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Background: Inferior petrosal sinus sampling (IPSS) is a useful technique in the diagnosis of Cushing's disease (CD) when the imaging finding is negative or equivocal. Different authors have reported considerable variability in the ability to determine tumor laterality with IPSS. Here the authors present a retrospective case series of 7 patients who underwent IPSS using a systematic algorithm to improve lateralization accuracy by identifying optimal sampling sites on the basis of individual cavernous sinus drainage patterns in each patient., Observations: Of the 7 patients identified, 6 were determined to have CD and subsequently underwent surgery. IPSS was accurate in all patients from whom laterality was predicted. Arterial and venous angiography were used to define cavernous sinus drainage patterns and determine optimal sampling sites. All patients who underwent surgery achieved hormonal cure., Lessons: All IPSS predictions of lateralization were correct when available, and all patients who underwent surgery achieved hormonal cure. Advances in angiographic techniques for identification of the site of primary drainage from the cavernous sinus and subsequent optimization of microcatheter placement may improve the ability to predict tumor laterality., Competing Interests: Disclosures The authors report no conflict of interest concerning the materials or methods used in this study or the findings specified in this paper., (© 2021 The authors.)