With the departure of United Nations peacekeepers, Australia becomes the largest international presence in Timor-Leste. It does so at not necessarily an easy time: despite the stark development challenges that remain, the government in Dili is tired of outside advice. Australia’s past actions over oil and gas in the Timor Sea still cast a shadow over the present. Although Australian aid in Timor-Leste is wide and varied, drawing broad conclusions about its effectiveness and impact is difficult owing to the relative absence of independent evaluations of these programs. Decisions made by each country’s leaders can impact detectably upon the bilateral relationship and complicate the work of Australian government personnel in Dili.