Unmanned Traffic Management (UTM) systems are cloud-based platforms designed to manage and coordinate multiple aerial vehicles remotely. UTM systems are safety-critical which cannot tolerate failures like crash or collision. To reveal latent vulnerabilities, there are neither optimal failure-exposing demonstrations nor clear reward signals. Additionally, UTM's self-healing capability introduces the ``long-tail effect'' of critical failures. We propose framing UTM vulnerability discovery as a sequence modeling problem amenable to transformer-based RL architectures. Our approach leverages attention mechanisms to directly model the relationship among system states, and predict optimal actions. Our framework introduces a Policy Model that generates targeted test scenarios and an Action Sampler that enforces domain constraints. We use a risk-based reward function to guide exploration. Through extensive evaluation on a 700-hour simulation study, we demonstrate an 8 improvement in vulnerability discovery efficiency compared to expert-guided testing. It also discovers critical edge cases that traditional methods have missed.