LLM agents often fail mid-task due to invalid tool calls, repeated actions, or poorly grounded reasoning, and learning from these failures is a path to reliability.
We find that how failure knowledge reaches the agent matters as much as what it contains.
Failure lessons are conditional: kept in the agent's context, they misfire when their failure is absent, and removing them from an evolving playbook improves performance.
Runtime interventions, in contrast, act only when a failure occurs but do not learn from their repairs.
We argue that failure knowledge is conditional knowledge and should be conditionally exposed, and instantiate this principle in Sentry, a failure-management layer that runs alongside the agent.
When Sentry detects a failure, it retrieves matching lessons from an external playbook to guide recovery, verifies without access to task rewards whether the agent recovered, and stores a new lesson only if it did; the full playbook never enters the agent's context.
Across multiple agentic benchmarks, Sentry outperforms the strongest runtime-intervention baseline on every benchmark, by 37% on average, and the strongest context-evolution baseline by 39% on the two benchmarks where both are evaluated; combining Sentry with context evolution yields further gains.
Learned lessons transfer to held-out tasks, and controlled experiments show that exposing the full playbook to the agent lowers performance even when relevant lessons remain available on demand.