diff --git a/src/adapters/openai-responses.ts b/src/adapters/openai-responses.ts
index d60bd6ce1f..18070ddc71 100644
--- a/src/adapters/openai-responses.ts
+++ b/src/adapters/openai-responses.ts
@@ -1014,15 +1014,32 @@ function annotateEmptyResponsesToolOutputs(body: unknown, enabled: boolean): unk
  * call lives behind `previous_response_id`, so ordinary orphan repair cannot run universally.
  * A missing or empty `call_id`, however, cannot identify stored state on any destination.
  */
-function repairUnidentifiedToolOutputItems(body: unknown): unknown {
+export function repairUnidentifiedToolOutputItems(
+  body: unknown,
+  options?: { preserveExternalTaskEnvelopes?: boolean },
+): unknown {
   if (!isPlainObject(body) || !Array.isArray(body.input)) return body;
   let changed = false;
   const input = body.input.map(item => {
-    if (!isPlainObject(item)
-      || (item.type !== "function_call_output" && item.type !== "custom_tool_call_output")
-      || (typeof item.call_id === "string" && item.call_id.length > 0)) {
+    if (!isPlainObject(item)) return item;
+    const isToolOutput = item.type === "function_call_output" || item.type === "custom_tool_call_output" || item.type === "tool_search_output";
+    if (!isToolOutput) return item;
+    const hasValidCallId = typeof item.call_id === "string" && item.call_id.length > 0;
+    if (hasValidCallId) return item;
+    // Translating parse-time repair must leave Codex external-task envelopes alone so
+    // the parser can admit complete ones and fail closed on invalid ones. Passthrough
+    // still converts the raw item because it never reads parsed messages.
+    if (options?.preserveExternalTaskEnvelopes && "id" in item && "name" in item && "namespace" in item) {
       return item;
     }
+    if (item.type === "tool_search_output") {
+      changed = true;
+      return {
+        type: "message",
+        role: "user",
+        content: orphanedToolOutputContent(item.error || item.status || "tool_search"),
+      };
+    }
     if (!isRepairableToolOutput(item.output)) return item;
     changed = true;
     return {
diff --git a/src/server/responses/core.ts b/src/server/responses/core.ts
index b961e7cef9..b4addc50eb 100644
--- a/src/server/responses/core.ts
+++ b/src/server/responses/core.ts
@@ -37,7 +37,7 @@ import {
 } from "../../responses/reasoning-replay-cache";
 import { awaitThoughtSignatureDurability, thoughtSignatureReplaySalt } from "../../responses/thought-signature-replay";
 import { buildCompactV1Output, COMPACT_PROMPT, decodeCompactionSummary, extractCompactUserMessages } from "../../responses/compaction";
-import { FORWARD_HEADERS, sanitizeReasoningInputContent } from "../../adapters/openai-responses";
+import { FORWARD_HEADERS, sanitizeReasoningInputContent, repairUnidentifiedToolOutputItems } from "../../adapters/openai-responses";
 import { XaiToolSchemaCompatibilityError } from "../../adapters/xai-tool-schema";
 import {
   copyPreviousResponseReplayProvenance,
@@ -3222,6 +3222,7 @@ async function handleResponsesInner(
   let parsed: OcxParsedRequest;
   let toolBridgeMaps: ReturnType<typeof buildToolBridgeMaps>;
   try {
+    body = repairUnidentifiedToolOutputItems(body, { preserveExternalTaskEnvelopes: true }) as typeof body;
     parsed = parseRequest(body);
     parsed._promptCacheKeyIsSharedCohort = options.promptCacheKeyIsSharedCohort;
     // Captured before any parser mutates it, so both grammars see the client's id.
@@ -3538,6 +3539,7 @@ async function handleResponsesInner(
       );
       if (!unreadableEncryptedAgentTask) {
         try {
+          body = repairUnidentifiedToolOutputItems(body, { preserveExternalTaskEnvelopes: true }) as typeof body;
           const reparsed = parseRequest(body);
           const kept: Array<keyof OcxParsedRequest> = [
             "_previousResponseInputExpanded",
@@ -6096,7 +6098,9 @@ async function handleResponsesInner(
           || (message as { toolCallId: string }).toolCallId.length === 0),
     );
     if (unpaired) {
-      // Never interpolate the tool output: this message reaches the client and the logs.
+      // Ordinary missing/empty call_id items are rewritten before parseRequest.
+      // Anything still unpaired here is envelope-shaped or otherwise unrepairable:
+      // fail closed without interpolating the tool output into a client-visible message.
       return formatErrorResponse(
         400,
         "invalid_request_error",
diff --git a/tests/responses/responses-compaction-routing.test.ts b/tests/responses/responses-compaction-routing.test.ts
index fafbbd6806..7c46d642e4 100644
--- a/tests/responses/responses-compaction-routing.test.ts
+++ b/tests/responses/responses-compaction-routing.test.ts
@@ -2576,11 +2576,19 @@ describe("unpaired tool result boundary (#3259)", () => {
     },
   } as unknown as OcxConfig);
 
