diff --git a/.github/workflows/python-tests.yml b/.github/workflows/python-tests.yml
index 8d3619cc2..f5d08fbb1 100644
--- a/.github/workflows/python-tests.yml
+++ b/.github/workflows/python-tests.yml
@@ -28,8 +28,14 @@ on:
 
 jobs:
   test:
-    name: Run Python Tests
+    name: Run Python Tests (${{ matrix.python-version }})
     runs-on: ubuntu-latest
+    strategy:
+      fail-fast: false
+      matrix:
+        # 3.10 is the oldest supported version; 3.14 catches changes like the lazy
+        # __annotations__ evaluation from PEP 649.
+        python-version: ["3.10", "3.14"]
     steps:
       - name: Checkout repository
         uses: actions/checkout@v4
@@ -42,7 +48,7 @@ jobs:
           version: "latest"
 
       - name: Set up Python
-        run: uv python install 3.10
+        run: uv python install ${{ matrix.python-version }}
 
       - name: Install dependencies
         run: |
@@ -51,7 +57,7 @@ jobs:
           # re-resolving, so a dependency or version bump that forgot `uv lock` shows up here.
           # The dev extra is resolved in the lock too, so pytest runs against pinned versions
           # instead of whatever `uv pip install` would fetch today.
-          uv sync --locked --extra dev
+          uv sync --locked --extra dev --python ${{ matrix.python-version }}
 
       - name: Run tests with coverage
         run: |
@@ -65,7 +71,7 @@ jobs:
 
       - name: Upload coverage reports
         uses: codecov/codecov-action@v4
-        if: always()
+        if: always() && matrix.python-version == '3.10'
         # fail_ci_if_error: false does not cover a failed download: v4 crashes on the https
         # error before it reads that input. This job gates both release pipelines, and a
         # Codecov outage must not stop a release.
@@ -80,7 +86,7 @@ jobs:
         uses: actions/upload-artifact@v4
         if: always()
         with:
-          name: pytest-results
+          name: pytest-results-${{ matrix.python-version }}
           path: |
             Server/.pytest_cache/
             Server/tests/
diff --git a/Server/src/services/custom_tool_service.py b/Server/src/services/custom_tool_service.py
index f81b7c70e..a31d9de2c 100644
--- a/Server/src/services/custom_tool_service.py
+++ b/Server/src/services/custom_tool_service.py
@@ -409,7 +409,12 @@ async def _handler(ctx: Context, **kwargs) -> MCPResponse:
         _handler.__name__ = f"custom_tool_{definition.name}"
         _handler.__doc__ = definition.description or ""
         _handler.__signature__ = self._build_signature(definition)
-        _handler.__annotations__ = self._build_annotations(definition)
+        annotations = self._build_annotations(definition)
+        _handler.__annotations__ = annotations
+        # On Python 3.14, functools.wraps copies __annotate__ instead of __annotations__,
+        # and assigning __annotations__ sets __annotate__ to None. Without a real
+        # __annotate__ the logging/telemetry wrappers end up with no annotations.
+        _handler.__annotate__ = lambda format: dict(annotations)
         return _handler
 
     def _build_signature(self, definition: ToolDefinitionModel) -> inspect.Signature:
diff --git a/Server/tests/test_custom_tool_service_global_registration.py b/Server/tests/test_custom_tool_service_global_registration.py
new file mode 100644
index 000000000..4b9cb76c7
--- /dev/null
+++ b/Server/tests/test_custom_tool_service_global_registration.py
@@ -0,0 +1,44 @@
+import typing
+
+from models.models import ToolDefinitionModel, ToolParameterModel
+from services.custom_tool_service import CustomToolService
+
+
+class _RecordingMcp:
+    def __init__(self):
+        self.tools = {}
+
+    def custom_route(self, _path, methods=None):  # noqa: ARG002
+        def _decorator(fn):
+            return fn
+
+        return _decorator
+
+    def tool(self, name, description=None):  # noqa: ARG002
+        def _decorator(fn):
+            self.tools[name] = fn
+            return fn
+
+        return _decorator
+
+
+def test_global_tool_keeps_parameter_annotations_through_wrappers():
+    """FastMCP builds the tool schema from the registered function's type hints. If the
+    logging/telemetry wrappers lose them (Python 3.14), pydantic raises KeyError and
+    the tool is dropped."""
+    mcp = _RecordingMcp()
+    service = CustomToolService(mcp)
+    definition = ToolDefinitionModel(
+        name="my_tool",
+        description="My tool",
+        parameters=[
+            ToolParameterModel(name="action", type="string"),
+            ToolParameterModel(name="count", type="integer", required=False, default_value="3"),
+        ],
+    )
+
+    service.register_global_tools([definition])
+
+    hints = typing.get_type_hints(mcp.tools["my_tool"])
+    assert hints["action"] is str
+    assert hints["count"] is int
diff --git a/website/docs/contributing/dev-setup.md b/website/docs/contributing/dev-setup.md
index 6cd8fb3fa..875bd7169 100644
--- a/website/docs/contributing/dev-setup.md
+++ b/website/docs/contributing/dev-setup.md
@@ -256,7 +256,7 @@ GitHub withholds repository secrets from workflow runs triggered by a fork's pul
 | Check | On a fork PR |
 |---|---|
 | `Compile MCPForUnity (win/osx/linux)` | **Runs.** License-free compile across win/osx/linux — real signal. |
-| `Run Python Tests` | **Runs.** Real signal. |
+| `Run Python Tests (3.10/3.14)` | **Runs.** Real signal. |
 | `Check docs reference is fresh` | **Runs.** Real signal. |
 | `Test in editmode on Unity <version>` | **Skipped** — no Editor booted, no C# compiled by this job. |
 | `e2e-bridge` | **Skipped** — no Editor booted, no tool call exercised. |
diff --git a/website/docs/contributing/testing.md b/website/docs/contributing/testing.md
index 2cdcd3e34..cab547864 100644
--- a/website/docs/contributing/testing.md
+++ b/website/docs/contributing/testing.md
@@ -25,7 +25,7 @@ cd Server && uv run pytest tests/test_manage_material.py -v
 cd Server && uv run pytest tests/ -k "test_create_material" -v
 ```
 
-CI workflow: `.github/workflows/python-tests.yml`. Coverage is uploaded to Codecov on every run.
+CI workflow: `.github/workflows/python-tests.yml`. It runs the tests on Python 3.10 and 3.14; coverage is uploaded to Codecov from the 3.10 job.
 
 ### Adding a Python test