diff --git a/AutoDuck/document_object.py b/AutoDuck/document_object.py
index 9d9139699d..82be3a8a21 100644
--- a/AutoDuck/document_object.py
+++ b/AutoDuck/document_object.py
@@ -73,6 +73,8 @@ def GetDocument(fname="pywin32-document.xml"):
     handler = categoryHandler()
     parser.setContentHandler(handler)
     parser.parse(fname)
+    if handler.document is None:
+        raise RuntimeError("document was not set by parser")
     return handler.document
 
 
diff --git a/adodbapi/adodbapi.py b/adodbapi/adodbapi.py
index cbc0c0f0e1..38426b4613 100644
--- a/adodbapi/adodbapi.py
+++ b/adodbapi/adodbapi.py
@@ -27,6 +27,8 @@
 or CPython 3.4 or later.
 """
 
+from __future__ import annotations
+
 __version__ = "2.6.2.0"
 version = "adodbapi v" + __version__
 
@@ -35,6 +37,8 @@
 import os
 import sys
 import weakref
+from collections.abc import Callable, Mapping
+from typing import NoReturn
 
 from . import ado_consts as adc, apibase as api, process_connect_string
 
@@ -59,9 +63,6 @@ def getIndexedValue(obj, index):
     return obj(index)
 
 
-from collections.abc import Mapping
-
-
 # -----------------  The .connect method -----------------
 def make_COM_connecter():
     try:
@@ -238,7 +239,9 @@ def __init__(self):  # now define the instance attributes
         self.cursors = weakref.WeakValueDictionary[int, Cursor]()
         self.dbms_name = ""
         self.dbms_version = ""
-        self.errorhandler = None  # use the standard error handler for this instance
+        self.errorhandler: (
+            Callable[[Connection, Cursor, type[api.Error], object], NoReturn] | None
+        ) = None  # use the standard error handler for this instance
         self.transaction_level = 0  # 0 == Not in a transaction, at the top level
         self._autocommit = False
 
@@ -401,6 +404,9 @@ def _rollback(self):
             except Exception as e:
                 self._raiseConnectionError(api.ProgrammingError, e)
 
+    # TODO: Use a property+setter instead
+    variantConversions: api.MultiMap
+
     def __setattr__(self, name, value):
         if name == "autocommit":  # extension: allow user to turn autocommit on or off
             if self.supportsTransactions:
@@ -542,17 +548,21 @@ class Cursor:
     ## errorhandler...
     ##   allows the programmer to override the connection's default error handler
 
-    def __init__(self, connection):
+    def __init__(self, connection: Connection):
         self.command = None
         self._ado_prepared = False
-        self.messages = []
+        self.messages: list[tuple[type[api.Error], object]] = []
         self.connection = connection
-        self.paramstyle = connection.paramstyle  # used for overriding the paramstyle
-        self._parameter_names = []
+        self.paramstyle = connection.paramstyle
+        """Used for overriding the paramstyle"""
+        self._parameter_names: list[str] = []
         self.recordset_is_remote = False
-        self.rs = None  # the ADO recordset for this cursor
-        self.converters = []  # conversion function for each column
-        self.columnNames = {}  # names of columns {lowercase name : number,...}
+        self.rs = None
+        """The ADO recordset for this cursor"""
+        self.converters: list[Callable[[object], object]] = []
+        """Conversion function for each column"""
+        self.columnNames: dict[str, int] = {}
+        """Names of columns {lowercase name : number,...}"""
         self.numberOfColumns = 0
         self._description = None
         self.rowcount = -1
@@ -587,7 +597,9 @@ def __exit__(self, exc_type, exc_val, exc_tb):
         "Allow database cursors to be used with context managers."
         self.close()
 
