diff --git a/devDocs/unreachableObjects.md b/devDocs/unreachableObjects.md
new file mode 100644
index 00000000000..0dcb0fb1d5a
--- /dev/null
+++ b/devDocs/unreachableObjects.md
@@ -0,0 +1,66 @@
+# Garbage collection errors
+NVDA's `garbageHandler.py` monitors Python's cyclic garbage collector and reports
+on objects that are unreachable.
+Cyclic references are typically a symptom of bad design, and can cause major problems for certain objects.
+For instance, cyclic references involving COM objects may cause a deadlock if the garbage collector happens to break the cycle and release the COM object in the wrong thread.
+
+## How to know about a cyclic reference?
+The log may contain errors like the following.
+```
+WARNING - garbageHandler.notifyObjectDeletion (10:45:23.171) - MainThread (21820):
+Garbage collector has found one or more unreachable objects. See further warnings for specific objects.
+...
+WARNING - garbageHandler.notifyObjectDeletion (10:45:23.171) - MainThread (21820):
+Deleting unreachable object <eventHandler._EventExecuter object at 0x1AC15350>
+ERROR - garbageHandler._collectionCallback (10:45:23.172) - MainThread (21820):
+Found at least 1 unreachable objects in run
+```
+
+## How to debug a cyclic reference?
+
+Once you can reliably reproduce the log error, you can tell the garbage collector to save all unreachable objects.
+After an unreachable object is detected the references to the unreachable object can be inspected via the python console.
+Inspecting this should give you a fair idea of where the issue is occurring.
+
+1. Open the NVDA Python console `NVDA+control+z`
+1. Enable saving all objects:
+   ``` python
+   import gc
+   gc.set_debug(gc.DEBUG_SAVEALL)
+   ```
+1. Reproduce the unreachable object error.
+1. If garbage collection errors have not yet been logged, force a collect by calling:
+   ``` python
+   gc.collect()
+   ```
+
+1. All unreachable objects will now be stored in `gc.garbage`.
+   It may be a very large list.
+   Some tricks for narrowing this list down:
+   - From the log, you can get the memory address (`id`) of the object.
+     Then use:
+     ``` python
+     memoryAddress = 0xabcd123
+     obj = None
+     for o in gc.garbage:
+     	if memoryAddress == id(o)
+     		obj = o
+     ```
+   - Listing the types collected, look for the type(s) matching the log message:
+     ``` python
+     for index, o in enumerate(gc.garbage):
+     	print(index, type(o))
+     ```
+1. Once you have a reference (`obj`) to the unreachable object, see what other objects refer to an object you can call.
+   You can do this by using `gc.get_referrers`.
+   The python console has a reference to `obj`, there may be a lot of output.
+   You can reduce this by looking at the types and following the most relevant.
+   ``` python
+   for index, o in enumerate(gc.get_referrers(obj)):
+   	print(index, type(o))
+   ```
+1. Continue following the references to build a picture of the cycle.
+
+## Typical problems
+Some examples of common issues:
+- Exceptions caught and assigned to a local variable.
diff --git a/source/core.py b/source/core.py
index 630284f4483..b2c1e7584f6 100644
--- a/source/core.py
+++ b/source/core.py
@@ -14,10 +14,6 @@ class CallCancelled(Exception):
 	"""Raised when a call is cancelled.
 	"""
 
-# Apply several monkey patches to comtypes
-# noinspection PyUnresolvedReferences
-import comtypesMonkeyPatches
-
 # Initialise comtypes.client.gen_dir and the comtypes.gen search path 
 # and Append our comInterfaces directory to the comtypes.gen search path.
 import comtypes
diff --git a/source/gui/__init__.py b/source/gui/__init__.py
index f0305d3db54..2be10911381 100644
--- a/source/gui/__init__.py
+++ b/source/gui/__init__.py
@@ -560,21 +560,8 @@ def initialize():
 		# otherwise the system default will be used
 		mainFrame.SetLayoutDirection(wxLang.LayoutDirection)
 	wx.GetApp().SetTopWindow(mainFrame)
-	# In wxPython >= 4.1,
-	# wx.CallAfter no longer executes callbacks while NVDA's main thread is within apopup menu or message box.
-	# To work around this,
-	# Monkeypatch wx.CallAfter to
-	# post a WM_NULL message to our top-level window after calling the original CallAfter,
-	# which causes wx's event loop to wake up enough to execute the callback.
-	old_wx_CallAfter = wx.CallAfter
-
-	def wx_CallAfter_wrapper(func, *args, **kwargs):
-		old_wx_CallAfter(func, *args, **kwargs)
-		# mainFrame may be None as NVDA could be terminating.
-		topHandle = mainFrame.Handle if mainFrame else None
-		if topHandle:
-			winUser.PostMessage(topHandle, winUser.WM_NULL, 0, 0)
-	wx.CallAfter = wx_CallAfter_wrapper
+	import monkeyPatches
+	monkeyPatches.applyWxMonkeyPatches(mainFrame, winUser, wx)
 
