@tetral-ai/sdk 0.110.0-alpha.1

package/src/lib/tools/SessionToolRunner.ts

@@ -0,0 +1,616 @@
+import { AnthropicError } from '../../core/error';
+import type { Anthropic } from '../../client';
+import type {
+  BetaManagedAgentsAgentCustomToolUseEvent,
+  BetaManagedAgentsAgentToolUseEvent,
+  BetaManagedAgentsSessionEvent,
+  BetaManagedAgentsStreamSessionEvents,
+  BetaManagedAgentsUserCustomToolResultEventParams,
+  BetaManagedAgentsUserToolResultEventParams,
+} from '../../resources/beta/sessions/events';
+import type { BetaToolResultContentBlockParam } from '../../resources/beta';
+import { loggerFor, type Logger } from '../../internal/utils/log';
+import { sleep } from '../../internal/utils/sleep';
+import { isFatal4xx } from '../../internal/utils/backoff';
+import { linkAbort } from '../../internal/utils/abort';
+import { AsyncQueue } from '../../internal/utils/async-queue';
+import { buildHeaders } from '../../internal/headers';
+import { helperHeader } from '../../internal/stainless-helper-header';
+import type { RequestOptions } from '../../internal/request-options';
+import { runRunnableTool, toolName, type BetaRunnableTool } from './BetaRunnableTool';
+import type { BetaToolRunnerRequestOptions } from './BetaToolRunner';
+
+/** Beta header for the managed-agents API. */
+export const MANAGED_AGENTS_BETA = 'managed-agents-2026-04-01';
+
+const STREAM_BACKOFF_START_MS = 500;
+const STREAM_BACKOFF_CAP_MS = 10_000;
+const TOOL_TIMEOUT_MS = 120_000;
+const DRAIN_TIMEOUT_MS = 30_000;
+const SEND_RETRIES = 3;
+
+/** Block type accepted in a `user.tool_result` event's content — codegen'd, stays in sync with the API. */
+type SessionContentBlock = NonNullable<BetaManagedAgentsUserToolResultEventParams['content']>[number];
+
+/**
+ * A tool-call event the runner dispatches against the local registry: either a
+ * builtin `agent.tool_use` (answered with `user.tool_result`) or a custom
+ * `agent.custom_tool_use` (answered with `user.custom_tool_result`). Server-side
+ * `agent.mcp_tool_use` calls are intentionally excluded — the runner does not
+ * handle them.
+ */
+type DispatchedToolUseEvent = BetaManagedAgentsAgentToolUseEvent | BetaManagedAgentsAgentCustomToolUseEvent;
+
+/**
+ * The result-event params paired with a {@link DispatchedToolUseEvent}: a
+ * `user.tool_result` answers an `agent.tool_use`, a `user.custom_tool_result`
+ * answers an `agent.custom_tool_use`. The two pairs must be matched exactly.
+ */
+type DispatchedToolResultParams =
+  | BetaManagedAgentsUserToolResultEventParams
+  | BetaManagedAgentsUserCustomToolResultEventParams;
+
+export interface SessionToolRunnerOptions {
+  client: Anthropic;
+  /**
+   * Tools to expose to the session, in the same {@link BetaRunnableTool} shape
+   * `client.beta.messages.toolRunner` accepts. Use
+   * `betaAgentToolset20260401({ workdir })` from
+   * `@tetral-ai/sdk/tools/agent-toolset/node` for the standard
+   * `agent_toolset_20260401` set; filter or extend the array to customise.
+   */
+  tools: Array<BetaRunnableTool>;
+  /**
+   * Once the session goes idle with `stop_reason.type === "end_turn"`, the
+   * runner keeps running for this many milliseconds before stopping; any new
+   * event resets the countdown and it re-arms on the next `end_turn` idle.
+   * Defaults to {@link DEFAULT_MAX_IDLE_MS} (60s). `0` (or negative) disables
+   * it — the runner then only stops on session termination or the consumer
+   * breaking out / aborting.
