Although Singapore no longer governs Christmas Island, either on behalf of its British colonial administrators or for itself, some Singaporeans continue to regard it as a lost territory and have false impressions that it once belonged and should again belong to Singapore. By examining this complexity related to Christmas Island and its possible implications for Singapore’s national psyche, this paper surveys the newspapers of Singapore and oral history records of Singaporean ministers and officials for accounts of Christmas Island. It suggests that Singaporean newspapers’ portrayal of Christmas Island as a neglected Australian overseas territory contributed to some Singaporeans’ perception that Christmas Island might actually be better off with Singapore; others even had a misconception of Christmas Island as a lost territory. Such opinions have never really dissipated because the government has never publicly clarified the transfer of Christmas Island and rejected claims about its “sale” to Australia.