diff --git a/src/mcp/server/mcpserver/exceptions.py b/src/mcp/server/mcpserver/exceptions.py
index 5e831b1238..25b5ae22f9 100644
--- a/src/mcp/server/mcpserver/exceptions.py
+++ b/src/mcp/server/mcpserver/exceptions.py
@@ -55,8 +55,18 @@ class ToolError(MCPServerError):
     The SDK raises it too, for an unknown tool name and for arguments that fail
     the input schema, and `UnexpectedToolError` subclasses it, so `except ToolError`
     around `MCPServer.call_tool()` catches every tool failure, crash or not.
+
+    Args:
+        message: The error message for the model to read.
+        content: Optional tool result content to include in the error response.
+            When provided, these content blocks are returned with `is_error=True`
+            instead of a single text block derived from `message`.
     """
 
+    def __init__(self, message: str = "", *args: object, content: object = None) -> None:
+        super().__init__(message, *args)
+        self.content = content
+
 
 class UnexpectedToolError(ToolError):
     """A tool call failed with something other than `ToolError`, `ResourceError`, or `MCPError`.
diff --git a/src/mcp/server/mcpserver/server.py b/src/mcp/server/mcpserver/server.py
index 7efa29108d..8bee6c78cc 100644
--- a/src/mcp/server/mcpserver/server.py
+++ b/src/mcp/server/mcpserver/server.py
@@ -453,6 +453,17 @@ async def _handle_call_tool(
                     logger.info("Tool %r failed: %r", params.name, str(exc))
             else:
                 logger.exception("Tool %r raised an unexpected exception", params.name)
+            if isinstance(exc, ToolError) and not isinstance(exc, UnexpectedToolError) and getattr(exc, "content", None) is not None:
+                from mcp.server.mcpserver.utilities.func_metadata import _convert_to_content
+
+                raw = exc.content
+                if isinstance(raw, (list, tuple)):
+                    blocks: list[Any] = []
+                    for item in raw:
+                        blocks.extend(_convert_to_content(item))
+                else:
+                    blocks = _convert_to_content(raw)
+                return CallToolResult(content=blocks, is_error=True)
             return CallToolResult(content=[TextContent(type="text", text=str(exc))], is_error=True)
 
     async def _handle_list_resources(
diff --git a/src/mcp/server/mcpserver/tools/base.py b/src/mcp/server/mcpserver/tools/base.py
index 10a2d6c489..3ea8860026 100644
--- a/src/mcp/server/mcpserver/tools/base.py
+++ b/src/mcp/server/mcpserver/tools/base.py
@@ -209,7 +209,10 @@ async def run(
             raise UnexpectedToolError(f"Error executing tool {self.name}: {exc}") from exc
         except (ToolError, ResourceError) as exc:
             # Raised deliberately by the tool, a resolver, or a resource it read.
-            raise ToolError(f"Error executing tool {self.name}: {exc}") from exc
+            wrapped = ToolError(f"Error executing tool {self.name}: {exc}")
+            if isinstance(exc, ToolError) and getattr(exc, "content", None) is not None:
+                wrapped.content = exc.content
+            raise wrapped from exc
         except Exception as exc:
             # A crash: the exception's own text stays on the server.
             raise UnexpectedToolError(f"Error executing tool {self.name}") from exc
diff --git a/tests/server/mcpserver/test_server.py b/tests/server/mcpserver/test_server.py
index a266714298..42ee6f09b0 100644
--- a/tests/server/mcpserver/test_server.py
+++ b/tests/server/mcpserver/test_server.py
@@ -2562,6 +2562,44 @@ def spend() -> str:
     )
 
 
+
+async def test_tool_error_with_content_returns_content_in_error_result():
+    """ToolError with content returns that content in the is_error result."""
+    mcp = MCPServer()
+
+    @mcp.tool()
+    def analyze() -> str:
+        raise ToolError(
+            "analysis failed",
+            content=[TextContent(type="text", text="partial output"), ImageContent(type="image", data="YWJj", mime_type="image/png")],
+        )
+
+    async with Client(mcp) as client:
+        result = await client.call_tool("analyze", {})
+
+    assert result.is_error is True
+    assert len(result.content) == 2
+    assert result.content[0] == TextContent(type="text", text="partial output")
+    assert result.content[1] == ImageContent(type="image", data="YWJj", mime_type="image/png")
+
+
+async def test_tool_error_with_image_helper_content_returns_image_in_error_result():
+    """ToolError with Image helper content converts to ImageContent in is_error result."""
+    mcp = MCPServer()
+
+    @mcp.tool()
+    def screenshot() -> str:
+        raise ToolError("capture failed", content=[Image(data=b"abc", format="png")])
+
+    async with Client(mcp) as client:
+        result = await client.call_tool("screenshot", {})
+
+    assert result.is_error is True
+    assert len(result.content) == 1
+    assert result.content[0].type == "image"
+    assert result.content[0].mime_type == "image/png"
+
+
 async def test_tool_argument_validation_failure_is_logged_at_info_without_traceback(
     caplog: pytest.LogCaptureFixture,
 ):