diff --git a/src/mcp/server/lowlevel/server.py b/src/mcp/server/lowlevel/server.py
index 2dd1a8277..b6dc913e6 100644
--- a/src/mcp/server/lowlevel/server.py
+++ b/src/mcp/server/lowlevel/server.py
@@ -537,6 +537,8 @@ async def handler(req: types.CallToolRequest):
                     # output normalization
                     unstructured_content: UnstructuredContent
                     maybe_structured_content: StructuredContent | None
+                    is_error = False
+
                     if isinstance(results, types.CallToolResult):
                         return types.ServerResult(results)
                     elif isinstance(results, types.CreateTaskResult):
@@ -556,12 +558,18 @@ async def handler(req: types.CallToolRequest):
                     else:  # pragma: no cover
                         return self._make_error_result(f"Unexpected return type from tool: {type(results).__name__}")
 
-                    # output validation
+                    # output validation: a tool with an outputSchema must still
+                    # be able to surface a tool-execution failure via unstructured
+                    # content. If structured output is missing for such a tool,
+                    # treat the unstructured payload as a tool-error result
+                    # (isError=true) instead of replacing it with a hard
+                    # "outputSchema defined but no structured output returned"
+                    # error that obscures the original failure message. This
+                    # mirrors the TypeScript SDK fix in
+                    # modelcontextprotocol/typescript-sdk#655.
                     if tool and tool.outputSchema is not None:
                         if maybe_structured_content is None:
-                            return self._make_error_result(
-                                "Output validation error: outputSchema defined but no structured output returned"
-                            )
+                            is_error = True
                         else:
                             try:
                                 jsonschema.validate(instance=maybe_structured_content, schema=tool.outputSchema)
@@ -573,7 +581,7 @@ async def handler(req: types.CallToolRequest):
                         types.CallToolResult(
                             content=list(unstructured_content),
                             structuredContent=maybe_structured_content,
-                            isError=False,
+                            isError=is_error,
                         )
                     )
                 except UrlElicitationRequiredError:
diff --git a/tests/server/test_lowlevel_output_validation.py b/tests/server/test_lowlevel_output_validation.py
index f73544521..30bbd91be 100644
--- a/tests/server/test_lowlevel_output_validation.py
+++ b/tests/server/test_lowlevel_output_validation.py
@@ -213,8 +213,15 @@ async def test_callback(client_session: ClientSession) -> CallToolResult:
 
 
 @pytest.mark.anyio
-async def test_content_only_with_output_schema_error():
-    """Test error when outputSchema is defined but only content is returned."""
+async def test_content_only_with_output_schema_surfaces_error():
+    """When an outputSchema-bound tool returns only unstructured content,
+    the result is treated as a tool-error (isError=True) and the original
+    unstructured payload is preserved so the caller sees the tool's own
+    error message instead of a generic validation message.
+
+    Mirrors the TypeScript SDK fix in modelcontextprotocol/typescript-sdk#655.
+    See #2429 for the original report.
+    """
     tools = [
         Tool(
             name="structured_tool",
@@ -234,7 +241,10 @@ async def test_content_only_with_output_schema_error():
     ]
 
     async def call_tool_handler(name: str, arguments: dict[str, Any]) -> list[TextContent]:
-        # This returns only content, but outputSchema expects structured data
+        # This returns only content, but outputSchema expects structured data.
+        # Real-world callers use this path to surface tool-execution errors
+        # like "Resource not found" or "API rate limit hit"; that text must
+        # not be replaced by a generic validation message.
         return [TextContent(type="text", text="This is not structured")]
 
     async def test_callback(client_session: ClientSession) -> CallToolResult:
@@ -242,13 +252,16 @@ async def test_callback(client_session: ClientSession) -> CallToolResult:
 
     result = await run_tool_test(tools, call_tool_handler, test_callback)
 
-    # Verify error
+    # Result is flagged as an error (isError=True) so callers can detect it,
+    # but the tool's original unstructured payload is preserved verbatim.
     assert result is not None
     assert result.isError
     assert len(result.content) == 1
     assert result.content[0].type == "text"
     assert isinstance(result.content[0], TextContent)
-    assert "Output validation error: outputSchema defined but no structured output returned" in result.content[0].text
+    assert result.content[0].text == "This is not structured"
+    # No structured content was produced; that field stays None.
+    assert result.structuredContent is None
 
 
 @pytest.mark.anyio