+   */
+  maxIdleMs?: number;
+  /** External abort signal. Aborting it ends the iteration. */
+  signal?: AbortSignal;
+  /**
+   * Extra per-request options merged into every call this runner issues
+   * (event stream / list / send). Mirrors what `client.beta.messages.toolRunner`
+   * accepts: custom `headers` (e.g. a proxy's auth/routing headers) reach the
+   * poll/heartbeat/stop/stream/list/send calls. The runner always owns the abort
+   * signal, so a `signal` here is ignored — pass {@link SessionToolRunnerOptions.signal}
+   * to abort externally.
+   */
+  requestOptions?: BetaToolRunnerRequestOptions;
+}
+
+/** Default {@link SessionToolRunnerOptions.maxIdleMs}: 60 seconds. */
+export const DEFAULT_MAX_IDLE_MS = 60_000;
+
+/**
+ * Outcome of a single tool execution dispatched by {@link SessionToolRunner}.
+ *
+ * Yielded after the tool ran (or failed) and after the result was posted back
+ * to the session as a `user.tool_result` event. Consumers can read either the
+ * embedded {@link DispatchedToolCall.event} / {@link DispatchedToolCall.result}
+ * blocks or the flat top-level convenience fields.
+ */
+export interface DispatchedToolCall {
+  /**
+   * The `agent.tool_use` or `agent.custom_tool_use` event that triggered this
+   * dispatch. Read `event.input` for the raw tool input and `event.name` for the
+   * tool name; `event.type` distinguishes a builtin tool call from a custom one.
+   */
+  readonly event: DispatchedToolUseEvent;
+  /**
+   * The result event posted (or attempted) back to the session for this call: a
+   * `user.tool_result` for an `agent.tool_use`, a `user.custom_tool_result` for
+   * an `agent.custom_tool_use`. Read `result.content` for the tool's output
+   * blocks and `result.is_error` for the error flag.
+   *
+   * `undefined` when no result event was ever built — i.e. the tool name is
+   * not one this runner owns and, under the split-client behavior, it
+   * deliberately posted nothing and left the id pending for its owner.
+   */
+  readonly result?: DispatchedToolResultParams;
+  /**
+   * Flat convenience for `event.id` — the id of the tool-use event this result
+   * answers (echoed back as `tool_use_id` / `custom_tool_use_id` on the result).
+   */
+  readonly toolUseId: string;
+  /** Flat convenience for `event.name` — the dispatched tool's name. */
+  readonly name: string;
+  /**
+   * Flat convenience for `result.is_error` — `true` when the tool threw,
+   * `false` on success and for a skipped unowned call.
+   */
+  readonly isError: boolean;
+  /**
+   * Whether a result event for this call reached the session. `false` when the
+   * post itself failed (typically a permanent 4xx or send-retry exhaustion)
+   * including Tetral Cloud-hosted rejection of client-supplied
+   * `user.tool_result` / `user.custom_tool_result` variants. Treat this as an
+   * explicit local failure state, not as a successful tool-result delivery.
+   *
+   * Also `false` — with no `result` event ever built — for a tool name this
+   * runner does not own when it deliberately posts nothing and leaves the id
+   * pending for its owner (the split-client behavior).
+   */
+  readonly posted: boolean;
+}
+
+/** Returns true if `ev` is a `session.status_idle` with `stop_reason` `end_turn`. */
+function isEndTurnIdle(ev: { type?: string; stop_reason?: { type?: string } }): boolean {
+  return ev.type === 'session.status_idle' && ev.stop_reason?.type === 'end_turn';
+}
+
+/**
+ * The sessions-side counterpart to `client.beta.messages.toolRunner`: an
+ * async-iterable that attaches to a managed-agents session, executes every
+ * incoming `agent.tool_use` and `agent.custom_tool_use` event against a local
+ * tool registry, posts the matching result back (`user.tool_result` for the
+ * former, `user.custom_tool_result` for the latter), and yields one
+ * {@link DispatchedToolCall} per completed call. Server-side `agent.mcp_tool_use`
+ * calls are not dispatched. Internally drives event-stream reconnect and result
+ * posting.
