Cerebral microbleeds (CMBs) are considered as a marker of cerebral microangiopathy. CMBs can be detected in various clinical conditions, with the most common being cerebral amyloid angiopathy and chronic hypertension. Uncommon causes of CMBs include cerebral autosomal dominant arteriopathy with subcortical infarcts and leukoencephalopathy, Moyamoya disease, Fabry disease, fat embolism, infective endocarditis, prosthetic heart valves, posterior reversible encephalopathy syndrome, brain radiation, cocaine abuse, thrombotic thrombocytopenic purpura, traumatic brain injury, obstructive sleep apnea, and genetic syndromes related to missense mutations of collagen. In this review, after discussing the causes related to CMBs, we present two cases of patients with a history of aortic dissection that underwent brain magnetic resonance imaging for the investigation of acute onset neurological symptoms. Susceptibility-weighted-imaging (SWI) sequences disclosed multiple, small-sized CMBs located predominantly within hemispheric cortical and subcortical areas, with a pattern of preferential involvement of watershed arterial territories. Although both patients had a history of well-controlled arterial hypertension, the pattern of CMB distribution was distinct to that typically observed in chronic hypertension, which is mainly associated with deep or infratentorial CMBs, as well as with matter hyperintensities and lacunes. The differential diagnosis of diffuse CMBs on brain SWI may also include the history of aortic dissection. The patient's history, in association with the pattern of spatial distribution of the lesions on magnetic resonance imaging-SWI, is usually informative.