diff --git a/src/modules/keyboardmanager/common/Helpers.cpp b/src/modules/keyboardmanager/common/Helpers.cpp
index ffbffacc70..ec188d758c 100644
--- a/src/modules/keyboardmanager/common/Helpers.cpp
+++ b/src/modules/keyboardmanager/common/Helpers.cpp
@@ -26,3 +26,19 @@ IInspectable getSiblingElement(IInspectable const& element)
     parentElement.Children().IndexOf(frameworkElement, index);
     return parentElement.Children().GetAt(index + 1);
 }
+
+// Function to return if the key is an extended key which requires the use of the extended key flag
+bool isExtendedKey(DWORD key)
+{
+    switch (key)
+    {
+    case VK_RCONTROL:
+    case VK_RMENU:
+    case VK_NUMLOCK:
+    case VK_SNAPSHOT:
+    case VK_CANCEL:
+        return true;
+    default:
+        return false;
+    }
+}
diff --git a/src/modules/keyboardmanager/common/Helpers.h b/src/modules/keyboardmanager/common/Helpers.h
index 9371ecd8e5..7a2d3bc8e2 100644
--- a/src/modules/keyboardmanager/common/Helpers.h
+++ b/src/modules/keyboardmanager/common/Helpers.h
@@ -32,3 +32,6 @@ std::vector<T> convertWStringVectorToIntegerVector(const std::vector<std::wstrin
 
     return typeVector;
 }
+
+// Function to return if the key is an extended key which requires the use of the extended key flag
+bool isExtendedKey(DWORD key);
diff --git a/src/modules/keyboardmanager/common/Shortcut.cpp b/src/modules/keyboardmanager/common/Shortcut.cpp
index b35c3bf984..1432175cd7 100644
--- a/src/modules/keyboardmanager/common/Shortcut.cpp
+++ b/src/modules/keyboardmanager/common/Shortcut.cpp
@@ -539,8 +539,8 @@ bool Shortcut::CheckModifiersKeyboardState() const
 // Function to check if any keys are pressed down except those in the shortcut
 bool Shortcut::IsKeyboardStateClearExceptShortcut() const
 {
-    // Iterate through all the virtual key codes
-    for (int keyVal = 0; keyVal < 0x100; keyVal++)
+    // Iterate through all the virtual key codes - 0xFF is set to key down because of the Num Lock
+    for (int keyVal = 0; keyVal < 0xFF; keyVal++)
     {
         // Skip mouse buttons. Keeping this could cause a remapping to fail if a mouse button is also pressed at the same time
         if (keyVal == VK_LBUTTON || keyVal == VK_RBUTTON || keyVal == VK_MBUTTON || keyVal == VK_XBUTTON1 || keyVal == VK_XBUTTON2)
diff --git a/src/modules/keyboardmanager/dll/dllmain.cpp b/src/modules/keyboardmanager/dll/dllmain.cpp
index 895f459a49..eb436d09ed 100644
--- a/src/modules/keyboardmanager/dll/dllmain.cpp
+++ b/src/modules/keyboardmanager/dll/dllmain.cpp
@@ -152,7 +152,7 @@ public:
                 PowerToysSettings::CustomActionObject::from_json_string(action);
             HINSTANCE hInstance = reinterpret_cast<HINSTANCE>(&__ImageBase);
 
-            if (action_object.get_name() == L"RemapKeyboard") 
+            if (action_object.get_name() == L"RemapKeyboard")
             {
                 if (!CheckEditKeyboardWindowActive())
                 {
@@ -325,6 +325,10 @@ public:
         keyEventArray[index].type = inputType;
         keyEventArray[index].ki.wVk = keyCode;
         keyEventArray[index].ki.dwFlags = flags;
+        if (isExtendedKey(keyCode))
+        {
+            keyEventArray[index].ki.dwFlags |= KEYEVENTF_EXTENDEDKEY;
+        }
         keyEventArray[index].ki.dwExtraInfo = extraInfo;
     }