+ *
+ * Iteration ends when the session terminates (`session.status_terminated` /
+ * `session.deleted`), when the consumer `break`s out of the loop or aborts the
+ * supplied signal, or — once the session has gone idle with
+ * `stop_reason.type === "end_turn"` — when `maxIdleMs` elapses with no new
+ * event (any new event resets that countdown; it re-arms on the next `end_turn`
+ * idle; `maxIdleMs <= 0` disables it). The `finally` branch drains any in-flight
+ * tool calls and runs each tool's `close()` cleanup hook. It does *not* touch
+ * the work-item lease — wrap it in an `EnvironmentWorker` if you need
+ * heartbeating / force-stop.
+ *
+ * Tetral Cloud-hosted runtime rejects client-supplied tool-result event
+ * variants in this stage. When such a post is rejected, yielded calls have
+ * `posted: false`; consumers must not treat that as hosted-runtime success.
+ *
+ * @example
+ * ```ts
+ * import { betaAgentToolset20260401 } from '@tetral-ai/sdk/tools/agent-toolset/node';
+ *
+ * for await (const call of client.beta.sessions.events.toolRunner(work.data.id, {
+ *   tools: [...betaAgentToolset20260401({ workdir }), myTool],
+ * })) {
+ *   console.log(`${call.name} -> ${call.isError ? 'error' : 'ok'}`);
+ * }
+ * ```
+ */
+export class SessionToolRunner implements AsyncIterable<DispatchedToolCall> {
+  readonly client: Anthropic;
+  readonly sessionId: string;
+  readonly tools: ReadonlyArray<BetaRunnableTool>;
+  readonly maxIdleMs: number;
+
+  #consumed = false;
+  readonly #controller: AbortController;
+  readonly #detachExternal: () => void;
+  readonly #requestOpts: BetaToolRunnerRequestOptions | undefined;
+  readonly #toolByName: Map<string, BetaRunnableTool>;
+  readonly #logger: Logger;
+  readonly #seen = new Set<string>();
+  readonly #answered = new Set<string>();
+  readonly #results = new AsyncQueue<DispatchedToolCall>();
+  #inFlightCount = 0;
+  #onIdle: (() => void) | null = null;
+  // When the session is idle past an `end_turn`, the pending stop timer; cleared
+  // by any new event. Event-driven — there is no polling watchdog.
+  #idleTimer: ReturnType<typeof setTimeout> | undefined;
+
+  constructor(sessionId: string, opts: SessionToolRunnerOptions) {
+    this.client = opts.client;
+    this.sessionId = sessionId;
+    this.tools = opts.tools;
+    this.maxIdleMs = opts.maxIdleMs ?? DEFAULT_MAX_IDLE_MS;
+    this.#logger = loggerFor(opts.client);
+    this.#toolByName = new Map(opts.tools.map((t) => [toolName(t), t]));
+    this.#controller = new AbortController();
+    this.#detachExternal = linkAbort(opts.signal, this.#controller);
+    this.#requestOpts = opts.requestOptions;
+  }
+
+  /** Read-only view of this runner's abort signal. */
+  get signal(): AbortSignal {
+    return this.#controller.signal;
+  }
+
+  /** Abort the runner. Background tasks will wind down and `for await` will exit cleanly. */
+  abort(): void {
+    this.#controller.abort();
+  }
+
+  async *[Symbol.asyncIterator](): AsyncIterator<DispatchedToolCall> {
+    if (this.#consumed) {
+      throw new AnthropicError('Cannot iterate over a consumed SessionToolRunner');
+    }
+    this.#consumed = true;
+    this.#logger.info('session tool runner starting', {
+      component: 'session-tool-runner',
+      session_id: this.sessionId,
+    });
+
+    // The one background promise: drives the event stream and dispatches tools.
+    // Its `.catch` aborts the controller so the main loop unwinds.
+    const streamPromise = this.#streamLoop().catch((e) => {
+      if (!this.#controller.signal.aborted) {
+        this.#logger.error('stream loop failed', { error: String(e) });
+      }
+      this.#controller.abort();
+    });
+
+    try {
+      // Phase 1: yield results as they arrive. `next(signal)` resolves
+      // `done: true` when the controller aborts — cancellation is handled in
+      // the queue read, no outer `Promise.race` needed.
