diff --git a/native/Avalonia.Native/src/OSX/AvnWindow.mm b/native/Avalonia.Native/src/OSX/AvnWindow.mm
index 2dee90bfa3..0bd4b0f462 100644
--- a/native/Avalonia.Native/src/OSX/AvnWindow.mm
+++ b/native/Avalonia.Native/src/OSX/AvnWindow.mm
@@ -435,9 +435,23 @@
                 return;
             }
 
-            if(window->WindowState() == Maximized)
+            // If the window has been moved into a position where it's "zoomed"
+            // Then it should be set as Maximized.
+            if (window->WindowState() != Maximized && window->IsZoomed())
             {
-                window->SetWindowState(Normal);
+                window->SetWindowState(Maximized, false);
+            }
+            // We should only return the window state to normal if
+            // the internal window state is maximized, and macOS says
+            // the window is no longer zoomed (I.E, the user has moved it)
+            // Stage Manager will "move" the window when repositioning it
+            // So if the window was "maximized" before, it should stay maximized
+            else if(window->WindowState() == Maximized && !window->IsZoomed())
+            {
+                // If we're moving the window while maximized,
+                // we need to let macOS handle if it should be resized
+                // And not handle it ourselves.
+                window->SetWindowState(Normal, false);
             }
         }
 
diff --git a/native/Avalonia.Native/src/OSX/WindowImpl.h b/native/Avalonia.Native/src/OSX/WindowImpl.h
index fce7273f30..37699082ed 100644
--- a/native/Avalonia.Native/src/OSX/WindowImpl.h
+++ b/native/Avalonia.Native/src/OSX/WindowImpl.h
@@ -71,6 +71,8 @@ BEGIN_INTERFACE_MAP()
     void ExitFullScreenMode ();
 
     virtual HRESULT SetWindowState (AvnWindowState state) override;
+    
+    virtual HRESULT SetWindowState (AvnWindowState state, bool shouldResize);
 
     virtual bool IsModal() override;
     
diff --git a/native/Avalonia.Native/src/OSX/WindowImpl.mm b/native/Avalonia.Native/src/OSX/WindowImpl.mm
index 03f3319bcd..341085ec08 100644
--- a/native/Avalonia.Native/src/OSX/WindowImpl.mm
+++ b/native/Avalonia.Native/src/OSX/WindowImpl.mm
@@ -451,6 +451,10 @@ void WindowImpl::ExitFullScreenMode() {
 }
 
 HRESULT WindowImpl::SetWindowState(AvnWindowState state) {
+    return SetWindowState(state, true);
+}
+
+HRESULT WindowImpl::SetWindowState(AvnWindowState state, bool shouldResize) {
     START_COM_CALL;
 
     @autoreleasepool {
@@ -474,61 +478,63 @@ HRESULT WindowImpl::SetWindowState(AvnWindowState state) {
         if (_shown) {
             _actualWindowState = _lastWindowState;
 
-            switch (state) {
-                case Maximized:
-                    if (currentState == FullScreen) {
-                        ExitFullScreenMode();
-                    }
+            if (shouldResize) {
+                switch (state) {
+                    case Maximized:
+                        if (currentState == FullScreen) {
+                            ExitFullScreenMode();
+                        }
 
-                    lastPositionSet.X = 0;
-                    lastPositionSet.Y = 0;
+                        lastPositionSet.X = 0;
+                        lastPositionSet.Y = 0;
 
-                    if ([Window isMiniaturized]) {
-                        [Window deminiaturize:Window];
-                    }
+                        if ([Window isMiniaturized]) {
+                            [Window deminiaturize:Window];
+                        }
 
-                    if (!IsZoomed()) {
-                        DoZoom();
-                    }
-                    break;
+                        if (!IsZoomed()) {
+                            DoZoom();
+                        }
+                        break;
 
-                case Minimized:
-                    if (currentState == FullScreen) {
-                        ExitFullScreenMode();
-                    } else {
-                        [Window miniaturize:Window];
-                    }
-                    break;
+                    case Minimized:
+                        if (currentState == FullScreen) {
+                            ExitFullScreenMode();
+                        } else {
+                            [Window miniaturize:Window];
+                        }
+                        break;
 
-                case FullScreen:
-                    if ([Window isMiniaturized]) {
-                        [Window deminiaturize:Window];
-                    }
+                    case FullScreen:
+                        if ([Window isMiniaturized]) {
+                            [Window deminiaturize:Window];
+                        }
 
-                    EnterFullScreenMode();
-                    break;
+                        EnterFullScreenMode();
+                        break;
 
-                case Normal:
-                    if ([Window isMiniaturized]) {
-                        [Window deminiaturize:Window];
-                    }
+                    case Normal:
+                        if ([Window isMiniaturized]) {
+                            [Window deminiaturize:Window];
+                        }
 
-                    if (currentState == FullScreen) {
-                        ExitFullScreenMode();
-                    }
+                        if (currentState == FullScreen) {
+                            ExitFullScreenMode();
+                        }
 
-                    if (IsZoomed()) {
-                        if (_decorations == SystemDecorationsFull) {
-                            DoZoom();
-                        } else {
-                            [Window setFrame:_preZoomSize display:true];
-                            auto newFrame = [Window contentRectForFrameRect:[Window frame]].size;
+                        if (IsZoomed()) {
+                            if (_decorations == SystemDecorationsFull) {
+                                DoZoom();
+                            } else {
+                                [Window setFrame:_preZoomSize display:true];
+                                auto newFrame = [Window contentRectForFrameRect:[Window frame]].size;
 
-                            [View setFrameSize:newFrame];
-                        }
+                                [View setFrameSize:newFrame];
+                            }
 
-                    }
-                    break;
+                        }
+                        break;
+                }
             }
 
             WindowEvents->WindowStateChanged(_actualWindowState);