In the early 1990s, scholars talked about Australia’s neglect of South Asia, in particular Australia’s failure to understand the rising importance of India. We spoke of indifference, blind spots, missed opportunities, general indifference and even ideological differences between the two countries that began with Jawaharlal Nehru and Sir Robert Menzies. During the last ten years, Australia’s engagement with South Asia has changed dramatically – Australia has been involved in a counterinsurgency war against the Taliban in Afghanistan intermittently since 2002, and India has emerged as Australia’s fourth largest export market. The paradox that this chapter addresses is the way in which Australia’s strategic engagement with South Asia was dominated by Afghanistan while Australian commercial national interests lay with India. These two relationships have overwhelmingly defined Australia’s connection with South Asia. The focus is on Kevin Rudd’s period as prime minister of Australia (2007–10) and his subsequent role as foreign minister (from 2010), because the Rudd years capture the essence of Australia’s new relationship with this part of the world where some two billion people live.