At a recent Gartner event, discussions highlighted the pervasive challenges faced by companies during system migrations, characterized by complex tech stacks, undocumented business logic, and legacy systems tied together with fragile scripts. The unique difficulties of each migration, particularly the unpredictable edge cases, often immobilize companies, leaving them reliant on outdated systems despite having cloud contracts. Traditional automation and rule-based solutions have reached their limits, unable to address the myriad of edge cases effectively. The proposed solution is to employ large language models (LLMs) that can better manage the intricate dependencies and variations inherent in real-world migrations, offering a more adaptable approach to overcoming these challenges.