-    def _raiseCursorError(self, errorclass, errorvalue):
+    def _raiseCursorError(
+        self, errorclass: type[api.Error], errorvalue: object
+    ) -> NoReturn:
         eh = self.errorhandler
         if eh is None:
             eh = api.standardErrorHandler
@@ -613,9 +625,8 @@ def build_column_info(self, recordset):
         for i in range(self.numberOfColumns):
             f = getIndexedValue(self.rs.Fields, i)
             try:
-                self.converters.append(
-                    varCon[f.Type]
-                )  # conversion function for this column
+                # conversion function for this column
+                self.converters.append(varCon[f.Type])
             except KeyError:
                 self._raiseCursorError(
                     api.InternalError, "Data column of Unknown ADO type=%s" % f.Type
@@ -716,7 +727,7 @@ def _new_command(self, command_type=adc.adCmdText):
 
         if self.connection is None:
             self._raiseCursorError(api.InterfaceError, None)
-            return
+            return  # Still return in case a custom errorHandler doesn't raise
         try:
             self.cmd = Dispatch("ADODB.Command")
             self.cmd.ActiveConnection = self.connection.connector
@@ -1036,7 +1047,7 @@ def _fetch(self, limit=None):
             self._raiseCursorError(
                 api.FetchFailedError, "fetch() on closed connection or empty query set"
             )
-            return
+            return  # Still return in case a custom errorHandler doesn't raise
 
         if self.rs.State == adc.adStateClosed or self.rs.BOF or self.rs.EOF:
             return list()
diff --git a/adodbapi/apibase.py b/adodbapi/apibase.py
index 87a5317eb8..f1fb298489 100644
--- a/adodbapi/apibase.py
+++ b/adodbapi/apibase.py
@@ -13,15 +13,20 @@
 import sys
 import time
 from collections.abc import Callable, Iterable, Mapping
+from typing import TYPE_CHECKING, NoReturn
 
-# noinspection PyUnresolvedReferences
 from . import ado_consts as adc
 
+if TYPE_CHECKING:
+    from adodbapi.adodbapi import Connection, Cursor
+
 verbose = False  # debugging flag
 
 
 # ------- Error handlers ------
-def standardErrorHandler(connection, cursor, errorclass, errorvalue):
+def standardErrorHandler(
+    connection: Connection, cursor: Cursor, errorclass: type[Error], errorvalue: object
+) -> NoReturn:
     err = (errorclass, errorvalue)
     try:
         connection.messages.append(err)
diff --git a/adodbapi/examples/db_print.py b/adodbapi/examples/db_print.py
index 33a6511388..52a6a5bc75 100644
--- a/adodbapi/examples/db_print.py
+++ b/adodbapi/examples/db_print.py
@@ -50,7 +50,7 @@
         print("")
         print("result data description is:")
         print("            NAME Type         DispSize IntrnlSz Prec Scale Null?")
-        for d in c.description:
+        for d in c.description or ():
             print(
                 ("%16s %-12s %8s %8d %4d %5d %s")
                 % (d[0], adc.adTypeNames[d[1]], d[2], d[3], d[4], d[5], bool(d[6]))
@@ -59,10 +59,10 @@
         print("str() of first five records are...")
 
         # get the results
-        db = c.fetchmany(5)
+        db_result = c.fetchmany(5)
 
         # print them
-        for rec in db:
+        for rec in db_result:
             print(rec)
 
         print("")
diff --git a/com/win32com/client/__init__.py b/com/win32com/client/__init__.py
index b4aae20a8c..3217a97aa0 100644
--- a/com/win32com/client/__init__.py
+++ b/com/win32com/client/__init__.py
@@ -521,6 +521,8 @@ def register_record_class(cls):
 # The base of all makepy generated classes
 ############################################
 class DispatchBaseClass:
+    Properties_: DispatchBaseClass
+
     def __init__(self, oobj=None):
         if oobj is None:
             oobj = pythoncom.new(self.CLSID)
diff --git a/com/win32com/client/combrowse.py b/com/win32com/client/combrowse.py
index 46d0fef2af..585e1166b1 100644
--- a/com/win32com/client/combrowse.py
+++ b/com/win32com/client/combrowse.py
@@ -24,6 +24,7 @@
 """
 
 import sys
+from typing import Any, TypeVar
 
 import pythoncom
 import pywintypes
@@ -33,8 +34,14 @@
 from pywin.tools import browser
 from win32com.client import util
 
+# Representing the full set of HLICOM subclasses generics
+# would also require statically exposing many types from pythoncom.
+# So make the type parameter optional and using `__init__` inference for now,
+# and consider relying on typeshed's `pywin32-stubs` later.
+_HLICOMT = TypeVar("_HLICOMT", default=Any)  # incomplete
 
