diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
index b4fd678a4594..11110bf389d5 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
@@ -2676,6 +2676,66 @@ describe("ClaudeAdapterV2 background wake turns", () => {
     ),
   );
 
+  for (const terminalReason of [
+    "api_error",
+    "malformed_tool_use_exhausted",
+    "budget_exhausted",
+    "structured_output_retry_exhausted",
+    "tool_deferred_unavailable",
+    "turn_setup_failed",
+    "blocking_limit",
+    "rapid_refill_breaker",
+    "prompt_too_long",
+    "image_error",
+    "model_error",
+    "overloaded_status",
+  ] as const) {
+    it.effect(`fails a success-shaped Claude result with ${terminalReason}`, () =>
+      Effect.scoped(
+        Effect.gen(function* () {
+          const harness = yield* makeWakeHarness;
+          const now = yield* DateTime.now;
+          yield* harness.runtime.startTurn(
+            makeClaudeTestTurnInput({
+              threadId: harness.threadId,
+              providerThread: harness.providerThread,
+              now,
+              attemptId: RunAttemptId.make("attempt-structured-terminal-failure"),
+              text: "Complete the task.",
+              attachments: [],
+            }),
+          );
+          yield* Queue.offer(
+            harness.sdkMessages,
+            makeResultFrame({
+              uuid: "00000000-0000-4000-8000-000000000205",
+              result: "Provider failure details.",
+              isError: false,
+              ...(terminalReason === "overloaded_status"
+                ? { apiErrorStatus: 529 }
+                : { terminalReason }),
+            }),
+          );
+          const terminal = yield* Queue.take(harness.terminalReceipts);
+          assert.equal(terminal.status, "failed");
+          if (terminal.status !== "failed") return;
+          assert.isNotEmpty(terminal.failure.message);
+          assert.isFalse(
+            harness.events.some(
+              (event) =>
+                event.type === "message.updated" &&
+                event.message.text === "Provider failure details.",
+            ),
+          );
+          assert.equal(
+            terminal.failure.code,
+            terminalReason === "overloaded_status" ? "api_error_529" : terminalReason,
+          );
+        }).pipe(Effect.provide(Layer.merge(idAllocatorLayer, NodeServices.layer))),
+      ),
+    );
+  }
+
   const providerThreadRosterEvents = (events: ReadonlyArray<ProviderAdapterV2Event>) =>
     events.filter(
       (event): event is Extract<ProviderAdapterV2Event, { type: "provider_thread.updated" }> =>
diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
index a5d40f87e378..c1d4f1cabac9 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
@@ -2127,7 +2127,10 @@ function providerFailureFromResult(
   const apiErrorStatus = message.api_error_status ?? null;
   return makeProviderFailure({
     message: listedError ?? structuredError ?? failureHint ?? message.result,
-    code: apiErrorStatus === null ? "sdk_result_error" : `api_error_${apiErrorStatus}`,
+    code:
+      apiErrorStatus === null
+        ? (message.terminal_reason ?? "sdk_result_error")
+        : `api_error_${apiErrorStatus}`,
     class: "provider_error",
     retryable: apiErrorStatus === 429 || apiErrorStatus === 529 ? true : null,
   });
@@ -4994,10 +4997,12 @@ export function makeClaudeAdapterV2(
             });
           }
 
-          // An is_error result's text is the error message; it belongs on the
-          // terminal-failure item, not on a synthetic assistant message.
+          // Failed result text belongs on the terminal-failure item, including
+          // structured failures whose SDK result still has is_error=false.
           const resultText =
-            message.type === "result" && message.subtype === "success" && message.is_error
+            message.type === "result" &&
+            ((message.subtype === "success" && message.is_error) ||
+              terminalStatusFromResult(message) === "failed")
               ? null
               : resultTextFromSdkMessage(message);
           if (