The paper attempts to develop an understanding of the planning implications of telecommunication, with a focus on telework in the Australian context. It begins by reviewing major definitional discrepancies in telework studies and provides a definition for telework as a flexible knowledge-work option in the new economy. It then builds upon the growing interest in telework under the National Broadband Network (NBN) in federal policy documents in Australia and analyses the Metropolitan Plan for Sydney 2036 as the major document that shapes the future of Australia's first global city. This analysis identifies serious inconsistencies between federal and state policies and points out a number of policy gaps, regarding the lack of telecommunication awareness at Sydney's metropolitan level. The paper also reveals some opportunities in the current strategyto incorporate telecommunication in dealing with the major planning issues, thus challenging the future of Australia's largest capital city.