diff --git a/docs/advanced/extensions.md b/docs/advanced/extensions.md
index e8793b8cb1..876cabee33 100644
--- a/docs/advanced/extensions.md
+++ b/docs/advanced/extensions.md
@@ -25,9 +25,11 @@ Done. The server now advertises `io.modelcontextprotocol/ui` under
     Extensions are fixed at construction. There is no `add_extension` to call later:
     a server's capability map should not change while clients are connected to it.
 
-The capability map rides `server/discover`, which is a **2026-07-28** path. A legacy
-`initialize` handshake has nowhere to put it, so a legacy client simply doesn't see
-the extension. Design for that: an extension *augments* a server, it must not be the
+The capability map rides `server/discover` on **2026-07-28** connections and the
+`initialize` handshake on **2025-11-25 and earlier** connections. Both client and
+server advertisements preserve `capabilities.extensions`, including extension
+settings, on every supported legacy version. Peers that do not support an extension
+can ignore its advertisement: an extension *augments* a server, it must not be the
 only way the server is usable.
 
 ## Writing your own
diff --git a/scripts/gen_surface_types.py b/scripts/gen_surface_types.py
index d77eedc480..4eca31f4df 100644
--- a/scripts/gen_surface_types.py
+++ b/scripts/gen_surface_types.py
@@ -3,8 +3,8 @@
 Runs `datamodel-code-generator` over each `schema/PINNED.json` entry and
 writes the result to `src/mcp-types/mcp_types/_v<version>/__init__.py` (the
 underscore marks these as internal validators, not public API) with only
-the fixes the raw output needs: a small JSON pre-patch for the known
-`number`-as-`integer` schema.json defect, a header, full URLs for the spec's
+the fixes the raw output needs: JSON pre-patches for schema defects and legacy
+extension advertisements, a header, full URLs for the spec's
 site-absolute doc links, plain type aliases, and per-version epilogue aliases. Run with
 `uv run --frozen --group codegen python scripts/gen_surface_types.py [--check]`.
 """
@@ -239,6 +239,17 @@ def build(entry: dict[str, str]) -> str:
     version = entry["protocol_version"]
     schema = json.loads((SCHEMA_DIR / f"{version}.json").read_text(encoding="utf-8"))
     patch_schema(schema, SCHEMA_PATCHES.get(version, []))
+    if version == "2025-11-25":
+        # Extensions predate their formal 2026 field; legacy peers negotiate them
+        # through initialize (modelcontextprotocol/modelcontextprotocol#3364).
+        for role in ("Client", "Server"):
+            properties = schema["$defs"][f"{role}Capabilities"]["properties"]
+            assert "extensions" not in properties
+            properties["extensions"] = {
+                "type": "object",
+                "additionalProperties": {"type": "object", "additionalProperties": True},
+                "description": f"MCP extensions that the {role.lower()} supports, including on legacy connections.",
+            }
     make_server_info_opaque(schema)
     if "JSONValue" in schema["$defs"]:
         # A single recursive alias avoids mutually recursive alias evaluation in type checkers.
diff --git a/src/mcp-types/mcp_types/_types.py b/src/mcp-types/mcp_types/_types.py
index e91fdcc3b9..645a53f1e2 100644
--- a/src/mcp-types/mcp_types/_types.py
+++ b/src/mcp-types/mcp_types/_types.py
@@ -405,7 +405,7 @@ class ClientCapabilities(MCPModel):
     roots: RootsCapability | None = None
     """Present if the client supports listing roots."""
     extensions: dict[str, dict[str, Any]] | None = None
-    """MCP extensions the client supports (2026-07-28). Keys are extension
+    """MCP extensions the client supports, including on legacy connections. Keys are extension
     identifiers; values are per-extension settings (empty object = no settings)."""
     tasks: ClientTasksCapability | None = None
     """Present if the client supports task-augmented requests (2025-11-25 only)."""
@@ -505,7 +505,7 @@ class ServerCapabilities(MCPModel):
     """Present if the server offers autocompletion suggestions for prompts and resources."""
 
