Abstract: As part of its economic diplomacy, Australia has directed intense effort into both bilateral and plurilateral trade negotiations such as the Trans-Pacific Partnership. According to then Minister for Trade and Investment Andrew Robb, with no major multilateral trade deal in decades, you have to ‘row your own boat’ or risk missing out. With the fundamentals of trade and the nature of trade negotiations changing, trade liberalisation has become an increasingly sophisticated and difficult negotiating area. A case study of the controversial TPP shows the tensions for a middle power navigating this space. The benefits of the TPP are contested and the government faces criticism of the adverse impacts of the agreement, especially investor-state dispute settlement clauses, impact on human rights and suspicion that the TPP is motivated by geopolitical drivers. In order not to lose more than it gains in moving away from the multilateral trade system, Australia must ensure that trade agreements are consistent with WTO rules and have open and fair accession regimes as a basis for signing. Finally, there is the need for higher levels of transparency and democratic accountability than has historically applied. A new white paper is necessary to make the case for trade liberalisation.