+      while (true) {
+        const next = await this.#results.next(this.#controller.signal);
+        if (next.done) break;
+        yield next.value;
+      }
+
+      // Phase 2: let the stream loop settle (and push any final results), then
+      // drain whatever is still queued before closing.
+      await streamPromise;
+      let pending: DispatchedToolCall | undefined;
+      while ((pending = this.#results.tryShift()) !== undefined) {
+        yield pending;
+      }
+    } finally {
+      this.#controller.abort();
+      this.#disarmIdleTimer();
+      // Re-await defensively in case the consumer broke out of phase 1 before
+      // phase 2 ran — a no-op if it already settled.
+      await streamPromise;
+      try {
+        await this.#drain();
+      } catch (e) {
+        this.#logger.warn('drain failed', { error: String(e) });
+      }
+      this.#results.close();
+      for (const t of this.tools) {
+        try {
+          // `close` is typed `() => Promisable<void>`, so a single `await`
+          // covers both the sync and async return.
+          await t.close?.();
+        } catch (e) {
+          this.#logger.warn('tool.close failed', { tool: toolName(t), error: String(e) });
+        }
+      }
+      // Detach from the external signal so the consumer can drop their signal
+      // reference without leaking this iterator instance.
+      this.#detachExternal();
+    }
+  }
+
+  // ===== request options =====
+
+  /**
+   * Request options for every helper-issued call: the caller's `requestOptions`
+   * (custom proxy headers etc.) with the helper telemetry header stamped on and
+   * the runner's own abort signal forced last so it always owns cancellation.
+   */
+  #requestOptions(): RequestOptions {
+    return {
+      ...this.#requestOpts,
+      headers: buildHeaders([helperHeader('session-tool-runner'), this.#requestOpts?.headers]),
+      signal: this.#controller.signal,
+    };
+  }
+
+  // ===== event stream =====
+
+  async #streamLoop(): Promise<void> {
+    const ctrl = this.#controller;
+    let backoff = STREAM_BACKOFF_START_MS;
+    while (!ctrl.signal.aborted) {
+      try {
+        // Establish the event stream *before* reconciling history, so an event
+        // emitted in the gap between listing and attaching is buffered on the
+        // stream rather than lost. `seen`/`answered` dedup any event that shows
+        // up both in the reconcile pass and on the live stream.
+        const stream = await this.client.beta.sessions.events.stream(
+          this.sessionId,
+          {},
+          this.#requestOptions(),
+        );
+        await this.#reconcile();
+        for await (const ev of stream) {
+          backoff = STREAM_BACKOFF_START_MS;
+          if (await this.#handleStreamEvent(ev)) return;
+        }
+      } catch (e) {
+        // An abort throws to unwind the caller (the iterator's `streamPromise`
+        // `.catch`) rather than returning early and letting it carry on.
+        ctrl.signal.throwIfAborted();
+        if (isFatal4xx(e)) {
+          this.#logger.error('permanent stream failure, shutting down', { error: String(e) });
+          ctrl.abort();
+          throw e;
+        }
+        this.#logger.warn('stream disconnected, reconnecting', {
+          error: String(e),
+          backoff_ms: backoff,
+        });
+      }
+      ctrl.signal.throwIfAborted();
+      await sleep(backoff, ctrl.signal);
+      backoff = Math.min(backoff * 2, STREAM_BACKOFF_CAP_MS);
+    }
+  }
+
+  /**
+   * Read full history before dispatching so a `tool_use` whose result appears
+   * later in the same history is not re-executed. Runs after the live stream is
+   * already attached (see {@link SessionToolRunner.#streamLoop}).
+   */
+  async #reconcile(): Promise<void> {
+    const ctrl = this.#controller;
+    const pending: DispatchedToolUseEvent[] = [];
+    let lastWasEndTurn = false;
+    try {
+      for await (const ev of this.client.beta.sessions.events.list(
+        this.sessionId,
+        { limit: 1000 },
+        this.#requestOptions(),
+      )) {
+        this.#ingestHistory(ev, pending);
+        lastWasEndTurn = isEndTurnIdle(ev);
+      }
+    } catch (e) {
+      // An abort throws to unwind the caller; a real list failure is
+      // non-fatal — undo the speculative `seen` entries and let `#streamLoop`
+      // carry on with the live stream.
