diff --git a/docs/contributing/tool-responses.md b/docs/contributing/tool-responses.md
index 2805c164c..020321803 100644
--- a/docs/contributing/tool-responses.md
+++ b/docs/contributing/tool-responses.md
@@ -107,6 +107,10 @@ Translate upstream API shapes into user-facing terms:
   identifiers needed for follow-up.
 - Drop empty, nullish, or unknown placeholder values before rendering details.
 - Cap long repeated lists and say how many additional items were omitted.
+- Truncate long text with plain `slice`. A cut can leave half of an emoji, and
+  strict JSON clients such as Codex reject that lone surrogate, so the server
+  replaces it with U+FFFD in every tool response. Formatters do not need
+  surrogate-aware slicing.
 - Prefer shared helpers for dates, actors, IDs, and unknown values. If a helper
   emits noisy placeholders for a domain-specific field, filter before calling it.
 
diff --git a/packages/mcp-core/src/server.test.ts b/packages/mcp-core/src/server.test.ts
index 69667785e..c158986f8 100644
--- a/packages/mcp-core/src/server.test.ts
+++ b/packages/mcp-core/src/server.test.ts
@@ -3,6 +3,7 @@ import { InMemoryTransport } from "@modelcontextprotocol/sdk/inMemory.js";
 import { McpServer as ModernMcpServer } from "@modelcontextprotocol/server";
 import { type Span, setUser, startSpan } from "@sentry/core";
 import {
+  eventFixture,
   issueFixture,
   mswServer,
   projectFixture,
@@ -316,6 +317,98 @@ describe("buildServer", () => {
     },
   );
 
+  describe("lone surrogates in tool output", () => {
+    // Cutting 119 characters plus an emoji at 120 UTF-16 units keeps only the
+    // emoji's high surrogate. Strict JSON parsers such as serde_json in Codex
+    // reject that lone half and close the transport.
+    const lock = "\u{1F512}";
+    const cutText = `${"x".repeat(119)}${lock}`.slice(0, 120);
+    const replacedText = `${"x".repeat(119)}�`;
+
+    it("replaces a breadcrumb message cut inside an emoji", async () => {
+      mswServer.use(
+        http.get(
+          "https://sentry.io/api/0/organizations/sentry-mcp-evals/issues/CLOUDFLARE-MCP-41/events/latest/",
+          () =>
+            HttpResponse.json({
+              ...eventFixture,
+              entries: [
+                {
+                  type: "breadcrumbs",
+                  data: {
+                    values: [
+                      {
+                        timestamp: "2025-04-08T21:14:52.000Z",
+                        category: "console",
+                        level: "info",
+                        message: `${"x".repeat(119)}${lock} required`,
+                      },
+                    ],
+                  },
+                },
+              ],
+            }),
+          { once: true },
+        ),
+      );
+
+      const result = await callRegisteredTool(
+        buildServer({ context: baseContext }),
+        "execute_sentry_tool",
+        {
+          name: "get_issue_breadcrumbs",
+          arguments: {
+            organizationSlug: "sentry-mcp-evals",
+            issueId: "CLOUDFLARE-MCP-41",
+          },
+        },
+      );
+
+      const text = getTextContent(result);
+      expect(text).toContain(`[console] ${replacedText}...`);
+      expect(text.isWellFormed()).toBe(true);
+    });
+
+    it("replaces them in structured and error output", async () => {
+      const createServer = () =>
+        buildServer({
+          context: baseContext,
+          tools: {
+            structured_tool: createMockTool("structured_tool", {
+              outputSchema: z.object({ preview: z.string() }),
+              handler: async () => structuredResult({ preview: cutText }),
+            }),
+            failing_tool: createMockTool("failing_tool", {
+              handler: async () => {
+                throw new UserInputError(cutText);
+              },
+            }),
+          },
+        });
+
+      const structured = await callRegisteredTool(
+        createServer(),
+        "structured_tool",
+        {},
+      );
+      expect(getStructuredContent(structured)).toEqual({
+        preview: replacedText,
+      });
+      expect(getTextContent(structured)).toBe(
+        getGeneratedTextFromStructuredContent(structured),
+      );
+
+      const failed = await callRegisteredTool(
+        createServer(),
+        "failing_tool",
+        {},
+      );
+      expect(failed).toMatchObject({ isError: true });
+      expect(getTextContent(failed)).toContain(replacedText);
+      expect(getTextContent(failed).isWellFormed()).toBe(true);
+    });
+  });
+
   describe("telemetry context", () => {
     it("generates compatibility text for structured-only tool output", async () => {
       const server = buildServer({
diff --git a/packages/mcp-core/src/server.ts b/packages/mcp-core/src/server.ts
index 2c99ba6e3..52aa7ea37 100644
--- a/packages/mcp-core/src/server.ts
+++ b/packages/mcp-core/src/server.ts
@@ -105,6 +105,36 @@ function structuredOutputToCallToolResult(
   };
 }
 
+/**
+ * Replaces lone UTF-16 surrogates in tool output with U+FFFD.
+ *
+ * Formatters truncate upstream text by UTF-16 index, so a cut can keep only
+ * half of an emoji. `JSON.stringify` writes that half as `\ud83d`, and strict
+ * JSON parsers such as serde_json in Codex reject the message and close the
+ * transport. Normalizing handler output here covers every tool, including
+ * structuredContent and the compatibility text generated from it.
+ */
+function toWellFormedOutput<T>(value: T): T {
+  if (typeof value === "string") {
+    return value.toWellFormed() as T;
+  }
+  if (Array.isArray(value)) {
+    return value.map(toWellFormedOutput) as T;
+  }
+  if (value !== null && typeof value === "object") {
+    const prototype = Object.getPrototypeOf(value);
+    if (prototype === Object.prototype || prototype === null) {
+      return Object.fromEntries(
+        Object.entries(value).map(([key, item]) => [
+          key.toWellFormed(),
+          toWellFormedOutput(item),
+        ]),
+      ) as T;
+    }
+  }
+  return value;
+}
+
 /**
  * Creates and configures a complete MCP server with Sentry instrumentation.
  *
@@ -349,11 +379,13 @@ function configureServer({
           }
         }
 
-        const output = await executeToolHandler({
-          tool,
-          params: rawParams,
-          context: contextWithToolAvailability,
-        });
+        const output = toWellFormedOutput(
+          await executeToolHandler({
+            tool,
+            params: rawParams,
+            context: contextWithToolAvailability,
+          }),
+        );
 
         if (activeSpan) {
           activeSpan.setStatus({
@@ -435,9 +467,11 @@ function configureServer({
           content: [
             {
               type: "text" as const,
-              text: await formatErrorForUser(error, {
-                transport: context.transport,
-              }),
+              text: (
+                await formatErrorForUser(error, {
+                  transport: context.transport,
+                })
+              ).toWellFormed(),
             },
           ],
           isError: true,
diff --git a/packages/mcp-server-tsconfig/tsconfig.base.json b/packages/mcp-server-tsconfig/tsconfig.base.json
index 943b1ffe7..96f158583 100644
--- a/packages/mcp-server-tsconfig/tsconfig.base.json
+++ b/packages/mcp-server-tsconfig/tsconfig.base.json
@@ -3,7 +3,7 @@
   "display": "Default",
   "compilerOptions": {
     "target": "ES2022",
-    "lib": ["ES2023"],
+    "lib": ["ES2023", "ES2024.String"],
     "module": "ESNext",
     "preserveWatchOutput": true,