diff --git a/modules/javafx.controls/src/main/java/javafx/scene/control/ContextMenu.java b/modules/javafx.controls/src/main/java/javafx/scene/control/ContextMenu.java
index 1c90448cc72..db9b29b066b 100644
--- a/modules/javafx.controls/src/main/java/javafx/scene/control/ContextMenu.java
+++ b/modules/javafx.controls/src/main/java/javafx/scene/control/ContextMenu.java
@@ -25,6 +25,8 @@
 
 package javafx.scene.control;
 
+import javafx.geometry.Bounds;
+import javafx.geometry.NodeOrientation;
 import javafx.beans.property.ObjectProperty;
 import javafx.beans.property.ObjectPropertyBase;
 import javafx.collections.ListChangeListener.Change;
@@ -44,6 +46,7 @@
 import com.sun.javafx.collections.TrackableObservableList;
 import com.sun.javafx.tk.Toolkit;
 import com.sun.javafx.util.Utils;
+import com.sun.javafx.stage.PopupWindowHelper;
 
 /**
  * <p>
@@ -249,10 +252,10 @@ public void show(Node anchor, Side side, double dx, double dy) {
         if (anchor == null) return;
         if (getItems().size() == 0) return;
 
+        PopupWindowHelper.ownerWindow(this).set(anchor.getScene().getWindow());
+        PopupWindowHelper.ownerNode(this).set(anchor);
+        PopupWindowHelper.applyStylesheetFromOwner(this, anchor.getScene().getWindow());
         getScene().setNodeOrientation(anchor.getEffectiveNodeOrientation());
-        if (getScene().getStylesheets().isEmpty()) {
-            getScene().getStylesheets().setAll(anchor.getScene().getStylesheets());
-        }
 
         HPos hpos = side == Side.LEFT ? HPos.LEFT : side == Side.RIGHT ? HPos.RIGHT : HPos.CENTER;
         VPos vpos = side == Side.TOP ? VPos.TOP : side == Side.BOTTOM ? VPos.BOTTOM : VPos.CENTER;
diff --git a/modules/javafx.controls/src/test/java/test/javafx/scene/control/ContextMenuTest.java b/modules/javafx.controls/src/test/java/test/javafx/scene/control/ContextMenuTest.java
index 865850a11f9..dd20218f9d6 100644
--- a/modules/javafx.controls/src/test/java/test/javafx/scene/control/ContextMenuTest.java
+++ b/modules/javafx.controls/src/test/java/test/javafx/scene/control/ContextMenuTest.java
@@ -36,6 +36,7 @@
 import static org.junit.jupiter.api.Assertions.assertNull;
 import static org.junit.jupiter.api.Assertions.assertTrue;
 import java.util.Optional;
+import java.util.concurrent.atomic.AtomicInteger;
 import javafx.css.PseudoClass;
 import javafx.event.ActionEvent;
 import javafx.event.EventHandler;
@@ -51,6 +52,7 @@
 import javafx.scene.control.Label;
 import javafx.scene.control.Menu;
 import javafx.scene.control.MenuItem;
+import javafx.scene.control.skin.ButtonSkin;
 import javafx.scene.image.Image;
 import javafx.scene.image.ImageView;
 import javafx.scene.input.KeyCode;
@@ -64,6 +66,7 @@
 import test.com.sun.javafx.scene.control.infrastructure.KeyEventFirer;
 import test.com.sun.javafx.scene.control.infrastructure.MouseEventFirer;
 import test.com.sun.javafx.scene.control.infrastructure.StageLoader;
+import test.javafx.scene.CssStyleHelperTest;
 
 public class ContextMenuTest {
 
@@ -695,6 +698,30 @@ private ContextMenu createContextMenuAndShowSubMenu() {
         assertEquals(anchorBounds.getMinY(), cmBounds.getMinY(), 0.0);
     }
 
+    @Test public void testCssProcessedOnlyOnce() {
+        String css = """
+            .button { -fx-skin: "test.javafx.scene.control.ContextMenuTest$ButtonSkin1"; }
+            .anchor .button { -fx-skin: "st.javafx.scene.control.ContextMenuTest$ButtonSkin2"; }
+            """;
+        anchorBtn.getScene().getStylesheets().add(CssStyleHelperTest.toDataURL(css));
+        anchorBtn.getStyleClass().add("anchor");
+        AtomicInteger skinCounter = new AtomicInteger(0);
+        Button button = new Button();
+        button.skinProperty().subscribe((oldSkin, newSkin) -> {
+            skinCounter.incrementAndGet();
+        });
+        menuItem.setGraphic(button);
+        ContextMenu cm = createContextMenu(false);
+        cm.show(anchorBtn, Side.TOP, 0, 0);
+
+        Bounds anchorBounds = anchorBtn.localToScreen(anchorBtn.getLayoutBounds());
+        Node cmNode = cm.getScene().getRoot();
+        Bounds cmBounds = cm.getScene().getRoot().localToScreen(cmNode.getLayoutBounds());
+
+        assertEquals(anchorBounds.getMinX(), cmBounds.getMinX(), 0.0);
+        assertEquals(anchorBounds.getMinY(), cmBounds.getMaxY(), 0.0);
+        assertEquals(1, skinCounter.get());
+    }
 
