Valid JSON did not stop my agent from missing a deadline or posting an update twice. The fix was to separate three jobs: constrain the agent’s proposed action, make repeated side-effect requests safe where the destination API supports it, and track deadlines and completion in durable application state.
Why a retry can create a duplicate
Suppose an agent asks a service to post an update. The service creates the post, but the response times out before the agent receives confirmation. If the agent blindly retries, the same update may be created again. From the caller’s point of view, a timeout does not prove the first request failed.
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These are separate failure modes, so they need separate controls. A structured response can make the proposed action easier to parse and validate. An idempotency mechanism can let a destination recognize a repeated operation. Neither one schedules work or guarantees that it finishes before a deadline.
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Use JSON Schema to constrain the proposed action
Have the model return a defined object—such as an action type, destination, content, and due time—instead of asking it to execute an external side effect directly. Validate the response in your application, then check authorization and whether the action is due before dispatching it.
OpenAI distinguishes JSON mode, which produces valid JSON, from Structured Outputs, which is designed to adhere to a supplied JSON Schema. That contract helps catch missing or incorrectly typed fields, but it is not an execution guarantee: applications still need to handle refusals and incomplete output. See OpenAI’s Structured Outputs documentation.
Give each intended side effect a stable identity
Before sending an action, persist an operation record with a stable ID and its intended payload. If an attempt must be retried, reuse that identity and the same operation details rather than creating a fresh operation for what is logically the same post.
Whether this prevents duplicates depends on the receiving API’s contract. For example, Google Chat’s spaces.messages.create method accepts an optional requestId. Google says repeated identical requests with the same ID create one message and subsequent requests return the existing message. Its guidance also requires identical request content and the same authentication credentials. This is an endpoint-specific example, not a universal rule for APIs; the documentation does not establish a universal retention period for IDs. See Google Chat’s message-create method.
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Track deadlines in durable state
Store the due timestamp and an overall operation deadline with the task, then use a durable scheduler or worker to find and execute due work. Persist the operation’s status and result so they survive a process restart; do not rely on a model response or an in-memory timer as the only record that a task exists.
Distinguish an individual attempt timeout from the end-to-end deadline. An attempt can time out while the overall task still has time for a bounded retry. Once the deadline or retry budget is exhausted, stop or defer attempts, record the failure, and expose a recoverable state rather than silently dropping the task.
Bound retries and make them observable
Choose which errors are retryable, cap the number or duration of retries, and use backoff rather than sending requests continuously. Google recommends logging failures and exponential backoff for time-based, quota, and network errors. OpenAI says its official SDKs retry eligible 429 and 503 responses subject to settings; an attempt timeout is not necessarily the deadline for the whole operation. See Google’s webhook guidance and OpenAI’s retry guidance.
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Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Account for the destination’s delivery limits
Google Chat incoming webhooks are asynchronous, one-way notifications: they cannot receive or respond to user messages. Google’s webhook guide documents a quota of one request per second per space, shared among that space’s webhooks. A workflow that uses them must account for that rate and should not treat the webhook response as a complete message or proof of downstream handling. Check the current Google Chat webhook documentation for the applicable behavior and limits.
A practical execution sequence
- Generate: Ask the model for a structured action matching a schema; handle refusal, incomplete output, and invalid data.
- Validate: Check the action’s fields, authorization, destination, and due time in application code.
- Persist: Save the task, stable operation identity, payload, due timestamp, overall deadline, and status before dispatch.
- Execute: Send the action using the destination’s idempotency feature when available, following its exact identity, payload, and authentication rules.
- Record: Persist the result and update task status. On retry, reuse the same operation identity and apply bounded backoff.
- Recover: If attempts or the deadline are exhausted, log and surface a recoverable failure instead of retrying indefinitely or marking it complete.
What to check when choosing an implementation
- Output contract: Does the model response merely parse as JSON, or does it adhere to a schema? How are refusals and incomplete output handled?
- Deduplication contract: Does the destination accept an idempotency key? What are its scope and reuse rules, and must payload and credentials remain identical?
- Durability: Do due times and completion records survive worker or process restarts?
- Retry and deadline policy: Which failures are retried, with what backoff and attempt limit, and what ends the overall operation?
- Observability: Can logs connect attempts to one operation and distinguish a confirmed failure from an ambiguous timeout?
If the destination has no server-side idempotency feature, your application can record operation identities and results, but a local record cannot eliminate every race between a remote side effect succeeding and the local system saving that success. Treat that as a design limitation, not an exactly-once guarantee.
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