The purpose of this article is to report two distal dissections resulting as a complication of endovascular aneurysm repair (EVAR) in two cases of type B aortic dissection (TBAD) and its relationship with prosthetic alignment at the distal landing zone. Two patients affected by aneurysm formation of a chronic type B dissection underwent EVAR. During postoperative follow-up, at 48 and 39 months, respectively, a new chest pain episode recommended a new computed tomographic angiography examination. New false lumen reperfusion and increased aortic diameter distally to the prosthesis were demonstrated. The distal end of each stent graft showed an angulated alignment to the proximal descending aorta at the point of the secondary entry site. Both patients were successfully treated after deployment of a distal endograft. Prosthetic alignment with the aortic axis is important to avoid wall stress and secondary perforation in patients treated for TBAD. The distal landing point at the descending aortic straight segment is recommended.