not always the case. As far as Web search in particular is concerned, a tendency has been shown towards a simplistic “get in, get the answer, get out” approach (Thompson, 2013, pp. 20–21) which prevents them from taking full advantage of the Web’s potential for autonomous learning. In this context, this chapter advocates the importance of familiarizing students with advanced Web search skills as an opportunity for a rewarding accessible DDL experience while also contributing to their development of critical reasoning.