This paper considers the gender positioning of white Australian women working on aid projects in East Timor during the military and aid intervention of 2000-2002. Drawing on interviews with women employed in English language teaching programs, I compare the positions women adopted in relation to their engagement with men in the foreign intervention/occupation community and with men in the local Timorese community. From the women’s perspective, the intervention was constructed as patriarchal regime that carried the gendered legacy of an earlier colonial era. This context provided a challenging domain for women development workers, as they juggled often conflicting discourses of gender equality and cultural sensitivity in their relations with men in the community of foreign occupiers, and with local Timorese men. The women’s self positioning in relation to these two groups varied markedly: while they readily rejected the behaviour and attitudes of foreign men as sexist and patriarchal, their response to Timorese men was more complex and ambivalent, demonstrating an awareness of their own inappropriacy as foreign intruders in this space.