diff --git a/src/mcp/server/fastmcp/utilities/types.py b/src/mcp/server/fastmcp/utilities/types.py
index d6928ca3f..2a8d6c157 100644
--- a/src/mcp/server/fastmcp/utilities/types.py
+++ b/src/mcp/server/fastmcp/utilities/types.py
@@ -2,6 +2,10 @@
 
 import base64
 from pathlib import Path
+from typing import Any
+
+from pydantic import GetCoreSchemaHandler
+from pydantic_core import CoreSchema, core_schema
 
 from mcp.types import AudioContent, ImageContent
 
@@ -53,6 +57,23 @@ def to_image_content(self) -> ImageContent:
 
         return ImageContent(type="image", data=data, mimeType=self._mime_type)
 
+    @classmethod
+    def __get_pydantic_core_schema__(
+        cls,
+        source_type: Any,
+        handler: GetCoreSchemaHandler,
+    ) -> CoreSchema:
+        # Serialize Image as ImageContent so it round-trips through any
+        # Pydantic-driven JSON encoder (e.g. CallToolResult.model_dump_json).
+        # Validation accepts an existing Image instance unchanged; new instances
+        # are constructed through the regular __init__, not via this schema.
+        return core_schema.no_info_plain_validator_function(
+            function=lambda value: value,
+            serialization=core_schema.plain_serializer_function_ser_schema(
+                lambda instance: instance.to_image_content().model_dump(mode="json", by_alias=True),
+            ),
+        )
+
 
 class Audio:
     """Helper class for returning audio from tools."""
@@ -99,3 +120,19 @@ def to_audio_content(self) -> AudioContent:
             raise ValueError("No audio data available")
 
         return AudioContent(type="audio", data=data, mimeType=self._mime_type)
+
+    @classmethod
+    def __get_pydantic_core_schema__(
+        cls,
+        source_type: Any,
+        handler: GetCoreSchemaHandler,
+    ) -> CoreSchema:
+        # Serialize Audio as AudioContent so it round-trips through any
+        # Pydantic-driven JSON encoder. See ``Image.__get_pydantic_core_schema__``
+        # for the rationale.
+        return core_schema.no_info_plain_validator_function(
+            function=lambda value: value,
+            serialization=core_schema.plain_serializer_function_ser_schema(
+                lambda instance: instance.to_audio_content().model_dump(mode="json", by_alias=True),
+            ),
+        )
diff --git a/tests/issues/test_2376_image_stateless_http.py b/tests/issues/test_2376_image_stateless_http.py
new file mode 100644
index 000000000..2fd15fd16
--- /dev/null
+++ b/tests/issues/test_2376_image_stateless_http.py
@@ -0,0 +1,109 @@
+"""Regression test for issue #2376.
+
+Image (and Audio) helpers returned from FastMCP tools must serialize to the
+``ImageContent``/``AudioContent`` wire shape, including when stateless HTTP
+mode is used by remote MCP clients.
+
+The original report described
+``Unable to serialize unknown type: mcp.server.fastmcp.utilities.types.Image``
+from ``pydantic_core`` when the helper bypassed ``_convert_to_content`` and
+was handed straight to Pydantic's JSON encoder. The fix gives ``Image`` and
+``Audio`` a Pydantic core schema so any Pydantic-driven serializer produces
+the right shape.
+"""
+
+import base64
+
+import httpx
+import pytest
+from pydantic import BaseModel
+
+from mcp.server.fastmcp import FastMCP
+from mcp.server.fastmcp.utilities.types import Audio, Image
+
+
+class _Holder(BaseModel):
+    """Pydantic model used to round-trip helper instances through serialization."""
+
+    model_config = {"arbitrary_types_allowed": True}
+
+    image: Image | None = None
+    audio: Audio | None = None
+
+
+def test_image_serializes_as_image_content_via_pydantic() -> None:
+    """Image must serialize as ImageContent when handed to a Pydantic encoder."""
+    holder = _Holder(image=Image(data=b"hello", format="png"))
+    dumped = holder.model_dump(mode="json", by_alias=True)["image"]
+    assert dumped["type"] == "image"
+    assert dumped["mimeType"] == "image/png"
+    assert base64.b64decode(dumped["data"]) == b"hello"
+
+
+def test_audio_serializes_as_audio_content_via_pydantic() -> None:
+    """Audio must serialize as AudioContent when handed to a Pydantic encoder."""
+    holder = _Holder(audio=Audio(data=b"world", format="wav"))
+    dumped = holder.model_dump(mode="json", by_alias=True)["audio"]
+    assert dumped["type"] == "audio"
+    assert dumped["mimeType"] == "audio/wav"
+    assert base64.b64decode(dumped["data"]) == b"world"
+
+
+@pytest.mark.anyio
+async def test_image_round_trips_through_stateless_http() -> None:
+    """Returning Image from a FastMCP tool must produce ImageContent on the wire,
+    end-to-end, in stateless HTTP mode with JSON responses (the configuration
+    required by remote MCP clients that cannot maintain session state)."""
+    mcp = FastMCP("test", host="0.0.0.0", stateless_http=True, json_response=True)
+
+    @mcp.tool()
+    def image_tool() -> Image:
+        return Image(data=b"hello", format="png")
+
+    app = mcp.streamable_http_app()
+    headers = {
+        "Accept": "application/json, text/event-stream",
+        "Content-Type": "application/json",
+    }
+
+    async with app.router.lifespan_context(app):
+        async with httpx.AsyncClient(
+            transport=httpx.ASGITransport(app=app),
+            base_url="http://127.0.0.1",
+            timeout=10.0,
+        ) as client:
+            initialize = await client.post(
+                "/mcp",
+                json={
+                    "jsonrpc": "2.0",
+                    "id": 1,
+                    "method": "initialize",
+                    "params": {
+                        "protocolVersion": "2025-06-18",
+                        "capabilities": {},
+                        "clientInfo": {"name": "test", "version": "1.0"},
+                    },
+                },
+                headers=headers,
+            )
+            assert initialize.status_code == 200
+
+            call = await client.post(
+                "/mcp",
+                json={
+                    "jsonrpc": "2.0",
+                    "id": 2,
+                    "method": "tools/call",
+                    "params": {"name": "image_tool", "arguments": {}},
+                },
+                headers=headers,
+            )
+
+    assert call.status_code == 200
+    body = call.json()
+    content = body["result"]["content"]
+    assert len(content) == 1
+    assert content[0]["type"] == "image"
+    assert content[0]["mimeType"] == "image/png"
+    assert base64.b64decode(content[0]["data"]) == b"hello"
+    assert body["result"]["isError"] is False