In January 2025, the i-dot-ai/redbox repo delivered targeted instrumentation improvements for ChatMessage metrics to enable user-level analytics and richer feedback insights, along with a critical data-model alignment fix. We reintroduced the user_id field in elastic metrics logging for ChatMessage to support user-level analytics and debugging; added new logging fields to capture chat-level feedback metrics and the number of selected files, enabling visibility into user engagement and work efficiency; and fixed and standardized the counting of selected files in ChatMessage by using the proper count() on the ManyToMany relationship and updating the related model references. These changes improve business value by enabling granular analytics, reducing debugging time, and laying groundwork for data-driven optimization, while keeping changes scoped and risk-minimized.