diff --git a/extensions/positron-python/pythonFiles/positron/inspectors.py b/extensions/positron-python/pythonFiles/positron/inspectors.py
index a91c1db0c8e..2c542d6b7e2 100644
--- a/extensions/positron-python/pythonFiles/positron/inspectors.py
+++ b/extensions/positron-python/pythonFiles/positron/inspectors.py
@@ -13,15 +13,9 @@
 import types
 import uuid
 from abc import ABC, abstractmethod
-from collections.abc import (
-    Mapping,
-    MutableMapping,
-    MutableSequence,
-    MutableSet,
-    Sequence,
-    Set,
-)
+from collections.abc import Mapping, MutableMapping, MutableSequence, MutableSet, Sequence, Set
 from typing import (
+    TYPE_CHECKING,
     Any,
     Callable,
     Collection,
@@ -35,7 +29,6 @@
     Protocol,
     Sized,
     Tuple,
-    TYPE_CHECKING,
     Type,
     TypeVar,
     Union,
@@ -567,7 +560,7 @@ def copy(self, value: torch.Tensor) -> torch.Tensor:
 
 
 class _BaseMapInspector(PositronInspector[MT], ABC):
-    def get_kind(self, value: Mapping) -> str:
+    def get_kind(self, value: MT) -> str:
         return "map"
 
     @abstractmethod
diff --git a/extensions/positron-python/pythonFiles/positron/positron_ipkernel.py b/extensions/positron-python/pythonFiles/positron/positron_ipkernel.py
index cba006c025b..6efbcf66fc7 100644
--- a/extensions/positron-python/pythonFiles/positron/positron_ipkernel.py
+++ b/extensions/positron-python/pythonFiles/positron/positron_ipkernel.py
@@ -4,32 +4,32 @@
 
 """ Positron extensions to the iPython Kernel."""
 from __future__ import annotations
+
 import asyncio
 import logging
 import warnings
 from collections.abc import Iterable
 from itertools import chain
-from typing import Any, Callable, Container, Dict, Mapping, Optional, Set, Tuple, Type
+from typing import Any, Callable, Container, Coroutine, Dict, Mapping, Optional, Set, Tuple, Type
 
+import traitlets
 from ipykernel.comm.manager import CommManager
 from ipykernel.ipkernel import IPythonKernel
 from ipykernel.kernelapp import IPKernelApp
-from ipykernel.zmqshell import ZMQInteractiveShell, ZMQDisplayPublisher
-from IPython.core import oinspect
+from ipykernel.zmqshell import ZMQDisplayPublisher, ZMQInteractiveShell
+from IPython.core import oinspect, page
 from IPython.core.interactiveshell import InteractiveShell
-from IPython.core.magic import Magics, line_magic, magics_class, needs_local_scope, MagicsManager
-from IPython.core import page
+from IPython.core.magic import Magics, MagicsManager, line_magic, magics_class, needs_local_scope
 from IPython.utils import PyColorize
-import traitlets
 
 from .dataviewer import DataViewerService
-from .variables import VariablesService
 from .frontend import FrontendService
 from .help import HelpService
 from .inspectors import get_inspector
 from .lsp import LSPService
 from .plots import PositronDisplayPublisherHook
 from .utils import cancel_tasks, create_task
+from .variables import VariablesService
 
 POSITRON_DATA_VIEWER_COMM = "positron.dataViewer"
 """The comm channel target_name for Positron's Data Viewer"""
@@ -69,12 +69,11 @@ class PositronIPythonInspector(oinspect.Inspector):
     def pinfo(
         self,
         obj: Any,
-        oname: str,
-        formatter: Callable[[str], Dict[str, str]],
-        info: oinspect.OInfo,
-        *,
-        detail_level: int,
-        enable_html_pager: bool,
+        oname: str = "",
+        formatter: Optional[Callable[[str], Dict[str, str]]] = None,
+        info: Optional[oinspect.OInfo] = None,
+        detail_level: int = 0,
+        enable_html_pager: bool = True,
         omit_sections: Container[str] = (),
     ) -> None:
         # Intercept `%pinfo obj` / `obj?` calls, and instead use Positron's help service
@@ -106,7 +105,7 @@ class PositronShell(ZMQInteractiveShell):
     ).tag(config=True)
 
     @traitlets.observe("colors")
-    def init_inspector(self, change: Optional[traitlets.Bunch] = None) -> None:
+    def init_inspector(self, changes: Optional[traitlets.Bunch] = None) -> None:
         # Override to pass `parent=self` to the inspector
         self.inspector = self.inspector_class(
             oinspect.InspectColors,
@@ -160,7 +159,6 @@ class PositronIPyKernel(IPythonKernel):
 
     shell: PositronShell
     comm_manager: CommManager
-    execution_count: int
 
     shell_class: PositronShell = traitlets.Type(PositronShell, klass=InteractiveShell)  # type: ignore
 