     extensions: dict[str, dict[str, Any]] | None = None
-    """MCP extensions the server supports (2026-07-28). Keys are extension
+    """MCP extensions the server supports, including on legacy connections. Keys are extension
     identifiers; values are per-extension settings (empty object = no settings)."""
 
     tasks: ServerTasksCapability | None = None
diff --git a/src/mcp-types/mcp_types/_v2025_11_25/__init__.py b/src/mcp-types/mcp_types/_v2025_11_25/__init__.py
index 5ffd15f0ec..8d5b00b28c 100644
--- a/src/mcp-types/mcp_types/_v2025_11_25/__init__.py
+++ b/src/mcp-types/mcp_types/_v2025_11_25/__init__.py
@@ -218,6 +218,10 @@ class ClientCapabilities(WireModel):
     """
     Present if the client supports task-augmented requests.
     """
+    extensions: dict[str, dict[str, Any]] | None = None
+    """
+    MCP extensions that the client supports, including on legacy connections.
+    """
 
 
 class Argument(WireModel):
@@ -1132,6 +1136,10 @@ class ServerCapabilities(WireModel):
     """
     Present if the server offers any tools to call.
     """
+    extensions: dict[str, dict[str, Any]] | None = None
+    """
+    MCP extensions that the server supports, including on legacy connections.
+    """
 
 
 class SetLevelRequestParams(WireModel):
diff --git a/tests/client/test_client.py b/tests/client/test_client.py
index c63248798e..b8e56a1ec7 100644
--- a/tests/client/test_client.py
+++ b/tests/client/test_client.py
@@ -117,6 +117,7 @@ async def test_client_is_initialized(app: MCPServer):
                 prompts=PromptsCapability(list_changed=False),
                 resources=ResourcesCapability(subscribe=False, list_changed=False),
                 tools=ToolsCapability(list_changed=False),
+                extensions={},
             )
         )
         assert client.server_info is not None
diff --git a/tests/interaction/lowlevel/test_initialize.py b/tests/interaction/lowlevel/test_initialize.py
index 1ebc9e2681..82b755741f 100644
--- a/tests/interaction/lowlevel/test_initialize.py
+++ b/tests/interaction/lowlevel/test_initialize.py
@@ -147,6 +147,7 @@ async def completion(ctx: ServerRequestContext, params: types.CompleteRequestPar
             resources=ResourcesCapability(subscribe=True, list_changed=False),
             tools=ToolsCapability(list_changed=False),
             completions=CompletionsCapability(),
+            extensions={},
         )
     )
 
@@ -157,7 +158,7 @@ async def test_initialize_minimal_server_advertises_no_capabilities(connect: Con
     async with connect(Server("bare")) as client:
         capabilities = client.server_capabilities
 
-    assert capabilities == snapshot(ServerCapabilities())
+    assert capabilities == snapshot(ServerCapabilities(extensions={}))
 
 
 @requirement("lifecycle:initialize:client-info")
diff --git a/tests/server/mcpserver/test_extension.py b/tests/server/mcpserver/test_extension.py
index 5aa05b1e3d..f7d6da163a 100644
--- a/tests/server/mcpserver/test_extension.py
+++ b/tests/server/mcpserver/test_extension.py
@@ -176,14 +176,13 @@ async def test_extension_settings_advertised_under_server_capabilities() -> None
     assert extensions == snapshot({"com.example/settings": {"feature": {"enabled": True}}})
 