-  test("a translating adapter rejects a call_id-less tool result with 400 and sends nothing upstream", async () => {
-    let fetches = 0;
-    globalThis.fetch = (async () => {
-      fetches += 1;
-      throw new Error("the guard must reject before any upstream request");
+  test("a translating adapter converts a call_id-less tool result into user context", async () => {
+    const bodies: string[] = [];
+    globalThis.fetch = (async (_url: unknown, init?: RequestInit) => {
+      bodies.push(String(init?.body ?? ""));
+      return jsonResponse({
+        id: "msg_1",
+        type: "message",
+        role: "assistant",
+        model: "claude",
+        content: [{ type: "text", text: "ok" }],
+        stop_reason: "end_turn",
+        usage: { input_tokens: 1, output_tokens: 1 },
+      });
     }) as typeof fetch;
 
     const res = await handleResponses(
@@ -2589,19 +2597,25 @@ describe("unpaired tool result boundary (#3259)", () => {
       { model: "", provider: "" },
     );
 
-    expect(res.status).toBe(400);
-    const json = await res.json() as { error?: { message?: string; type?: string; code?: string } };
-    expect(json.error?.message).toBe("tool result requires a non-empty string call_id");
-    expect(json.error?.type).toBe("invalid_request_error");
-    expect(json.error?.code).toBe("invalid_request_error");
-    // The tool output itself must never be interpolated into a client-visible message.
-    expect(JSON.stringify(json)).not.toContain("bootstrap result");
-    expect(fetches).toBe(0);
+    expect(res.status).toBe(200);
+    expect(bodies).toHaveLength(1);
+    expect(bodies[0]).toContain("bootstrap result");
+    expect(bodies[0]).not.toContain("undefined");
   });
 
-  test("an empty-string call_id is rejected identically (it can never pair)", async () => {
-    globalThis.fetch = (async () => {
-      throw new Error("the guard must reject before any upstream request");
+  test("an empty-string call_id is converted identically (it can never pair)", async () => {
+    const bodies: string[] = [];
+    globalThis.fetch = (async (_url: unknown, init?: RequestInit) => {
+      bodies.push(String(init?.body ?? ""));
+      return jsonResponse({
+        id: "msg_1",
+        type: "message",
+        role: "assistant",
+        model: "claude",
+        content: [{ type: "text", text: "ok" }],
+        stop_reason: "end_turn",
+        usage: { input_tokens: 1, output_tokens: 1 },
+      });
     }) as typeof fetch;
 
     const res = await handleResponses(
@@ -2609,7 +2623,34 @@ describe("unpaired tool result boundary (#3259)", () => {
       anthropicConfig(),
       { model: "", provider: "" },
     );
-    expect(res.status).toBe(400);
+    expect(res.status).toBe(200);
+    expect(bodies).toHaveLength(1);
+  });
+
+  test("a call_id-less tool_search_output is converted into user context", async () => {
+    const bodies: string[] = [];
+    globalThis.fetch = (async (_url: unknown, init?: RequestInit) => {
+      bodies.push(String(init?.body ?? ""));
+      return jsonResponse({
+        id: "msg_1",
+        type: "message",
+        role: "assistant",
+        model: "claude",
+        content: [{ type: "text", text: "ok" }],
+        stop_reason: "end_turn",
+        usage: { input_tokens: 1, output_tokens: 1 },
+      });
+    }) as typeof fetch;
+
+    const res = await handleResponses(
+      compactionRequest(unpairedBody({ type: "tool_search_output", status: "failed" })),
+      anthropicConfig(),
+      { model: "", provider: "" },
+    );
+    expect(res.status).toBe(200);
+    expect(bodies).toHaveLength(1);
+    expect(bodies[0]).toContain("failed");
+    expect(bodies[0]).not.toContain("undefined");
   });
 
   test("a paired tool result on the same translating route still reaches the upstream", async () => {