We present the Cone of Darkness, an application to automatically configure blank-sky positions for a series of stacked, wide-field observations, such as those carried out by the SAMI instrument on the Anglo-Australian Telescope (AAT). The Sydney-AAO Multi-object Integral field spectrograph (SAMI) uses a plug-plate to mount its core imaging fibre bundles (hexabundles) in the optical plane at the telescope's prime focus. To make the most efficient use of each plug-plate, several observing fields are typically stacked to produce a single plate. When choosing blank-sky positions for the observations it is most effective to select these such that one set of 26 holes gives valid sky positions for all fields on the plate. However, when carried out manually this selection process is tedious and includes a significant risk of error. The Cone of Darkness software aims to provide uniform blank-sky position coverage over the field of observation, within the limits set by the distribution of target positions and the chosen input catalogues. This will then facilitate the production of the best representative median sky spectrum for use in sky subtraction. The application, written in C++, is configurable, making it usable for a range of instruments. Given the plate characteristics and the positions of target holes, the software segments the unallocated space on the plate and determines the position which best fits the uniform distribution requirement. This position is checked, for each field, against the selected catalogue using a TAP ADQL search. The process is then repeated until the desired number of sky positions is attained.