This chapter investigates key issues arising from ongoing attempts by WTO Members to address the operational dimension of the services waiver granted to least developed country (LDC) Members. It starts off by drawing attention to a number of conceptual and political economy considerations that those responsible for framing specific waiver requests should have in mind moving forward. In doing so, the chapter’s aim is to narrow the scope of the conversation on the services waiver to what could be deemed feasible, mutually acceptable, commercially relevant and development-friendly proposals for its operationalization. While discussions of the services waiver have shed useful light on the potential that services trade holds for the growth and development prospects of the LDC grouping and on the need to use trade as a lever for closer integration of such countries into a rapidly evolving geography of trade, the chapter posits that care is needed in guarding against undue expectations as the central focus of the waiver’s proponents on the expansion of LDC services exports is likely to disappoint absent more concerted efforts to strengthen the often crippling supply side constraints holding back the ability to make commercial (and hence developmental) use of importing country offers.