diff --git a/src/Avalonia.Controls/Flyouts/FlyoutBase.cs b/src/Avalonia.Controls/Flyouts/FlyoutBase.cs
index dfbd3f9a366..4801fa69f00 100644
--- a/src/Avalonia.Controls/Flyouts/FlyoutBase.cs
+++ b/src/Avalonia.Controls/Flyouts/FlyoutBase.cs
@@ -219,7 +219,7 @@ protected virtual bool ShowAtCore(Control placementTarget, bool showAtPointer =
                 ((ISetLogicalParent)Popup).SetParent(null);
             }
 
-            if (Popup.PlacementTarget != placementTarget)
+            if (Popup.Parent == null || Popup.PlacementTarget != placementTarget)
             {
                 Popup.PlacementTarget = Target = placementTarget;
                 ((ISetLogicalParent)Popup).SetParent(placementTarget);
diff --git a/tests/Avalonia.Controls.UnitTests/FlyoutTests.cs b/tests/Avalonia.Controls.UnitTests/FlyoutTests.cs
index 8b77074960d..776b4508c20 100644
--- a/tests/Avalonia.Controls.UnitTests/FlyoutTests.cs
+++ b/tests/Avalonia.Controls.UnitTests/FlyoutTests.cs
@@ -451,6 +451,28 @@ public void Should_Reset_Popup_Parent_On_Target_Detached()
                 Assert.Null(popup.Parent);
             }
         }
+        
+        [Fact]
+        public void Should_Reset_Popup_Parent_On_Target_Attach_Following_Detach()
+        {
+            using (CreateServicesWithFocus())
+            {
+                var userControl = new UserControl();
+                var window = PreparedWindow(userControl);
+                window.Show();
+                
+                var flyout = new TestFlyout();
+                flyout.ShowAt(userControl);
+                
+                var popup = Assert.IsType<Popup>(flyout.Popup);
+                Assert.NotNull(popup.Parent);
+                
+                flyout.Hide();
+                
+                flyout.ShowAt(userControl);
+                Assert.NotNull(popup.Parent);
+            }
+        }
 
         [Fact]
         public void ContextFlyout_Can_Be_Set_In_Styles()