-class HLIRoot(browser.HLIPythonObject):
+
+class HLIRoot(browser.HLIPythonObject[None]):
     def __init__(self, title):
         super().__init__(name=title)
 
@@ -51,7 +58,7 @@ def __lt__(self, other):
         return self.name < other.name
 
 
-class HLICOM(browser.HLIPythonObject):
+class HLICOM(browser.HLIPythonObject[_HLICOMT]):
     def GetText(self):
         return self.name
 
diff --git a/com/win32com/client/dynamic.py b/com/win32com/client/dynamic.py
index 3738da9031..5306cd6dc3 100644
--- a/com/win32com/client/dynamic.py
+++ b/com/win32com/client/dynamic.py
@@ -16,6 +16,8 @@
 
 """
 
+from __future__ import annotations
+
 import traceback
 from itertools import chain
 from types import MethodType
@@ -185,6 +187,8 @@ def DumbDispatch(
 
 
 class CDispatch:
+    Properties_: CDispatch
+
     def __init__(self, IDispatch, olerepr, userName=None, lazydata=None):
         if userName is None:
             userName = "<unknown>"
diff --git a/pyrightconfig.json b/pyrightconfig.json
index 6bf7f9184f..b2824c83a1 100644
--- a/pyrightconfig.json
+++ b/pyrightconfig.json
@@ -37,7 +37,6 @@
   "reportCallIssue": "warning",
   "reportOperatorIssue": "warning",
   "reportOptionalCall": "warning",
-  "reportOptionalIterable": "warning",
   "reportOptionalMemberAccess": "warning",
   "reportOptionalSubscript": "warning",
   // Too many dynamically generated modules. This will require type stubs to properly fix.
diff --git a/pythonwin/pywin/debugger/debugger.py b/pythonwin/pywin/debugger/debugger.py
index 72b9cf2dc4..803e1a3a0a 100644
--- a/pythonwin/pywin/debugger/debugger.py
+++ b/pythonwin/pywin/debugger/debugger.py
@@ -1,12 +1,13 @@
-# debugger.py
+"""A debugger for Pythonwin.  Built from pdb.
 
-# A debugger for Pythonwin.  Built from pdb.
+Mark Hammond (MHammond@skippinet.com.au) - Dec 94.
 
-# Mark Hammond (MHammond@skippinet.com.au) - Dec 94.
+usage:
+>>> import pywin.debugger
+>>> pywin.debugger.GetDebugger().run("command")
+"""
 
-# usage:
-# >>> import pywin.debugger
-# >>> pywin.debugger.GetDebugger().run("command")
+from __future__ import annotations
 
 import bdb
 import os
@@ -15,6 +16,7 @@
 import sys
 import traceback
 import types
+from typing import TypeVar
 
 import commctrl
 import pywin.docking.DockingBar
@@ -28,6 +30,8 @@
 
 from .dbgcon import *
 
+_T = TypeVar("_T")
+
 LVN_ENDLABELEDIT = commctrl.LVN_ENDLABELEDITW
 
 
@@ -44,11 +48,11 @@ def _LineStateToMarker(ls):
     return MARKER_BREAKPOINT
 
 
-class HierListItem(browser.HLIPythonObject):
+class HierListItem(browser.HLIPythonObject[_T]):
     pass
 
 
-class HierFrameItem(HierListItem):
+class HierFrameItem(HierListItem[types.FrameType]):
     def __init__(self, frame, debugger):
         HierListItem.__init__(self, frame, repr(frame))
         self.debugger = debugger
@@ -89,16 +93,16 @@ def TakeDefaultAction(self):
         return 1
 
 
-class HierFrameDict(browser.HLIDict):
-    def __init__(self, dict, name, bitmapColumn):
+class HierFrameDict(browser.HLIDict[str, _T]):
+    def __init__(self, dict: dict[str, _T], name, bitmapColumn):
         self.bitmapColumn = bitmapColumn
-        browser.HLIDict.__init__(self, dict, name)
+        super().__init__(dict, name)
 
     def GetBitmapColumn(self):
         return self.bitmapColumn
 
 
-class NoStackAvailableItem(HierListItem):
+class NoStackAvailableItem(HierListItem[None]):
     def __init__(self, why):
         HierListItem.__init__(self, None, why)
 
