fix(agent): classify upstream prompt failures without replay

packages/agent/src/adapters/claude/conversion/sdk-to-acp.ts

@@ -608,6 +608,32 @@ export type ResultMessageHandlerResult = {
   };
 };
 
+export type AgentErrorClassification =
+  | "upstream_stream_terminated"
+  | "upstream_connection_error"
+  | "agent_error";
+
+/**
+ * Classify an error string surfaced by the Claude CLI via `is_error: true`
+ * result messages. Transient upstream-stream terminations (e.g. the fetch body
+ * from the LLM gateway is torn down mid-stream) are retriable; most other
+ * errors are not.
+ */
+export function classifyAgentError(
+  result: string | undefined,
+): AgentErrorClassification {
+  if (!result) return "agent_error";
+  const text = result.trim();
+  // Anthropic SDK surfaces an undici fetch abort as "API Error: terminated".
+  if (/API Error:\s*terminated\b/i.test(text)) {
+    return "upstream_stream_terminated";
+  }
+  if (/API Error:\s*Connection error\b/i.test(text)) {
+    return "upstream_connection_error";
+  }
+  return "agent_error";
+}
+
 export function handleResultMessage(
   message: SDKResultMessage,
 ): ResultMessageHandlerResult {
@@ -626,9 +652,13 @@ export function handleResultMessage(
         return { shouldStop: true, stopReason: "max_tokens", usage };
       }
       if (message.is_error) {
+        const classification = classifyAgentError(message.result);
         return {
           shouldStop: true,
-          error: RequestError.internalError(undefined, message.result),
+          error: RequestError.internalError(
+            { classification, result: message.result },
+            message.result,
+          ),
           usage,
         };
       }

packages/agent/src/server/agent-server.ts

@@ -17,6 +17,10 @@ import {
   createAcpConnection,
   type InProcessAcpConnection,
 } from "../adapters/acp-connection";
+import {
+  type AgentErrorClassification,
+  classifyAgentError,
+} from "../adapters/claude/conversion/sdk-to-acp";
 import { selectRecentTurns } from "../adapters/claude/session/jsonl-hydration";
 import type { PermissionMode } from "../execution-mode";
 import { DEFAULT_CODEX_MODEL } from "../gateway-models";
@@ -949,6 +953,50 @@ export class AgentServer {
     await this.sendInitialTaskMessage(payload, preTaskRun);
   }
 
+  private extractErrorClassification(error: unknown): {
+    classification: AgentErrorClassification;
+    message: string;
+  } {
+    const message =
+      error instanceof Error ? error.message : String(error ?? "");
+
+    // Prefer the structured `data` carried on RequestError if present.
+    const data = (error as { data?: unknown } | undefined)?.data;
+    if (
+      data &&
+      typeof data === "object" &&
+      "classification" in data &&
+      typeof (data as { classification: unknown }).classification === "string"
+    ) {
+      return {
+        classification: (data as { classification: AgentErrorClassification })
+          .classification,
+        message,
+      };
+    }
+
+    return { classification: classifyAgentError(message), message };
+  }
+
+  private classifyAndSignalFailure(
+    payload: JwtPayload,
+    phase: "initial" | "resume",
+    error: unknown,
+  ): Promise<void> {
+    const { classification, message } = this.extractErrorClassification(error);
+    const errorMessage =
+      classification === "upstream_stream_terminated"
+        ? "Upstream LLM stream terminated"
+        : classification === "upstream_connection_error"
+          ? "Upstream LLM connection error"
+          : message || "Agent error";
+    this.logger.error(`send_${phase}_task_message_failed`, {
+      classification,
+      message,
+    });
+    return this.signalTaskComplete(payload, "error", errorMessage);
+  }
+
   private async sendInitialTaskMessage(
     payload: JwtPayload,
     prefetchedRun?: TaskRun | null,
@@ -1061,7 +1109,7 @@ export class AgentServer {
       if (this.session) {
         await this.session.logWriter.flushAll();
       }
-      await this.signalTaskComplete(payload, "error");
+      await this.classifyAndSignalFailure(payload, "initial", error);
     }
   }
 
@@ -1150,7 +1198,7 @@ export class AgentServer {
       if (this.session) {
         await this.session.logWriter.flushAll();
       }
-      await this.signalTaskComplete(payload, "error");
+      await this.classifyAndSignalFailure(payload, "resume", error);
     }
   }
 
@@ -1461,6 +1509,7 @@ ${attributionInstructions}
   private async signalTaskComplete(
     payload: JwtPayload,
     stopReason: string,
+    errorMessage?: string,
   ): Promise<void> {
     if (this.session?.payload.run_id === payload.run_id) {
       try {
@@ -1488,7 +1537,7 @@ ${attributionInstructions}
     try {
       await this.posthogAPI.updateTaskRun(payload.task_id, payload.run_id, {
         status,
-        error_message: stopReason === "error" ? "Agent error" : undefined,
+        error_message: errorMessage ?? "Agent error",
       });
       this.logger.info("Task completion signaled", { status, stopReason });
     } catch (error) {

packages/agent/src/server/question-relay.test.ts

@@ -1,5 +1,6 @@
 import { type SetupServerApi, setupServer } from "msw/node";
 import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
+import { classifyAgentError } from "../adapters/claude/conversion/sdk-to-acp";
 import type { PostHogAPIClient } from "../posthog-api";
 import { createTestRepo, type TestRepo } from "../test/fixtures/api";
 import { createPostHogHandlers } from "../test/mocks/msw-handlers";
@@ -49,7 +50,42 @@ const QUESTION_META = {
   ],
 };
 