@@ -230,7 +228,7 @@ def start(self) -> None:
         super().start()
         self.help_service.start()
 
-    async def do_shutdown(self, restart: bool) -> Dict[str, Any]:
+    async def do_shutdown(self, restart: bool) -> Dict[str, str | bool]:  # type: ignore ReportIncompatibleMethodOverride
         """
         Handle kernel shutdown.
         """
diff --git a/extensions/positron-python/pythonFiles/positron/positron_jedilsp.py b/extensions/positron-python/pythonFiles/positron/positron_jedilsp.py
index d2db1f6ab72..2b8949062aa 100644
--- a/extensions/positron-python/pythonFiles/positron/positron_jedilsp.py
+++ b/extensions/positron-python/pythonFiles/positron/positron_jedilsp.py
@@ -122,7 +122,7 @@ class HelpTopicRequest:
 
 
 class PositronJediLanguageServerProtocol(JediLanguageServerProtocol):
-    def get_message_type(self, method: str) -> Optional[Type]:
+    def get_message_type(self, method: str) -> Optional[Type]:  # type: ignore
         # Overriden to include custom Positron LSP messages.
         # Doing so ensures that the corresponding feature function receives `params` of the correct type.
         if method == _HELP_TOPIC:
@@ -137,7 +137,7 @@ def __init__(self, *args: Any, **kwargs: Any) -> None:
         super().__init__(*args, **kwargs)
 
         self.loop: asyncio.AbstractEventLoop
-        self.lsp: PositronJediLanguageServerProtocol
+        self.lsp: PositronJediLanguageServerProtocol  # type: ignore reportIncompatibleVariableOverride
 
         # LSP comm used to notify the frontend when the server is ready
         self._comm: Optional[BaseComm] = None
@@ -363,7 +363,7 @@ def positron_completion(
         has_whitespace = " " in trimmed_line
         if server.kernel is not None and not (is_completing_attribute or has_whitespace):
             # Cast type from traitlets.Dict to typing.Dict
-            magic_commands = cast(Dict[str, Callable], server.kernel.shell.magics_manager.lsmagic())
+            magic_commands = cast(Dict[str, Any], server.kernel.shell.magics_manager.lsmagic())
 
             chars_before_cursor = trimmed_line[: params.position.character]
 
diff --git a/extensions/positron-python/pythonFiles/positron/pydoc.py b/extensions/positron-python/pythonFiles/positron/pydoc.py
index c1bbec6b2c6..92638f9787e 100644
--- a/extensions/positron-python/pythonFiles/positron/pydoc.py
+++ b/extensions/positron-python/pythonFiles/positron/pydoc.py
@@ -218,7 +218,7 @@ def page(self, title, contents):
         )
         # --- End Positron ---
 
-    def heading(self, title: str, extras="") -> str:
+    def heading(self, title: str, extras="") -> str:  # type: ignore ReportIncompatibleMethodOverride
         """Format a page heading."""
         # Simplified version of pydoc.HTMLDoc.heading that doesn't use tables
         lines = [f"<h1>{title}</h1>"]
@@ -227,7 +227,7 @@ def heading(self, title: str, extras="") -> str:
         result = "\n".join(lines)
         return result
 
-    def section(
+    def section(  # type: ignore
         self,
         title: str,
         cls: str,
@@ -236,7 +236,7 @@ def section(
         prelude="",
         marginalia=None,
         gap=None,
-    ) -> str:
+    ) -> str:  # type: ignore ReportIncompatibleMethodOverride
         """Format a section with a heading."""
         # Simplified version of pydoc.HTMLDoc.section that doesn't use tables
         if width is not None:
@@ -264,7 +264,7 @@ def bigsection(self, *args):
         return self.section(*args)
 
     # Heavily customized version of pydoc.HTMLDoc.docmodule
-    def docmodule(self, object: ModuleType, *_):
+    def docmodule(self, object: ModuleType, *_):  # type: ignore reportIncompatibleMethodOverride
         obj_name = object.__name__
 
         # Create the heading, with links to each parent module
@@ -338,7 +338,7 @@ def docmodule(self, object: ModuleType, *_):
         return result
 
     # Heavily customized version of pydoc.HTMLDoc.docclass
-    def docclass(self, obj: Type, name=None, *_):
+    def docclass(self, obj: Type, name=None, *_):  # type: ignore reportIncompatibleMethodOverride
         obj_name = name or obj.__name__
 
         # Separate the class's members into attributes and methods
@@ -497,7 +497,7 @@ def markup(self, text, escape=None, funcs={}, classes={}, methods={}):
         return text
 