 
-async def test_extension_settings_dropped_on_legacy_handshake() -> None:
-    """Pinned gap: the 2025 `ServerCapabilities` wire schema has no `extensions`
-    field, so a legacy `initialize` handshake drops the advertised extension even
-    though the modern `auto` path carries it."""
-    server = MCPServer("test", extensions=[_SettingsExt()])
+async def test_extension_settings_preserved_on_legacy_handshake() -> None:
+    """SDK compatibility: a legacy initialize handshake preserves nested extension settings."""
+    extension = _SettingsExt()
+    server = MCPServer("test", extensions=[extension])
 
     async with Client(server, mode="legacy") as client:
-        assert client.server_capabilities.extensions is None
+        assert client.server_capabilities.extensions == {extension.identifier: extension.settings()}
 
 
 def test_duplicate_extension_identifier_raises() -> None:
diff --git a/tests/server/test_apps.py b/tests/server/test_apps.py
index 8d8bf74b74..89f00268b9 100644
--- a/tests/server/test_apps.py
+++ b/tests/server/test_apps.py
@@ -83,12 +83,10 @@ async def test_auto_mode_carries_apps_extension_under_server_capabilities() -> N
         assert client.server_capabilities.extensions == snapshot({"io.modelcontextprotocol/ui": {}})
 
 
-async def test_legacy_handshake_drops_apps_extension_from_capabilities() -> None:
-    """Pinned gap: the 2025 `ServerCapabilities` wire schema has no `extensions` field,
-    so a `mode='legacy'` handshake cannot carry the Apps capability -- only `mode='auto'`
-    (server/discover) does. This pins the divergence rather than fixing it."""
+async def test_legacy_handshake_carries_apps_extension_in_capabilities() -> None:
+    """SDK compatibility: a legacy initialize handshake advertises MCP Apps with empty settings."""
     async with Client(_clock_server(), mode="legacy") as client:
-        assert client.server_capabilities.extensions is None
+        assert client.server_capabilities.extensions == {EXTENSION_ID: {}}
 
 
 async def test_apps_tool_returns_rich_output_when_client_negotiated_apps() -> None:
diff --git a/tests/server/test_extensions_capability.py b/tests/server/test_extensions_capability.py
index 49c81f58f4..bc6b243224 100644
--- a/tests/server/test_extensions_capability.py
+++ b/tests/server/test_extensions_capability.py
@@ -56,16 +56,16 @@ async def test_modern_connection_carries_the_advertised_extensions_map() -> None
         assert client.server_capabilities.extensions == snapshot({"com.example/x": {"k": 1}})
 
 
-async def test_legacy_handshake_drops_the_extensions_map() -> None:
-    """Pinned gap: the handshake-era `initialize` result is serialized against the
-    2025 wire schema, which has no `extensions` field, so a legacy handshake cannot
-    carry it; the client sees `None` even though the server advertised one."""
-    server = MCPServer("host", extensions=[_Extension()])
+async def test_legacy_handshake_carries_the_extensions_map() -> None:
+    """SDK compatibility: a legacy initialize handshake preserves the server's extension settings."""
+    extension = _Extension()
+    server = MCPServer("host", extensions=[extension])
     async with Client(server, mode="legacy") as client:
-        assert client.server_capabilities.extensions is None
+        assert client.server_capabilities.extensions == {extension.identifier: extension.settings()}
 
 
-async def test_server_accepts_capability_for_client_advertised_extension() -> None:
+@pytest.mark.parametrize("mode", ["auto", "legacy"])
+async def test_server_accepts_capability_for_client_advertised_extension(mode: str) -> None:
     """SDK-defined: a client advertising `extensions={id: ...}` makes the
     server-side `check_client_capability` return True when queried for that id.
     Observed inside a tool handler."""
@@ -83,7 +83,7 @@ async def list_tools(
         return types.ListToolsResult(tools=[types.Tool(name="probe", input_schema={"type": "object"})])
 
     server = Server("checker", on_call_tool=call_tool, on_list_tools=list_tools)
-    async with Client(server, extensions=[advertise(_EXTENSION_ID, {"mimeTypes": ["text/html"]})]) as client:
+    async with Client(server, mode=mode, extensions=[advertise(_EXTENSION_ID, {"mimeTypes": ["text/html"]})]) as client:
         await client.call_tool("probe", {})
 
     assert supported == [True]
diff --git a/tests/types/test_methods.py b/tests/types/test_methods.py
index e93346b134..b9a6092756 100644
--- a/tests/types/test_methods.py
+++ b/tests/types/test_methods.py
@@ -11,7 +11,7 @@
 import pydantic
 import pytest
 from mcp_types import methods
-from mcp_types.version import KNOWN_PROTOCOL_VERSIONS
+from mcp_types.version import HANDSHAKE_PROTOCOL_VERSIONS, KNOWN_PROTOCOL_VERSIONS
 from pydantic import BaseModel
 
