Background: We have employed a conservative management approach, including intensive control of both blood pressure and heart rate, in patients with aortic intramural hematoma (AIMH) and retrograde thrombosed type A acute aortic dissection (RT-TAAAD), sharing common clinical and imaging characteristics. Methods: To evaluate the outcomes of our conservative management approach, we retrospectively reviewed the clinical records of 98 patients diagnosed with AIMH or RT-TAAAD from January 2008 to March 2023. A conservative management approach was applied, except for those patients with an aortic diameter ≥ 55 mm, false lumen expansion, or cardiac tamponade, who underwent emergency aortic repair. Results: Besides 2 patients, who declined surgery and subsequently died from aortic rupture, 18 patients underwent urgent aortic surgery, while 78 did not. Multivariable logistic regression analysis identified the extrusion type of ulcer-like projections (ULPs) on admission and a maximum aortic diameter ≥ 45 mm on Day 1 as risk factors for acute aortic surgery. Among the 78 patients who were discharged, 9 (12%) underwent aortic surgery, while 69 (88%) did not, with a median follow-up of 44 months. The overall actuarial aortic surgery-free rates were 78% at 1 year and 72% at 5 years, respectively. A Cox proportional hazards analysis identified ULPs and an aortic diameter ≥ 45 mm at discharge as risk factors for late aortic surgery. Conclusions: The early and late outcomes of our conservative strategy for AIMH and RT-TAAAD demonstrate favorable surgery-free rates. The extrusion type of ULPs on admission and an aortic diameter ≥ 45 mm on Day 1 are predictors of acute aortic surgery, while ULPs and an aortic diameter ≥ 45 mm at discharge are predictors of late surgery.