diff --git a/Pythonwin/pywin/framework/app.py b/Pythonwin/pywin/framework/app.py
index f0c4d6d3eb..4e0f09b943 100644
--- a/Pythonwin/pywin/framework/app.py
+++ b/Pythonwin/pywin/framework/app.py
@@ -3,9 +3,12 @@
 #
 # We also grab the FileOpen command, to invoke our Python editor
 " The PythonWin application code. Manages most aspects of MDI, etc "
+from __future__ import annotations
+
 import os
 import sys
 import traceback
+from typing import TYPE_CHECKING
 
 import regutil
 import win32api
@@ -16,6 +19,9 @@
 
 from . import scriptutils
 
+if TYPE_CHECKING:
+    from typing_extensions import Literal
+
 
 # Helper for writing a Window position by name, and later loading it.
 def SaveWindowSize(section, rect, state=""):
@@ -61,7 +67,7 @@ class MainFrame(window.MDIFrameWnd):
         win32ui.ID_INDICATOR_COLNUM,
     )
 
-    def OnCreate(self, cs):
+    def OnCreate(self, cs) -> Literal[-1, 0, 1]:
         self._CreateStatusBar()
         return 0
 
diff --git a/Pythonwin/pywin/tools/hierlist.py b/Pythonwin/pywin/tools/hierlist.py
index 7ec29563a6..1e4f8d7682 100644
--- a/Pythonwin/pywin/tools/hierlist.py
+++ b/Pythonwin/pywin/tools/hierlist.py
@@ -12,7 +12,7 @@
 # If you need to use the Tree Control, you may still find this API a reasonable
 # choice.  However, you should investigate using the tree control directly
 # to provide maximum flexibility (but with extra work).
-
+from __future__ import annotations
 
 import commctrl
 import win32api
@@ -259,7 +259,7 @@ def GetBitmapColumn(self, item):
         else:
             return 4
 
-    def GetSelectedBitmapColumn(self, item):
+    def GetSelectedBitmapColumn(self, item) -> int | None:
         return 0
 
     def CheckChangedChildren(self):
diff --git a/com/win32comext/axdebug/codecontainer.py b/com/win32comext/axdebug/codecontainer.py
index d82ee00089..babbd6fc4b 100644
--- a/com/win32comext/axdebug/codecontainer.py
+++ b/com/win32comext/axdebug/codecontainer.py
@@ -4,9 +4,12 @@
 to color the text, and also how to translate lines into offsets, and back.
 """
 
+from __future__ import annotations
+
 import os
 import sys
 import tokenize
+from typing import Any
 
 import win32api
 import winerror
@@ -26,7 +29,7 @@
 class SourceCodeContainer:
     def __init__(
         self,
-        text,
+        text: str | None,
         fileName="<Remove Me!>",
         sourceContext=0,
         startLineNumber=0,
@@ -34,12 +37,13 @@ def __init__(
         debugDocument=None,
     ):
         self.sourceContext = sourceContext  # The source context added by a smart host.
-        self.text = text
+        self.text: str | None = text
         if text:
             self._buildlines()
         self.nextLineNo = 0
         self.fileName = fileName
-        self.codeContexts = {}
+        # Any: PyIDispatch type is not statically exposed
+        self.codeContexts: dict[int, Any] = {}
         self.site = site
         self.startLineNumber = startLineNumber
         self.debugDocument = debugDocument
diff --git a/pyrightconfig.json b/pyrightconfig.json
index bc3c26fbc0..d90035dc31 100644
--- a/pyrightconfig.json
+++ b/pyrightconfig.json
@@ -37,6 +37,8 @@
   "reportOptionalIterable": "warning",
   "reportOptionalMemberAccess": "warning",
   "reportOptionalSubscript": "warning",
+  // Needs fixes in types-pywin32 and requires Python 3.8 to annotate ambiguous global variables
+  "reportUnnecessaryComparison": "warning",
   // TODO: Leave Unbound/Undefined to their own PR(s)
   "reportUnboundVariable": "warning",
   "reportUndefinedVariable": "warning",
@@ -49,8 +51,6 @@
   "reportMissingModuleSource": "none",
   // External type stubs may not be completable, and this will require type stubs for dynamic modules.
   "reportMissingTypeStubs": "information",
-  // Sometimes used for extra runtime safety
-  "reportUnnecessaryComparison": "warning",
   // Use Flake8/Pycln/Ruff instead
   "reportUnusedImport": "none",
 }
diff --git a/win32/Lib/sspi.py b/win32/Lib/sspi.py
index 5b62913543..d2658773ac 100644
--- a/win32/Lib/sspi.py
+++ b/win32/Lib/sspi.py
@@ -26,7 +26,7 @@ def __init__(self):
 
     def reset(self):
         """Reset everything to an unauthorized state"""
-        self.ctxt = None
+        self.ctxt: win32security.PyCtxtHandleType | None = None
         self.authenticated = False
         self.initiator_name = None
         self.service_name = None