This talk considers a number of projects in Technology Enhanced Learning (TEL) that have focussed on designing advanced digital tools that stimulate and support dialogue rich learning. These have emphasised collaborative thinking and meaning making in a rich and varied range of educational contexts. Technically, they have exploited AI, CSCL and HCI techniques, and ongoing projects are incorporating social software and semantic technologies. To address the particular challenge of extending this line of work within the Web 2.0 landscape and beyond, where the pace of technological change is profound and the presence of social media is substantial, I will introduce the original notion of Deep Learning Design (DLD) that we have been developing at the LTRI (e.g. Ravenscroft 2009; Ravenscroft & Boyle, 2010). This is a paradigm that we hold is important to both better understanding and realising learning in the digital age that counters the sort of technological determinism that is unhealthy for the field of learning. So this talk will: consider the current challenges of designing engaging, social and media-rich learning; explain why the challenges raised necessitate the introduction of an original conceptualisation of design; and, exemplify and map this new notion of design to three large-scale TEL initiatives. These are projects in Digital Dialogue Games (DDGs), an EC IP - MATURE: Continuous Social Learning in Knowledge Networks and a Centre of Excellence in Re-Usable Learning Objects.  Finally, I will synthesise reflections on the challenges raised by these initiatives through considering an agenda that moves towards a smarter web for learning in the 21C.