     # as is from pydoc.HTMLDoc to port Python 3.11 breaking CSS changes
-    def index(self, dir, shadowed: Optional[Dict[str, int]] = None):
+    def index(self, dir, shadowed: Optional[Dict[str, int]] = None):  # type: ignore reportIncompatibleMethodOverride
         """Generate an HTML index for a directory of modules."""
         modpkgs = []
         if shadowed is None:
diff --git a/extensions/positron-python/pythonFiles/tests/positron/conftest.py b/extensions/positron-python/pythonFiles/tests/positron/conftest.py
index cc66e02a454..8d32aa35293 100644
--- a/extensions/positron-python/pythonFiles/tests/positron/conftest.py
+++ b/extensions/positron-python/pythonFiles/tests/positron/conftest.py
@@ -4,7 +4,6 @@
 import pytest
 from IPython.conftest import get_ipython
 from IPython.terminal.interactiveshell import TerminalInteractiveShell
-
 from positron.positron_ipkernel import PositronIPyKernel
 
 
@@ -17,7 +16,7 @@ def __init__(self, *args, **kwargs):
         self.messages = []
         super().__init__(*args, **kwargs)
 
-    def publish_msg(self, msg_type, **msg):
+    def publish_msg(self, msg_type, **msg):  # type: ignore ReportIncompatibleMethodOverride
         msg["msg_type"] = msg_type
         self.messages.append(msg)
 
diff --git a/extensions/positron-python/pythonFiles/tests/positron/test_plots.py b/extensions/positron-python/pythonFiles/tests/positron/test_plots.py
index a8900c12e8e..2af341473d4 100644
--- a/extensions/positron-python/pythonFiles/tests/positron/test_plots.py
+++ b/extensions/positron-python/pythonFiles/tests/positron/test_plots.py
@@ -1,22 +1,21 @@
 import codecs
 import pickle
 from pathlib import Path
-from typing import cast, Iterable
+from typing import Iterable, cast
 
 import matplotlib
 import matplotlib.pyplot as plt
 import pytest
 from IPython.conftest import get_ipython
 from IPython.core.formatters import DisplayFormatter
+from matplotlib.axes import Axes
 from matplotlib.figure import Figure
 from matplotlib.testing.compare import compare_images
 from matplotlib_inline.backend_inline import configure_inline_support
-
 from positron.plots import BASE_DPI, PositronDisplayPublisherHook
 
 from .conftest import DummyComm
 
-
 PLOT_DATA = [1, 2]
 
 
@@ -113,8 +112,9 @@ def test_hook_call(hook: PositronDisplayPublisherHook, images_path: Path) -> Non
     fig.savefig(str(actual))
 
     # Create the reference figure
-    fig_ref: plt.figure.Figure = plt.figure()
-    fig_ref.subplots().plot(PLOT_DATA)
+    fig_ref = cast(Figure, plt.figure())
+    fig_axes = cast(Axes, fig_ref.subplots())
+    fig_axes.plot(PLOT_DATA)
     expected = images_path / "test-hook-call-expected.png"
     fig_ref.savefig(str(expected))
 
@@ -210,8 +210,9 @@ def test_hook_render(figure_comm: DummyComm, images_path: Path) -> None:
     width_in = width_px / BASE_DPI
     height_in = height_px / BASE_DPI
 
-    fig_ref: plt.figure.Figure = plt.figure()
-    fig_ref.subplots().plot([1, 2])
+    fig_ref = cast(Figure, plt.figure())
+    fig_axes = cast(Axes, fig_ref.subplots())
+    fig_axes.plot([1, 2])
     fig_ref.set_dpi(dpi)
     fig_ref.set_size_inches(width_in, height_in)
 
diff --git a/extensions/positron-python/pythonFiles/tests/test_create_venv.py b/extensions/positron-python/pythonFiles/tests/test_create_venv.py
index 772fc02708f..350fa5ca997 100644
--- a/extensions/positron-python/pythonFiles/tests/test_create_venv.py
+++ b/extensions/positron-python/pythonFiles/tests/test_create_venv.py
@@ -242,7 +242,7 @@ def redirect_io(stream: str, new_stream):
 class CustomIO(io.TextIOWrapper):
     """Custom stream object to replace stdio."""
 
-    name: str = "customio"
+    name: str = "customio"  # type: ignore ReportIncompatibleMethodOverride  (remove once updated upstream)
 
     def __init__(self, name: str, encoding="utf-8", newline=None):
         self._buffer = io.BytesIO()
diff --git a/extensions/positron-python/pythonFiles/vscode_pytest/__init__.py b/extensions/positron-python/pythonFiles/vscode_pytest/__init__.py
index 6f5687357f1..8d585c35963 100644
--- a/extensions/positron-python/pythonFiles/vscode_pytest/__init__.py
+++ b/extensions/positron-python/pythonFiles/vscode_pytest/__init__.py
@@ -689,7 +689,7 @@ def post_response(cwd: str, session_node: TestNode) -> None:
 class PathEncoder(json.JSONEncoder):
     """A custom JSON encoder that encodes pathlib.Path objects as strings."""
 
-    def default(self, obj):
+    def default(self, obj):  # type: ignore ReportIncompatibleMethodOverride (remove once updated upstream)
         if isinstance(obj, pathlib.Path):
             return os.fspath(obj)
         return super().default(obj)