@@ -112,7 +116,7 @@ def GetBitmapColumn(self):
         return 8
 
 
-class HierStackRoot(HierListItem):
+class HierStackRoot(HierListItem["Debugger"]):
     def __init__(self, debugger):
         HierListItem.__init__(self, debugger, None)
         self.last_stack = []
diff --git a/pythonwin/pywin/tools/browser.py b/pythonwin/pywin/tools/browser.py
index b5629dc065..608cfb8938 100644
--- a/pythonwin/pywin/tools/browser.py
+++ b/pythonwin/pywin/tools/browser.py
@@ -1,12 +1,18 @@
-# basic module browser.
+"""
+basic module browser.
+
+usage:
+>>> import browser
+>>> browser.Browse()
+or
+>>> browser.Browse(your_module)
+"""
+
+from __future__ import annotations
 
-# usage:
-# >>> import browser
-# >>> browser.Browse()
-# or
-# >>> browser.Browse(your_module)
 import sys
 import types
+from typing import TYPE_CHECKING, Any, Generic, TypeVar
 
 import __main__
 import win32ui
@@ -14,13 +20,25 @@
 
 from . import hierlist
 
+if TYPE_CHECKING:
+    from _typeshed import SupportsLenAndGetItem
+
+_T = TypeVar("_T")
+_KT = TypeVar("_KT")
+_VT = TypeVar("_VT")
+_SequenceT = TypeVar("_SequenceT", bound="SupportsLenAndGetItem[Any]")
+
 special_names = ["__doc__", "__name__", "__self__"]
 
 
 #
 # HierList items
-class HLIPythonObject(hierlist.HierListItem):
-    def __init__(self, myobject=None, name=None):
+class HLIPythonObject(hierlist.HierListItem, Generic[_T]):
+    def __init__(
+        self,
+        myobject: _T = None,  # type: ignore[assignment] # False-positive, None is part of the bound type
+        name=None,
+    ):
         hierlist.HierListItem.__init__(self)
         self.myobject = myobject
         self.knownExpandable = None
@@ -129,7 +147,7 @@ def TakeDefaultAction(self):
         ShowObject(self.myobject, self.name)
 
 
-class HLIDocString(HLIPythonObject):
+class HLIDocString(HLIPythonObject[str]):
     def GetHLIType(self):
         return "DocString"
 
@@ -143,22 +161,22 @@ def GetBitmapColumn(self):
         return 6
 
 
-class HLIModule(HLIPythonObject):
+class HLIModule(HLIPythonObject[types.ModuleType]):
     def GetHLIType(self):
         return "Module"
 
 
-class HLIFrame(HLIPythonObject):
+class HLIFrame(HLIPythonObject[types.FrameType]):
     def GetHLIType(self):
         return "Stack Frame"
 
 
-class HLITraceback(HLIPythonObject):
+class HLITraceback(HLIPythonObject[types.TracebackType]):
     def GetHLIType(self):
         return "Traceback"
 
 
-class HLIClass(HLIPythonObject):
+class HLIClass(HLIPythonObject[type]):
     def GetHLIType(self):
         return "Class"
 
@@ -170,7 +188,7 @@ def GetSubList(self):
         return ret
 
 
-class HLIMethod(HLIPythonObject):
+class HLIMethod(HLIPythonObject[str]):
     # myobject is just a string for methods.
     def GetHLIType(self):
         return "Method"
@@ -179,7 +197,7 @@ def GetText(self):
         return "Method: " + self.myobject + "()"
 
 
-class HLICode(HLIPythonObject):
+class HLICode(HLIPythonObject[types.CodeType]):
     def GetHLIType(self):
         return "Code"
 
@@ -197,7 +215,7 @@ def GetSubList(self):
         return ret
 
 
-class HLIInstance(HLIPythonObject):
+class HLIInstance(HLIPythonObject[_T]):
     def GetHLIType(self):
         return "Instance"
 
@@ -219,12 +237,12 @@ def GetSubList(self):
         return ret
 
 
-class HLIBuiltinFunction(HLIPythonObject):
+class HLIBuiltinFunction(HLIPythonObject[types.BuiltinFunctionType]):
     def GetHLIType(self):
         return "Builtin Function"
 
 
-class HLIFunction(HLIPythonObject):
+class HLIFunction(HLIPythonObject[types.FunctionType]):
     def GetHLIType(self):
         return "Function"
 
@@ -240,7 +258,7 @@ def GetSubList(self):
         return ret
 
 
-class HLISeq(HLIPythonObject):
+class HLISeq(HLIPythonObject[_SequenceT]):
     def GetHLIType(self):
         return "Sequence (abstract!)"
 
