Objective: This study aimed to analyze the outcomes and challenges associated with surgical redo procedures following aortic valve replacement for acute infective endocarditis. While transcatheter aortic valve implantation is growing in terms of its utilization for degenerative bioprostheses failure, valve-in-valve procedures are limited in acute aortic endocarditis. Surgical interventions for aortic prosthesis endocarditis carry a significant risk, with a higher mortality and morbidity, often requiring concomitant complex procedures. Methods: This was a retrospective, monocentric, observational study. We identified 352 patients with infective endocarditis from the institutional database. After applying the inclusion and exclusion criteria, 54 patients who underwent surgical re-operation between 2016 and 2023 were included. Endpoints included early and late mortality, complications, and major adverse cardiac and cerebrovascular events (MACCEs). Results: From the cohort, predominantly male and with an average age of 71.9 ± 12.1 years old (79.6%), the following notable findings were derived: isolated aortic valve replacement was feasible only in 34 patients (63%) while more complex procedures were demanded in the other cases; the overall 30-day mortality rate was 18.5%, post-operative ECMO occurred in 9.3% of cases, and post-operative new stroke in 2.7%; the 5-year overall survival rate was 58.3 ± 18.6%, while freedom from MACCEs was 41.7 ± 19.7%. Another re-intervention was required in three patients during follow-up, with one case attributed to re-endocarditis. Conclusions: Despite advancements in surgical and perioperative care, redo procedures for acute infective endocarditis pose significant risks, as evidenced by the high 30-day mortality rate. However, the 5-year survival suggests a relatively acceptable outcome, underscoring the complexities and challenges inherent in managing this condition surgically.