+      ctrl.signal.throwIfAborted();
+      this.#logger.warn('reconcile list failed', { error: String(e) });
+      // If list itself failed, undo the speculative `seen` entries so the next
+      // reconcile pass (or the live stream) can pick them up. Leave the idle
+      // timer untouched — the history we read may be incomplete.
+      for (const ev of pending) this.#seen.delete(ev.id);
+      return;
+    }
+    const unanswered = pending.filter((ev) => !this.#answered.has(ev.id));
+    // If the most recent event in history is an `end_turn` idle and there's no
+    // outstanding tool work, the session is done — arm the idle timer so the
+    // runner stops even if that `end_turn` arrived during a disconnect.
+    if (lastWasEndTurn && unanswered.length === 0) this.#armIdleTimer();
+    else this.#disarmIdleTimer();
+    for (const ev of unanswered) await this.#execute(ev);
+  }
+
+  #ingestHistory(ev: BetaManagedAgentsSessionEvent, pending: DispatchedToolUseEvent[]): void {
+    if (ev.type === 'agent.tool_use' || ev.type === 'agent.custom_tool_use') {
+      // Mark the event seen so a replay on the live stream is not dispatched
+      // twice, but decide whether it still needs executing from `answered`, not
+      // `seen`: a call whose result post failed is seen-but-unanswered, and must
+      // be retried on the next reconcile pass rather than silently dropped.
+      this.#seen.add(ev.id);
+      if (!this.#answered.has(ev.id)) pending.push(ev);
+    } else if (ev.type === 'user.tool_result') {
+      this.#answered.add(ev.tool_use_id);
+    } else if (ev.type === 'user.custom_tool_result') {
+      this.#answered.add(ev.custom_tool_use_id);
+    }
+  }
+
+  /** Returns true when the runner should exit. */
+  async #handleStreamEvent(ev: BetaManagedAgentsStreamSessionEvents): Promise<boolean> {
+    // Arm/disarm the idle timer: an `end_turn` idle starts the grace countdown;
+    // any other event cancels it.
+    if (isEndTurnIdle(ev)) this.#armIdleTimer();
+    else this.#disarmIdleTimer();
+    switch (ev.type) {
+      case 'agent.tool_use':
+      case 'agent.custom_tool_use':
+        if (!this.#seen.has(ev.id)) {
+          this.#seen.add(ev.id);
+          await this.#execute(ev);
+        }
+        return false;
+      case 'user.tool_result':
+        this.#answered.add(ev.tool_use_id);
+        return false;
+      case 'user.custom_tool_result':
+        this.#answered.add(ev.custom_tool_use_id);
+        return false;
+      case 'session.status_terminated':
+      case 'session.deleted':
+        this.#logger.info('session terminated', {
+          component: 'session-tool-runner',
+          session_id: this.sessionId,
+        });
+        this.#controller.abort();
+        return true;
+      default:
+        return false;
+    }
+  }
+
+  // ===== idle timer =====
+
+  /** (Re)start the grace countdown that stops the runner after `maxIdleMs` of idle. */
+  #armIdleTimer(): void {
+    this.#disarmIdleTimer();
+    if (this.maxIdleMs <= 0) return;
+    this.#idleTimer = setTimeout(() => {
+      this.#logger.info('session idle after end_turn; stopping', {
+        component: 'session-tool-runner',
+        session_id: this.sessionId,
+        max_idle_ms: this.maxIdleMs,
+      });
+      this.#controller.abort();
+    }, this.maxIdleMs);
+  }
+
+  /** Cancel a pending idle countdown, if any. */
+  #disarmIdleTimer(): void {
+    if (this.#idleTimer !== undefined) {
+      clearTimeout(this.#idleTimer);
+      this.#idleTimer = undefined;
+    }
+  }
+
+  // ===== tool execution =====
+
+  async #execute(ev: DispatchedToolUseEvent): Promise<void> {
+    if (this.#answered.has(ev.id)) return;
+    this.#logger.info('executing tool', {
+      component: 'session-tool-runner',
+      session_id: this.sessionId,
+      tool: ev.name,
+      tool_use_id: ev.id,
+    });
+    this.#inFlightCount++;
+    try {
+      const tool = this.#toolByName.get(ev.name);
+      if (!tool) {
+        // Skip (split-client partial fulfilment): a name this runner
+        // is not registered for belongs to the other client servicing this
+        // session (typically the customer's app backend handling custom tools).