 # Transcribed from each schema's ClientRequest/ServerRequest/ClientNotification/
@@ -470,6 +470,74 @@ def test_discovery_capabilities_preserve_nested_json_values() -> None:
     assert methods.serialize_server_result("server/discover", "2026-07-28", raw) == raw
 
 
+@pytest.mark.parametrize("version", HANDSHAKE_PROTOCOL_VERSIONS)
+@pytest.mark.parametrize(
+    "extensions",
+    [
+        {},
+        {"io.modelcontextprotocol/ui": {}},
+        {"com.example/settings": {"nested": [None, True, 1, 1.5, "text", {"child": [False]}]}},
+    ],
+)
+def test_initialize_round_trip_preserves_server_extensions(version: str, extensions: dict[str, dict[str, Any]]) -> None:
+    """SDK compatibility: legacy initialize responses carry extension advertisements, including opaque settings."""
+    raw = {
+        "protocolVersion": version,
+        "capabilities": {"tools": {}, "extensions": extensions},
+        "serverInfo": {"name": "server", "version": "1"},
+    }
+    serialized = methods.serialize_server_result("initialize", version, raw)
+    assert serialized == raw
+    parsed = methods.parse_server_result("initialize", version, serialized)
+    assert isinstance(parsed, types.InitializeResult)
+    assert parsed.capabilities.extensions == extensions
+
+
+@pytest.mark.parametrize("version", HANDSHAKE_PROTOCOL_VERSIONS)
+@pytest.mark.parametrize(
+    "extensions",
+    [
+        {},
+        {"io.modelcontextprotocol/ui": {}},
+        {"com.example/settings": {"nested": [None, True, 1, 1.5, "text", {"child": [False]}]}},
+    ],
+)
+def test_initialize_round_trip_preserves_client_extensions(version: str, extensions: dict[str, dict[str, Any]]) -> None:
+    """SDK compatibility: the legacy request wire model preserves the same extension settings as the public parser."""
+    raw = {
+        "jsonrpc": "2.0",
+        "id": 1,
+        "method": "initialize",
+        "params": {
+            "protocolVersion": version,
+            "capabilities": {"extensions": extensions},
+            "clientInfo": {"name": "client", "version": "1"},
+        },
+    }
+    surface = methods.CLIENT_REQUESTS[("initialize", version)]
+    serialized = surface.model_validate(raw).model_dump(by_alias=True, mode="json", exclude_none=True)
+    assert serialized == raw
+    parsed = methods.parse_client_request("initialize", version, serialized["params"])
+    assert isinstance(parsed, types.InitializeRequest)
+    assert parsed.params.capabilities.extensions == extensions
+
+
+@pytest.mark.parametrize("version", HANDSHAKE_PROTOCOL_VERSIONS)
+@pytest.mark.parametrize("capabilities", [{}, {"extensions": None}])
+def test_initialize_omits_unset_server_extensions(version: str, capabilities: dict[str, Any]) -> None:
+    """SDK-defined: absent or null extension advertisements remain omitted on the legacy wire."""
+    raw = {
+        "protocolVersion": version,
+        "capabilities": capabilities,
+        "serverInfo": {"name": "server", "version": "1"},
+    }
+    serialized = methods.serialize_server_result("initialize", version, raw)
+    assert serialized == {**raw, "capabilities": {}}
+    parsed = methods.parse_server_result("initialize", version, serialized)
+    assert isinstance(parsed, types.InitializeResult)
+    assert parsed.capabilities.extensions is None
+
+
 def test_elicit_request_surface_accepts_loose_property_schemas():
     """Older python-sdk emits `anyOf` for `Optional` form fields; the surface gate must let it through."""
     params = {