Index: trunk/src/org/openstreetmap/josm/gui/dialogs/MapPaintDialog.java
===================================================================
--- trunk/src/org/openstreetmap/josm/gui/dialogs/MapPaintDialog.java	(revision 15490)
+++ trunk/src/org/openstreetmap/josm/gui/dialogs/MapPaintDialog.java	(revision 15492)
@@ -37,5 +37,4 @@
 import javax.swing.JMenu;
 import javax.swing.JPanel;
-import javax.swing.JPopupMenu;
 import javax.swing.JScrollPane;
 import javax.swing.JTabbedPane;
@@ -74,4 +73,5 @@
 import org.openstreetmap.josm.gui.util.FileFilterAllFiles;
 import org.openstreetmap.josm.gui.util.GuiHelper;
+import org.openstreetmap.josm.gui.util.StayOpenPopupMenu;
 import org.openstreetmap.josm.gui.widgets.AbstractFileChooser;
 import org.openstreetmap.josm.gui.widgets.FileChooserManager;
@@ -681,5 +681,5 @@
      * The popup menu displayed when right-clicking a map paint entry
      */
-    public class MapPaintPopup extends JPopupMenu {
+    public class MapPaintPopup extends StayOpenPopupMenu {
         /**
          * Constructs a new {@code MapPaintPopup}.
Index: trunk/src/org/openstreetmap/josm/gui/util/StayOpenPopupMenu.java
===================================================================
--- trunk/src/org/openstreetmap/josm/gui/util/StayOpenPopupMenu.java	(revision 15492)
+++ trunk/src/org/openstreetmap/josm/gui/util/StayOpenPopupMenu.java	(revision 15492)
@@ -0,0 +1,89 @@
+// License: GPL. For details, see LICENSE file.
+package org.openstreetmap.josm.gui.util;
+
+import java.awt.AWTEvent;
+import java.awt.Toolkit;
+import java.awt.event.AWTEventListener;
+import java.lang.reflect.Field;
+import java.security.AccessController;
+import java.security.PrivilegedAction;
+import java.util.Map;
+import java.util.Map.Entry;
+import java.util.Objects;
+
+import javax.swing.JPopupMenu;
+import javax.swing.MenuSelectionManager;
+import javax.swing.event.ChangeListener;
+
+import org.openstreetmap.josm.tools.Logging;
+import org.openstreetmap.josm.tools.PlatformManager;
+import org.openstreetmap.josm.tools.ReflectionUtils;
+
+/**
+ * A {@link JPopupMenu} that can stay open on all platforms when containing {@code StayOpen*} items.
+ * @since 15492
+ */
+public class StayOpenPopupMenu extends JPopupMenu {
+
+    private static final String MOUSE_GRABBER_KEY = "javax.swing.plaf.basic.BasicPopupMenuUI.MouseGrabber";
+
+    /**
+     * Special mask for the UngrabEvent events, in addition to the public masks defined in AWTEvent.
+     */
+    private static final int GRAB_EVENT_MASK = 0x80000000;
+
+    /**
+     * Constructs a new {@code StayOpenPopupMenu}.
+     */
+    public StayOpenPopupMenu() {
+    }
+
+    /**
+     * Constructs a new {@code StayOpenPopupMenu} with the specified title.
+     * @param label  the string that a UI may use to display as a title for the popup menu.
+     */
+    public StayOpenPopupMenu(String label) {
+        super(label);
+    }
+
+    @Override
+    public void setVisible(boolean b) {
+        // macOS triggers a spurious UngrabEvent that is catched by BasicPopupMenuUI.MouseGrabber
+        // and makes the popup menu disappear. Probably related to https://bugs.openjdk.java.net/browse/JDK-8225698
+        if (PlatformManager.isPlatformOsx()) {
+            try {
+                Class<?> AppContextClass = Class.forName("sun.awt.AppContext");
+                Field tableField = AppContextClass.getDeclaredField("table");
+                ReflectionUtils.setObjectsAccessible(tableField);
+                Object mouseGrabber = null;
+                for (Entry<?, ?> e : ((Map<?, ?>)
+                        tableField.get(AppContextClass.getMethod("getAppContext").invoke(AppContextClass))).entrySet()) {
+                    if (MOUSE_GRABBER_KEY.equals(Objects.toString(e.getKey()))) {
+                        mouseGrabber = e.getValue();
+                        break;
+                    }
+                }
+                final ChangeListener changeListener = (ChangeListener) mouseGrabber;
+                final AWTEventListener awtEventListener = (AWTEventListener) mouseGrabber;
+                final MenuSelectionManager msm = MenuSelectionManager.defaultManager();
+                final Toolkit tk = Toolkit.getDefaultToolkit();
+                AccessController.doPrivileged((PrivilegedAction<Object>) () -> {
+                    if (b)
+                        msm.removeChangeListener(changeListener);
+                    else
+                        msm.addChangeListener(changeListener);
+                    tk.removeAWTEventListener(awtEventListener);
+                    tk.addAWTEventListener(awtEventListener,
+                            AWTEvent.MOUSE_EVENT_MASK |
+                            AWTEvent.MOUSE_MOTION_EVENT_MASK |
+                            AWTEvent.MOUSE_WHEEL_EVENT_MASK |
+                            AWTEvent.WINDOW_EVENT_MASK | (b ? 0 : GRAB_EVENT_MASK));
+                    return null;
+                });
+            } catch (ReflectiveOperationException | RuntimeException e) {
+                Logging.error(e);
+            }
+        }
+        super.setVisible(b);
+    }
+}