+function createTransientPromptError(): Error & {
+  data: { classification: string; result: string };
+} {
+  const error = new Error("API Error: terminated") as Error & {
+    data: { classification: string; result: string };
+  };
+  error.data = {
+    classification: "upstream_stream_terminated",
+    result: "API Error: terminated",
+  };
+  return error;
+}
+
+function createTransientConnectionError(): Error & {
+  data: { classification: string; result: string };
+} {
+  const error = new Error("fetch failed") as Error & {
+    data: { classification: string; result: string };
+  };
+  error.data = {
+    classification: "upstream_connection_error",
+    result: "fetch failed",
+  };
+  return error;
+}
+
 describe("Question relay", () => {
+  it.each([
+    ["API Error: terminated", "upstream_stream_terminated"],
+    ["API Error: Connection error", "upstream_connection_error"],
+    ["something else", "agent_error"],
+    [undefined, "agent_error"],
+  ])("classifies %p as %s", (message, expected) => {
+    expect(classifyAgentError(message)).toBe(expected);
+  });
+
   let repo: TestRepo;
   let server: TestableAgentServer;
   let mswServer: SetupServerApi;
@@ -514,5 +550,93 @@ describe("Question relay", () => {
         prompt: [{ type: "text", text: "original task description" }],
       });
     });
+
+    it("does not replay a transient upstream termination before any session activity", async () => {
+      vi.spyOn(server.posthogAPI, "getTask").mockResolvedValue({
+        id: "test-task-id",
+        title: "t",
+        description: "original task description",
+      } as unknown as Task);
+      vi.spyOn(server.posthogAPI, "getTaskRun").mockResolvedValue({
+        id: "test-run-id",
+        task: "test-task-id",
+        state: {},
+      } as unknown as TaskRun);
+
+      const promptSpy = vi
+        .fn()
+        .mockRejectedValueOnce(createTransientPromptError());
+      const updateTaskRunSpy = vi
+        .spyOn(server.posthogAPI, "updateTaskRun")
+        .mockResolvedValue({} as TaskRun);
+      server.session = {
+        payload: TEST_PAYLOAD,
+        acpSessionId: "acp-session",
+        clientConnection: { prompt: promptSpy },
+        logWriter: {
+          flushAll: vi.fn().mockResolvedValue(undefined),
+          getFullAgentResponse: vi.fn().mockReturnValue(null),
+          resetTurnMessages: vi.fn(),
+          flush: vi.fn().mockResolvedValue(undefined),
+          isRegistered: vi.fn().mockReturnValue(true),
+        },
+      };
+
+      await server.sendInitialTaskMessage(TEST_PAYLOAD);
+
+      expect(promptSpy).toHaveBeenCalledTimes(1);
+      expect(updateTaskRunSpy).toHaveBeenCalledWith(
+        "test-task-id",
+        "test-run-id",
+        {
+          status: "failed",
+          error_message: "Upstream LLM stream terminated",
+        },
+      );
+    });
+
+    it("surfaces upstream connection errors with the connection-specific message", async () => {
+      vi.spyOn(server.posthogAPI, "getTask").mockResolvedValue({
+        id: "test-task-id",
+        title: "t",
+        description: "original task description",
+      } as unknown as Task);
+      vi.spyOn(server.posthogAPI, "getTaskRun").mockResolvedValue({
+        id: "test-run-id",
+        task: "test-task-id",
+        state: {},
+      } as unknown as TaskRun);
+
+      const promptSpy = vi.fn().mockImplementationOnce(async () => {
+        throw createTransientConnectionError();
+      });
+      const updateTaskRunSpy = vi
+        .spyOn(server.posthogAPI, "updateTaskRun")
+        .mockResolvedValue({} as TaskRun);
+      server.session = {
+        payload: TEST_PAYLOAD,
+        acpSessionId: "acp-session",
+        clientConnection: { prompt: promptSpy },
+        logWriter: {
+          flushAll: vi.fn().mockResolvedValue(undefined),
+          getFullAgentResponse: vi.fn().mockReturnValue(null),
+          resetTurnMessages: vi.fn(),
+          flush: vi.fn().mockResolvedValue(undefined),
+          isRegistered: vi.fn().mockReturnValue(true),
+        },
+      };
+
+      await server.sendInitialTaskMessage(TEST_PAYLOAD);
+
+      expect(promptSpy).toHaveBeenCalledTimes(1);
+      expect(updateTaskRunSpy).toHaveBeenCalledWith(
+        "test-task-id",
+        "test-run-id",
+        {
+          status: "failed",
+          error_message: "Upstream LLM connection error",
+        },
+      );
+    });
   });
 });