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This article provides a case and reviews the considerations involved in acute endovascular stent for penetrating aortic ulcers (PAU)/intramural hematoma (IMH). This case aims to highlight the decision-making and considerations in the acute endovascular management of a patient presenting with PAU and associated IMH. The literature was reviewed including Google Scholar, PubMed, and Embase. Acute aortic syndrome encompasses a spectrum of aortic disease ranging from aortic dissection to PAU and IMH. Whilst classical aortic dissection has been well studied, the PAU/IMH subset of this population is exceedingly rare. Only a handful of case reports have reported on technical considerations for repair. Despite limited natural history data, growing evidence suggests a more aggressive stance is warranted to prevent progression to rupture and late aortic-related mortality. This pathology poses unique challenges in anatomical and technical considerations of repair.