0004 Required idempotency

Context

Agents and integrators retry. A network error on a send is ambiguous: the request may or may not have reached the service, and the service’s call to the transport may or may not have reached the provider. Pylota’s experience before this product: a failed send re-ran an LLM turn and produced a second email (PRD section 2). A duplicate email to a customer is worse than a delayed one.

Facts that constrain the design (Cloudflare Email Sending docs, read 2026-10-09): the structured send() returns a messageId; Message-ID, Date and DKIM headers are set by the platform and cannot be set by the caller, so the provider cannot deduplicate on a client-chosen Message-ID. A transport timeout or a dropped connection after the request was written leaves the outcome unknown.

Decision

1. Idempotency-Key is required on POST …/messages, …/reply, …/reply-all and …/forward (1–255 printable ASCII characters). A missing key is 400 idempotency_key_required. MCP send tools require an idempotency_key argument. The key is optional on every other POST.
2. Reservation in the mailbox transaction. The mailbox stores the key with a fingerprint (sha256(operation, target, canonical body)) in the same transaction that stores the message as queued. Keys are kept for 30 days, scoped per identity for mail and per tenant for other POSTs.
3. Replays. Same key and same request: the original response, with "deduplicated": true and the header Idempotent-Replayed: true. Same key, different request: 409 idempotency_conflict. Same key while the first request is running: 409 request_in_progress (retryable).
4. Uncertain is a state, not a retry. A transport outcome that cannot be known becomes uncertain and is never resent automatically. Definitely-not-sent outcomes (validation, quota, rate limits) may be retried by the queue.
5. Reconciliation. Uncertain sends are matched to provider events by sender, recipient and subject within 30 minutes; a match moves the message to its real status with reconciled: true and emits message.reconciled (FR-DLV-4).
6. Human resolution. POST …/messages/{id}/resolve {"outcome": "sent" | "not_sent"}. not_sent marks the message failed (resolved_not_sent); a new send needs a new key.

Consequences

• Every retry of the same message, by any client, after any failure, returns the same result: zero duplicate sends attributed to retries (PRD success metric).
• Clients must generate a key per logical message and keep it across retries. The SDK exposes .idempotency_key(…); agent guides tell agents to derive it from their own task identifiers.
• After 30 days a key is forgotten and its reuse is a new send; this is documented.
• Some sends end uncertain and need reconciliation or a human. That is the price of never guessing.
• The mailbox stores a response per key for 30 days, which is counted in the privacy inventory.

Alternatives considered

• Optional keys. Lower friction for simple callers. Rejected: the callers most likely to retry blindly (LLM agents, generic HTTP tooling) are the least likely to send a key, and one forgotten key is one duplicate email.
• Automatic retry of uncertain sends. Fewer messages stuck in uncertain. Rejected: when the first attempt did reach the provider, the retry sends a second email; the provider offers no client-controlled deduplication to make that safe.
• Deriving the key from a hash of the body. No client work. Rejected: two legitimate identical messages (a reminder sent twice on purpose) would be merged, and a corrected retry with a small change would send twice.
• Deduplicating on Message-ID at the provider. The usual SMTP-era answer. Not available: Email Sending sets Message-ID itself.