diff --git a/src/modules/fancyzones/FancyZonesLib/WindowMoveHandler.cpp b/src/modules/fancyzones/FancyZonesLib/WindowMoveHandler.cpp
index f97baf20ec..4f73ec44cf 100644
--- a/src/modules/fancyzones/FancyZonesLib/WindowMoveHandler.cpp
+++ b/src/modules/fancyzones/FancyZonesLib/WindowMoveHandler.cpp
@@ -53,7 +53,8 @@ namespace WindowMoveHandlerUtils
 WindowMoveHandler::WindowMoveHandler(const std::function<void()>& keyUpdateCallback) :
     m_mouseState(false),
     m_mouseHook(std::bind(&WindowMoveHandler::OnMouseDown, this)),
-    m_shiftKeyState(keyUpdateCallback),
+    m_leftShiftKeyState(keyUpdateCallback),
+    m_rightShiftKeyState(keyUpdateCallback),
     m_ctrlKeyState(keyUpdateCallback),
     m_keyUpdateCallback(keyUpdateCallback)
 {
@@ -88,7 +89,8 @@ void WindowMoveHandler::MoveSizeStart(HWND window, HMONITOR monitor, POINT const
         m_mouseHook.enable();
     }
 
-    m_shiftKeyState.enable();
+    m_leftShiftKeyState.enable();
+    m_rightShiftKeyState.enable();
     m_ctrlKeyState.enable();
 
     // This updates m_dragEnabled depending on if the shift key is being held down
@@ -214,8 +216,12 @@ void WindowMoveHandler::MoveSizeEnd(HWND window, const std::unordered_map<HMONIT
         return;
     }
 
+    bool leftShiftPressed = m_leftShiftKeyState.state();
+    bool rightShiftPressed = m_rightShiftKeyState.state();
+
     m_mouseHook.disable();
-    m_shiftKeyState.disable();
+    m_leftShiftKeyState.disable();
+    m_rightShiftKeyState.disable();
     m_ctrlKeyState.disable();
 
     if (m_draggedWindowWorkArea)
@@ -235,6 +241,19 @@ void WindowMoveHandler::MoveSizeEnd(HWND window, const std::unordered_map<HMONIT
         }
         else
         {
+            if (FancyZonesSettings::settings().shiftDrag)
+            {
+                if (leftShiftPressed)
+                {
+                    SwallowKey(VK_LSHIFT);
+                }
+
+                if (rightShiftPressed)
+                {
+                    SwallowKey(VK_RSHIFT);
+                }
+            }
+
             workArea->MoveSizeEnd(m_draggedWindow);
         }
     }
@@ -360,11 +379,11 @@ void WindowMoveHandler::UpdateDragState() noexcept
 {
     if (FancyZonesSettings::settings().shiftDrag)
     {
-        m_dragEnabled = (m_shiftKeyState.state() ^ m_mouseState);
+        m_dragEnabled = ((m_leftShiftKeyState.state() || m_rightShiftKeyState.state()) ^ m_mouseState);
     }
     else
     {
-        m_dragEnabled = !(m_shiftKeyState.state() ^ m_mouseState);
+        m_dragEnabled = !((m_leftShiftKeyState.state() || m_rightShiftKeyState.state()) ^ m_mouseState);
     }
 }
 
@@ -410,3 +429,12 @@ void WindowMoveHandler::ResetWindowTransparency() noexcept
         m_windowTransparencyProperties.draggedWindow = nullptr;
     }
 }
+
+void WindowMoveHandler::SwallowKey(const WORD key) noexcept
+{
+    INPUT inputKey[1] = {};
+    inputKey[0].type = INPUT_KEYBOARD;
+    inputKey[0].ki.wVk = key;
+    inputKey[0].ki.dwFlags = KEYEVENTF_KEYUP;
+    SendInput(1, inputKey, sizeof(INPUT));
+}
diff --git a/src/modules/fancyzones/FancyZonesLib/WindowMoveHandler.h b/src/modules/fancyzones/FancyZonesLib/WindowMoveHandler.h
index 1e3c2a1baa..29a8f0488e 100644
--- a/src/modules/fancyzones/FancyZonesLib/WindowMoveHandler.h
+++ b/src/modules/fancyzones/FancyZonesLib/WindowMoveHandler.h
@@ -65,6 +65,7 @@ private:
 
     void SetWindowTransparency(HWND window) noexcept;
     void ResetWindowTransparency() noexcept;
+    void SwallowKey(const WORD key) noexcept;
 
     bool m_inDragging{}; // Whether or not a move/size operation is currently active
     HWND m_draggedWindow{}; // The window that is being moved/sized
@@ -76,7 +77,8 @@ private:
 
     std::atomic<bool> m_mouseState;
     SecondaryMouseButtonsHook m_mouseHook;
-    KeyState<VK_LSHIFT, VK_RSHIFT> m_shiftKeyState;
+    KeyState<VK_LSHIFT> m_leftShiftKeyState;
+    KeyState<VK_RSHIFT> m_rightShiftKeyState;
     KeyState<VK_LCONTROL, VK_RCONTROL> m_ctrlKeyState;
     std::function<void()> m_keyUpdateCallback;
 };