+        // Post NO result, do not mark it answered, and leave the tool_use_id
+        // pending for its owner — claiming it would corrupt the conversation.
+        // Still yield the call so the consumer can observe the unowned
+        // dispatch; nothing was sent, so `posted`/`isError` stay false and no
+        // `result` event is populated. The id stays unanswered, so reconcile
+        // keeps it out of the idle/end-turn accounting and re-surfaces it after
+        // a reconnect until its owner answers it.
+        this.#logger.info('tool not owned by this runner; leaving the tool_use_id pending for its owner', {
+          component: 'session-tool-runner',
+          session_id: this.sessionId,
+          tool: ev.name,
+          tool_use_id: ev.id,
+        });
+        this.#results.push({ event: ev, toolUseId: ev.id, name: ev.name, isError: false, posted: false });
+        return;
+      }
+      let content: string | Array<BetaToolResultContentBlockParam>;
+      let isError: boolean;
+      // Per-tool controller: aborts on the runner's own signal *or* the
+      // per-tool timeout, so an in-flight tool stops promptly when the runner
+      // is aborted instead of running until the timeout.
+      const toolCtrl = new AbortController();
+      const detachTool = linkAbort(this.#controller.signal, toolCtrl);
+      const timer = setTimeout(() => toolCtrl.abort(), TOOL_TIMEOUT_MS);
+      try {
+        // Pass the source `agent.tool_use` / `agent.custom_tool_use` event
+        // straight through as the run context's `toolUse` — it is a union
+        // member of `BetaToolUse`, no Messages-block adapter needed.
+        const outcome = await runRunnableTool(tool, ev.input, {
+          toolUse: ev,
+          toolUseBlock: ev,
+          signal: toolCtrl.signal,
+        });
+        content = outcome.content;
+        isError = outcome.isError;
+      } finally {
+        clearTimeout(timer);
+        detachTool();
+      }
+      // Answer with the result event that matches the call kind: a
+      // `user.tool_result` for an `agent.tool_use`, a `user.custom_tool_result`
+      // for an `agent.custom_tool_use`. Posting the wrong one leaves the call
+      // unanswered and the session stuck.
+      const result = buildResultEvent(ev, isError, toSessionContent(content));
+      const posted = await this.#sendResult(result, ev.id);
+      this.#results.push({
+        event: ev,
+        result,
+        toolUseId: ev.id,
+        name: ev.name,
+        isError,
+        posted,
+      });
+    } finally {
+      this.#inFlightCount--;
+      if (this.#inFlightCount === 0) this.#onIdle?.();
+    }
+  }
+
+  async #sendResult(result: DispatchedToolResultParams, toolUseId: string): Promise<boolean> {
+    const ctrl = this.#controller;
+    let lastErr: unknown;
+    for (let i = 0; i < SEND_RETRIES; i++) {
+      // An abort throws to unwind the caller rather than returning a
+      // `posted: false` result the iterator would carry on past.
+      ctrl.signal.throwIfAborted();
+      try {
+        await this.client.beta.sessions.events.send(
+          this.sessionId,
+          { events: [result] },
+          this.#requestOptions(),
+        );
+        this.#answered.add(toolUseId);
+        return true;
+      } catch (e) {
+        lastErr = e;
+        // Only short-circuit on a permanent 4xx; 408/409/429 deserve the
+        // remaining retries (aligned with the core client's retry policy).
+        if (isFatal4xx(e)) break;
+        // Back off only *between* attempts — never after the final one, since
+        // there is no further try left to wait for.
