diff --git a/src/Avalonia.Controls/Primitives/PopupRoot.cs b/src/Avalonia.Controls/Primitives/PopupRoot.cs
index 2f6df862cf..99ef93d8e8 100644
--- a/src/Avalonia.Controls/Primitives/PopupRoot.cs
+++ b/src/Avalonia.Controls/Primitives/PopupRoot.cs
@@ -17,7 +17,6 @@ namespace Avalonia.Controls.Primitives
     /// </summary>
     public sealed class PopupRoot : WindowBase, IInteractive, IHostedVisualTreeRoot, IDisposable, IStyleHost, IPopupHost
     {
-        private readonly TopLevel _parent;
         private PopupPositionerParameters _positionerParameters;        
 
         /// <summary>
@@ -47,7 +46,7 @@ namespace Avalonia.Controls.Primitives
         public PopupRoot(TopLevel parent, IPopupImpl impl, IAvaloniaDependencyResolver? dependencyResolver)
             : base(impl, dependencyResolver)
         {
-            _parent = parent;
+            ParentTopLevel = parent;
         }
 
         /// <summary>
@@ -73,6 +72,8 @@ namespace Avalonia.Controls.Primitives
         /// </summary>
         IStyleHost? IStyleHost.StylingParent => Parent;
 
+        public TopLevel ParentTopLevel { get; }
+
         /// <inheritdoc/>
         public void Dispose()
         {
@@ -91,7 +92,7 @@ namespace Avalonia.Controls.Primitives
             PopupPositionerConstraintAdjustment constraintAdjustment = PopupPositionerConstraintAdjustment.All,
             Rect? rect = null)
         {
-            _positionerParameters.ConfigurePosition(_parent, target,
+            _positionerParameters.ConfigurePosition(ParentTopLevel, target,
                 placement, offset, anchor, gravity, constraintAdjustment, rect);
 
             if (_positionerParameters.Size != default)
diff --git a/src/Avalonia.Diagnostics/Diagnostics/Views/MainWindow.xaml.cs b/src/Avalonia.Diagnostics/Diagnostics/Views/MainWindow.xaml.cs
index 7abe2570e3..3b143d3b58 100644
--- a/src/Avalonia.Diagnostics/Diagnostics/Views/MainWindow.xaml.cs
+++ b/src/Avalonia.Diagnostics/Diagnostics/Views/MainWindow.xaml.cs
@@ -162,13 +162,18 @@ namespace Avalonia.Diagnostics.Views
                 return;
             }
 
-            var root = Root as TopLevel
-                ?? vm.PointerOverRoot as TopLevel;
+            var root = vm.PointerOverRoot as TopLevel;
+
             if (root is null)
             {
                 return;
             }
 
+            if (root is PopupRoot pr && pr.ParentTopLevel != null)
+            {
+                root = pr.ParentTopLevel;
+            }
+
             switch (e.Modifiers)
             {
                 case RawInputModifiers.Control when (e.Key == Key.LeftShift || e.Key == Key.RightShift):