During October 2024, Costa enhanced TLS handshake observability in the Shopify/grpc repository by developing a feature that improves error reporting for certificate verification failures. Using C++ and leveraging skills in debugging and network security, Costa implemented detailed diagnostics that capture and report the specific reason for certificate verification issues during TLS handshakes. This approach enables more actionable telemetry and supports faster triage by providing precise diagnostic information to callers. The work focused on error handling within secure network communications, reducing the mean time to detect and resolve TLS-related problems and strengthening the reliability and security posture of the codebase.