 
 def terminate():
diff --git a/source/monkeyPatches/__init__.py b/source/monkeyPatches/__init__.py
new file mode 100644
index 00000000000..b970d836b73
--- /dev/null
+++ b/source/monkeyPatches/__init__.py
@@ -0,0 +1,19 @@
+# A part of NonVisual Desktop Access (NVDA)
+# Copyright (C) 2021 NV Access Limited
+# This file is covered by the GNU General Public License.
+# See the file COPYING for more details.
+
+from . import wxMonkeyPatches
+
+
+applyWxMonkeyPatches = wxMonkeyPatches.apply
+
+
+def applyMonkeyPatches():
+	# Apply several monkey patches to comtypes
+	# F401 - imported but unused: Patches are applied during import
+	from . import comtypesMonkeyPatches  # noqa: F401
+
+	# Apply patches to Enum, prevent cyclic references on ValueError during construction
+	from . import enumPatches
+	enumPatches.replace__new__()
diff --git a/source/comtypesMonkeyPatches.py b/source/monkeyPatches/comtypesMonkeyPatches.py
similarity index 100%
rename from source/comtypesMonkeyPatches.py
rename to source/monkeyPatches/comtypesMonkeyPatches.py
diff --git a/source/monkeyPatches/enumPatches.py b/source/monkeyPatches/enumPatches.py
new file mode 100644
index 00000000000..6abee38b6c7
--- /dev/null
+++ b/source/monkeyPatches/enumPatches.py
@@ -0,0 +1,60 @@
+# A part of NonVisual Desktop Access (NVDA)
+# Copyright (C) 2021 NV Access Limited
+# This file is covered by the GNU General Public License.
+# See the file COPYING for more details.
+
+
+def replace__new__():
+	import enum
+	# prevent cyclic references on ValueError during construction
+	enum.Enum.__new__ = _replacement__new__
+
+
+def _replacement__new__(cls, value):
+	""" Copied from python standard library enum.py class Enum.
+	Prevent cyclic references on ValueError during construction.
+	Local variable exc must be deleted, otherwise:
+	- ref to exc held by the frame
+	- ref to traceback held by exc
+	- ref to frame held by traceback
+	"""
+	# all enum instances are actually created during class construction
+	# without calling this method; this method is called by the metaclass'
+	# __call__ (i.e. Color(3) ), and by pickle
+	if type(value) is cls:
+		# For lookups like Color(Color.RED)
+		return value
+	# by-value search for a matching enum member
+	# see if it's in the reverse mapping (for hashable values)
+	try:
+		return cls._value2member_map_[value]
+	except KeyError:
+		# Not found, no need to do long O(n) search
+		pass
+	except TypeError:
+		# not there, now do long search -- O(n) behavior
+		for member in cls._member_map_.values():
+			if member._value_ == value:
+				return member
+	# still not found -- try _missing_ hook
+	try:
+		result = cls._missing_(value)
+	except Exception as e:
+		e.__context__ = ValueError("%r is not a valid %s" % (value, cls.__name__))
+		raise e
+
+	if isinstance(result, cls):
+		return result
+
+	with ValueError(
+		"%r is not a valid %s" % (value, cls.__name__)
+	) as ve_exc:
+		if result is None:
+			raise ve_exc
+
+		te_exc = TypeError(
+			'error in %s._missing_: returned %r instead of None or a valid member'
+			% (cls.__name__, result)
+		)
+		te_exc.__context__ = ve_exc
+		raise te_exc
diff --git a/source/monkeyPatches/wxMonkeyPatches.py b/source/monkeyPatches/wxMonkeyPatches.py
new file mode 100644
index 00000000000..691edf9e41f
--- /dev/null
+++ b/source/monkeyPatches/wxMonkeyPatches.py
@@ -0,0 +1,23 @@
+# A part of NonVisual Desktop Access (NVDA)
+# Copyright (C) 2021 NV Access Limited
+# This file is covered by the GNU General Public License.
+# See the file COPYING for more details.
+
+
+def apply(mainFrame, winUser, wx):
+	# In wxPython >= 4.1,
+	# wx.CallAfter no longer executes callbacks while NVDA's main thread is within a popup menu or message box.
+	# To work around this,
+	# MonkeyPatch wx.CallAfter to
+	# post a WM_NULL message to our top-level window after calling the original CallAfter,
+	# which causes wx's event loop to wake up enough to execute the callback.
+	old_wx_CallAfter = wx.CallAfter
+
+	def wx_CallAfter_wrapper(func, *args, **kwargs):
+		old_wx_CallAfter(func, *args, **kwargs)
+		# mainFrame may be None as NVDA could be terminating.
+		topHandle = mainFrame.Handle if mainFrame else None
+		if topHandle:
+			winUser.PostMessage(topHandle, winUser.WM_NULL, 0, 0)
+
+	wx.CallAfter = wx_CallAfter_wrapper
diff --git a/source/nvda.pyw b/source/nvda.pyw
index 2a170591d61..455e1b91fea 100755
--- a/source/nvda.pyw
+++ b/source/nvda.pyw
@@ -17,6 +17,9 @@ import typing
 import globalVars
 import ctypes
 from ctypes import wintypes
+import monkeyPatches
+
+monkeyPatches.applyMonkeyPatches()
 
 #: logger to use before the true NVDA log is initialised.
 # Ideally, all logging would be captured by the NVDA log, however this would introduce contention