India has been called Australia’s ‘‘neglected neighbor,’’ and many observers complain that it has long lacked the level of official and public interest it deserves.1 Yet for more than forty years, successive Australian governments have sought—periodically but quite sincerely—to engage India and to build stronger bilateral ties, especially in trade and regional security. These attempts at engagement have, admittedly, been fitful, and they have not always borne fruit. Sometimes they have not succeeded for simple reasons: a lack of mutual interests, understanding, or investment; a change of government; or a foreign policy misstep. But the history of these engagements also shows a much bigger challenge for Australian policymakers and those of other middling to small states. Australia’s intermittent engagements of India, this chapter argues, demonstrate above all the problems faced by states beyond India’s immediate region in gaining diplomatic traction in New Delhi. For states like Australia—a ‘‘middle power’’ with limited global influence—engaging states like India is much harder than some observers are willing to acknowledge.2