+        if (i < SEND_RETRIES - 1) await sleep((i + 1) * 1000, ctrl.signal);
+      }
+    }
+    this.#logger.error('failed to send tool result', {
+      tool_use_id: toolUseId,
+      error: String(lastErr),
+    });
+    return false;
+  }
+
+  /** Wait (bounded) for in-flight tool executions to finish during teardown. */
+  async #drain(): Promise<void> {
+    if (this.#inFlightCount === 0) return;
+    await Promise.race([new Promise<void>((r) => (this.#onIdle = r)), sleep(DRAIN_TIMEOUT_MS)]);
+    this.#onIdle = null;
+    if (this.#inFlightCount > 0) {
+      this.#logger.warn('drain timeout exceeded');
+    }
+  }
+}
+
+/**
+ * Build the result event that answers `ev`: a `user.tool_result` for a builtin
+ * `agent.tool_use`, a `user.custom_tool_result` for a custom
+ * `agent.custom_tool_use`. The two `(use, result)` pairs are distinct API event
+ * types and must be matched exactly — a `user.tool_result` does not answer a
+ * custom tool call.
+ */
+function buildResultEvent(
+  ev: DispatchedToolUseEvent,
+  isError: boolean,
+  content: SessionContentBlock[],
+): DispatchedToolResultParams {
+  if (ev.type === 'agent.custom_tool_use') {
+    return { type: 'user.custom_tool_result', custom_tool_use_id: ev.id, is_error: isError, content };
+  }
+  return { type: 'user.tool_result', tool_use_id: ev.id, is_error: isError, content };
+}
+
+// The Messages-API tool-result block union is wider than the Sessions-API
+// tool_result content union; pass through text/image/document and stringify
+// anything else so a BetaRunnableTool authored for toolRunner still works here.
+function toSessionContent(content: string | Array<BetaToolResultContentBlockParam>): SessionContentBlock[] {
+  if (typeof content === 'string') return [{ type: 'text', text: content || '(no output)' }];
+  const out = content.map((b): SessionContentBlock => {
+    if (b.type === 'text') return { type: 'text', text: b.text || '(no output)' };
+    if (b.type === 'image' || b.type === 'document') return b as SessionContentBlock;
+    if (b.type === 'search_result') {
+      // The Messages `search_result` block param maps field-for-field onto the
+      // Sessions `BetaManagedAgentsSearchResultBlock`; map it explicitly rather
+      // than letting it fall through to the JSON.stringify branch (which would
+      // bury a structured result inside a text block). `citations` is required
+      // on the Sessions side and optional on the Messages side — default the
+      // flag to `false` when the producer left it unset.
+      return {
+        type: 'search_result',
+        source: b.source,
+        title: b.title,
+        content: b.content.map((c) => ({ type: 'text', text: c.text })),
+        citations: { enabled: b.citations?.enabled ?? false },
+      };
+    }
+    return { type: 'text', text: JSON.stringify(b) };
+  });
+  return out.length > 0 ? out : [{ type: 'text', text: '(no output)' }];
+}

package/src/lib/tools/ToolError.ts

@@ -0,0 +1,47 @@
+import { BetaToolResultContentBlockParam } from '../../resources/beta';
+
+/**
+ * An error that can be thrown from a tool's `run` method to return structured
+ * content blocks as the error result, rather than just a string message.
+ *
+ * When the ToolRunner catches this error, it will use the `content` property
+ * as the tool result with `is_error: true`.
+ *
+ * @example
+ * ```ts
+ * const tool = {
+ *   name: 'my_tool',
+ *   run: async (input) => {
+ *     if (somethingWentWrong) {
+ *       throw new ToolError([
+ *         { type: 'text', text: 'Error details here' },
+ *         { type: 'image', source: { type: 'base64', data: '...', media_type: 'image/png' } },
+ *       ]);
+ *     }
+ *     return 'success';
+ *   },
+ * };
+ * ```
+ */
+export class ToolError extends Error {
+  /**
+   * The content to return as the tool result. This will be sent back to the model
+   * with `is_error: true`.
+   */
+  readonly content: string | Array<BetaToolResultContentBlockParam>;
+
+  constructor(content: string | Array<BetaToolResultContentBlockParam>) {
+    const message =
+      typeof content === 'string' ? content : (
+        content
+          .map((block) => {
+            if (block.type === 'text') return block.text;
+            return `[${block.type}]`;
+          })
+          .join(' ')
+      );
+    super(message);
+    this.name = 'ToolError';
+    this.content = content;
+  }
+}