@@ -257,17 +275,17 @@ def GetSubList(self):
         return ret
 
 
-class HLIList(HLISeq):
+class HLIList(HLISeq[list[_T]]):
     def GetHLIType(self):
         return "List"
 
 
-class HLITuple(HLISeq):
+class HLITuple(HLISeq[tuple[_T]]):
     def GetHLIType(self):
         return "Tuple"
 
 
-class HLIDict(HLIPythonObject):
+class HLIDict(HLIPythonObject[dict[_KT, _VT]]):
     def GetHLIType(self):
         return "Dict"
 
@@ -285,7 +303,7 @@ def GetSubList(self):
 
 
 # strings and Unicode have builtin methods, but we don't really want to see these
-class HLIString(HLIPythonObject):
+class HLIString(HLIPythonObject[str]):
     def IsExpandable(self):
         return 0
 
diff --git a/uv.lock b/uv.lock
new file mode 100644
index 0000000000..a1ce2cec70
--- /dev/null
+++ b/uv.lock
@@ -0,0 +1,270 @@
+version = 1
+revision = 3
+requires-python = ">=3.14"
+
+[manifest]
+
+[manifest.dependency-groups]
+checkers = [
+    { name = "clang-format", specifier = "==18.1.8" },
+    { name = "ruff", specifier = "==0.14.14" },
+]
+dev = [
+    { name = "clang-format", specifier = "==18.1.8" },
+    { name = "mypy", marker = "python_full_version >= '3.9'", specifier = "==1.16.*" },
+    { name = "pre-commit" },
+    { name = "pyopengl" },
+    { name = "pyright", specifier = "==1.1.401" },
+    { name = "ruff", specifier = "==0.14.14" },
+    { name = "types-setuptools" },
+]
+type-checkers = [
+    { name = "mypy", marker = "python_full_version >= '3.9'", specifier = "==1.16.*" },
+    { name = "pyopengl" },
+    { name = "pyright", specifier = "==1.1.401" },
+    { name = "types-setuptools" },
+]
+
+[[package]]
+name = "cfgv"
+version = "3.5.0"
+source = { registry = "https://pypi.org/simple" }
+sdist = { url = "https://files.pythonhosted.org/packages/4e/b5/721b8799b04bf9afe054a3899c6cf4e880fcf8563cc71c15610242490a0c/cfgv-3.5.0.tar.gz", hash = "sha256:d5b1034354820651caa73ede66a6294d6e95c1b00acc5e9b098e917404669132", size = 7334, upload-time = "2025-11-19T20:55:51.612Z" }
+wheels = [
+    { url = "https://files.pythonhosted.org/packages/db/3c/33bac158f8ab7f89b2e59426d5fe2e4f63f7ed25df84c036890172b412b5/cfgv-3.5.0-py2.py3-none-any.whl", hash = "sha256:a8dc6b26ad22ff227d2634a65cb388215ce6cc96bbcc5cfde7641ae87e8dacc0", size = 7445, upload-time = "2025-11-19T20:55:50.744Z" },
+]
+
+[[package]]
+name = "clang-format"
+version = "18.1.8"
+source = { registry = "https://pypi.org/simple" }
+sdist = { url = "https://files.pythonhosted.org/packages/94/ef/e8d7160175753f11c939a842fa2b4fcd1221136b7232b0570e890ff1d96d/clang_format-18.1.8.tar.gz", hash = "sha256:065ddb7fdd0cb329976115fa03500dd560d9753dd50c25a269776648e6e6bf35", size = 11078, upload-time = "2024-06-28T10:18:22.183Z" }
+wheels = [
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