Technology change management in large financial institutions depends on risk assessments that are accurate, consistent, and auditable. In practice, many institutions still rely on self-reported questionnaires. Those questionnaires are subjective, easy to game, and poor at separating routine changes from the ones that later trigger major incidents. This paper presents SENTRY, a risk assessment platform that replaces questionnaire-based scoring with a deterministic machine learning pipeline built from gradient-boosted decision trees (XGBoost) and hybrid retrieval-augmented generation (RAG). The system combines structured operational metadata, application dependency graphs, and historical incident records with a hybrid semantic and lexical search over historical change requests. The retrieval step captures the risk signal in unstructured change request text, then compresses that signal into a single scalar feature before model inference. That design keeps the model deterministic and preserves per-prediction explainability via SHAP values. Evaluated on enterprise-scale change data, SENTRY achieves a ROC AUC of 0.87 and 85% overall accuracy, and it detects high-risk changes at roughly 3.25 times the rate of the existing process. We close by examining the architectural trade-offs behind this design and what they imply for the use of machine learning in regulated change management.

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