     @Test public void test_position_withCSS() {
         anchorBtn.getScene().getStylesheets().add(
@@ -775,4 +802,11 @@ private ContextMenu createContextMenuAndShowSubMenu() {
         assertEquals(0, padding.getLeft(), 0.0);
         anchorBtn.setGraphic(null);
     }
+
+    public static class ButtonSkin1 extends ButtonSkin {
+        public ButtonSkin1(Button button) { super(button); }
+    }
+    public static class ButtonSkin2 extends ButtonSkin {
+        public ButtonSkin2(Button button) { super(button); }
+    }
 }
diff --git a/modules/javafx.graphics/src/main/java/com/sun/javafx/stage/PopupWindowHelper.java b/modules/javafx.graphics/src/main/java/com/sun/javafx/stage/PopupWindowHelper.java
index e7d882ff060..df0e9ab16a0 100644
--- a/modules/javafx.graphics/src/main/java/com/sun/javafx/stage/PopupWindowHelper.java
+++ b/modules/javafx.graphics/src/main/java/com/sun/javafx/stage/PopupWindowHelper.java
@@ -27,6 +27,7 @@
 
 import com.sun.javafx.util.Utils;
 import javafx.collections.ObservableList;
+import javafx.beans.property.ReadOnlyObjectWrapper;
 import javafx.scene.Node;
 import javafx.stage.PopupWindow;
 import javafx.stage.Window;
@@ -67,6 +68,14 @@ public static void applyStylesheetFromOwner(PopupWindow popupWindow, Window owne
         popupWindowAccessor.applyStylesheetFromOwner(popupWindow, owner);
     }
 
+    public static ReadOnlyObjectWrapper<Window> ownerWindow(PopupWindow popupWindow) {
+        return popupWindowAccessor.ownerWindow(popupWindow);
+    }
+
+    public static ReadOnlyObjectWrapper<Node> ownerNode(PopupWindow popupWindow) {
+        return popupWindowAccessor.ownerNode(popupWindow);
+    }
+
     public static ObservableList<Node> getContent(PopupWindow popupWindow) {
         return popupWindowAccessor.getContent(popupWindow);
     }
@@ -84,5 +93,7 @@ public interface PopupWindowAccessor {
         void doVisibleChanging(Window window, boolean visible);
         void doVisibleChanged(Window window, boolean visible);
         void applyStylesheetFromOwner(PopupWindow popupWindow, Window owner);
+        ReadOnlyObjectWrapper<Window> ownerWindow(PopupWindow popupWindow);
+        ReadOnlyObjectWrapper<Node> ownerNode(PopupWindow popupWindow);
     }
 }
diff --git a/modules/javafx.graphics/src/main/java/javafx/stage/PopupWindow.java b/modules/javafx.graphics/src/main/java/javafx/stage/PopupWindow.java
index a7b68f0fa54..c595a8b6955 100644
--- a/modules/javafx.graphics/src/main/java/javafx/stage/PopupWindow.java
+++ b/modules/javafx.graphics/src/main/java/javafx/stage/PopupWindow.java
@@ -121,6 +121,16 @@ public ObservableList<Node> getContent(PopupWindow popupWindow) {
             public void applyStylesheetFromOwner(PopupWindow popupWindow, Window owner) {
                 popupWindow.applyStylesheetFromOwner(owner);
             }
+
+            @Override
+            public ReadOnlyObjectWrapper<Window> ownerWindow(PopupWindow popupWindow) {
+                return popupWindow.ownerWindow;
+            }
+
+            @Override
+            public ReadOnlyObjectWrapper<Node> ownerNode(PopupWindow popupWindow) {
+                return popupWindow.ownerNode;
+            }
         });
     }
 
diff --git a/modules/javafx.graphics/src/test/java/test/javafx/scene/CssStyleHelperTest.java b/modules/javafx.graphics/src/test/java/test/javafx/scene/CssStyleHelperTest.java
index a2e4f46440d..fba61a97a3a 100644
--- a/modules/javafx.graphics/src/test/java/test/javafx/scene/CssStyleHelperTest.java
+++ b/modules/javafx.graphics/src/test/java/test/javafx/scene/CssStyleHelperTest.java
@@ -965,7 +965,7 @@ public void mediaQueryRemovalShouldNotInterruptTransitionsDuringReset() {
         assertEquals(List.of(1.0, 2.0, 1.5, 1.0), trace);
     }
 
-    private static String toDataURL(String stylesheet) {
+    public static String toDataURL(String stylesheet) {
         return "data:text/plain;base64," + Base64.getEncoder().encodeToString(stylesheet.getBytes(StandardCharsets.UTF_8));
     }
 }