Background: Thoracic endovascular aortic repair (TEVAR) is the preferred treatment for complicated type B aortic dissections. Late complications, particularly in chronic dissections, may combine multiple mechanisms such as proximal type I endoleak, false lumen progression, and true lumen compression, posing significant risks for rupture and malperfusion. Case presentation: We report the case of a 62‑year‑old man with a history of TEVAR for ruptured thoracic aneurysm secondary to chronic type B dissection. One year later, he presented with persistent thoracic pain. Computed tomography angiography (CTA) revealed a proximal type IA endoleak, false lumen progression with distal re‑entry, and marked true lumen compression in the descending thoracic and abdominal aorta. The left renal artery originated from the false lumen. The multidisciplinary team opted for distal stent graft extension to exclude distal re‑entries, depressurise the false lumen, and restore true lumen calibre. Discussion: This case illustrates the interplay between persistent proximal endoleak, distal re‑entries, and false lumen pressurisation leading to adverse remodelling. True lumen compression is a key driver of malperfusion risk and reduced repair durability. Distal extension directly addresses both the haemodynamic and mechanical components of the complication. This approach aligns with the 2024 European Society of Cardiology (ESC) Guidelines, which recommend early reintervention for type I endoleaks in chronic dissections, particularly when associated with false lumen perfusion or malperfusion. Conclusion: Late combined complications after TEVAR require tailored, anatomy‑driven strategies. Distal extension can effectively treat proximal endoleak, false lumen progression, and true lumen compression in a single intervention, improving long‑term aortic stability and patient outcomes.