diff --git a/src/plugins/platforms/cocoa/qcocoamenu.mm b/src/plugins/platforms/cocoa/qcocoamenu.mm
index 566363e01f..88ffd48538 100644
--- a/src/plugins/platforms/cocoa/qcocoamenu.mm
+++ b/src/plugins/platforms/cocoa/qcocoamenu.mm
@@ -147,6 +147,10 @@ QT_NAMESPACE_ALIAS_OBJC_CLASS(QCocoaMenuDelegate);
 - (void) itemFired:(NSMenuItem*) item
 {
     QCocoaMenuItem *cocoaItem = reinterpret_cast<QCocoaMenuItem *>([item tag]);
+    // Menu-holding items also get a target to play nicely
+    // with NSMenuValidation but should not trigger.
+    if (cocoaItem->menu())
+        return;
     QScopedScopeLevelCounter scopeLevelCounter(QGuiApplicationPrivate::instance()->threadData);
     QGuiApplicationPrivate::modifier_buttons = [QNSView convertKeyModifiers:[NSEvent modifierFlags]];
     static QMetaMethod activatedSignal = QMetaMethod::fromSignal(&QCocoaMenuItem::activated);
@@ -156,7 +160,8 @@ QT_NAMESPACE_ALIAS_OBJC_CLASS(QCocoaMenuDelegate);
 - (BOOL)validateMenuItem:(NSMenuItem*)menuItem
 {
     QCocoaMenuItem *cocoaItem = reinterpret_cast<QCocoaMenuItem *>(menuItem.tag);
-    if (!cocoaItem)
+    // Menu-holding items are always enabled, as it's conventional in Cocoa
+    if (!cocoaItem || cocoaItem->menu())
         return YES;
 
     return cocoaItem->isEnabled();
@@ -327,9 +332,9 @@ void QCocoaMenu::insertMenuItem(QPlatformMenuItem *menuItem, QPlatformMenuItem *
 void QCocoaMenu::insertNative(QCocoaMenuItem *item, QCocoaMenuItem *beforeItem)
 {
     item->nsItem().target = m_nativeMenu.delegate;
-    if (!item->menu())
-        [item->nsItem() setAction:@selector(itemFired:)];
-    else if (isOpen() && item->nsItem()) // Someone's adding new items after aboutToShow() was emitted
+    item->nsItem().action = @selector(itemFired:);
+    // Someone's adding new items after aboutToShow() was emitted
+    if (isOpen() && item->menu() && item->nsItem())
         item->menu()->setAttachedItem(item->nsItem());
 
     item->setParentEnabled(isEnabled());
@@ -425,6 +430,10 @@ void QCocoaMenu::syncMenuItem(QPlatformMenuItem *menuItem)
 
         QCocoaMenuItem* beforeItem = itemOrNull(m_menuItems.indexOf(cocoaItem) + 1);
         insertNative(cocoaItem, beforeItem);
+    } else {
+        // Force NSMenuValidation to kick in. This is needed e.g.
+        // when an item's enabled state changes after menuWillOpen:
+        [m_nativeMenu update];
     }
 }
 
diff --git a/tests/manual/cocoa/menurama/mainwindow.cpp b/tests/manual/cocoa/menurama/mainwindow.cpp
index db8fdafc21..f7762f57f5 100644
--- a/tests/manual/cocoa/menurama/mainwindow.cpp
+++ b/tests/manual/cocoa/menurama/mainwindow.cpp
@@ -56,7 +56,13 @@ MainWindow::MainWindow(QWidget *parent) :
     });
 
     connect(ui->menuDynamic_Stuff, &QMenu::aboutToShow, [=] {
-        menuApp->addDynMenu(QLatin1String("Added After aboutToShow()"), ui->menuDynamic_Stuff);
+        menuApp->addDynMenu(QLatin1String("Menu Added After aboutToShow()"), ui->menuDynamic_Stuff);
+
+        const QLatin1String itemTitle = QLatin1String("Disabled Item Added After aboutToShow()");
+        if (QAction *a = menuApp->findAction(itemTitle, ui->menuDynamic_Stuff))
+            ui->menuDynamic_Stuff->removeAction(a);
+        QAction *a = ui->menuDynamic_Stuff->addAction(itemTitle);
+        a->setEnabled(false);
     });
 
     connect(ui->pushButton, &QPushButton::clicked, [=] {
diff --git a/tests/manual/cocoa/menurama/mainwindow.ui b/tests/manual/cocoa/menurama/mainwindow.ui
index f73b41b861..d3caa6c608 100644
--- a/tests/manual/cocoa/menurama/mainwindow.ui
+++ b/tests/manual/cocoa/menurama/mainwindow.ui
@@ -6,63 +6,71 @@
    <rect>
     <x>0</x>
     <y>0</y>
-    <width>566</width>
-    <height>300</height>
+    <width>429</width>
+    <height>251</height>
    </rect>
   </property>
   <property name="windowTitle">
    <string>MainWindow</string>
   </property>
   <widget class="QWidget" name="centralWidget">
-   <widget class="QCheckBox" name="checkBox">
-    <property name="geometry">
-     <rect>
-      <x>10</x>
-      <y>40</y>
-      <width>151</width>
-      <height>20</height>
-     </rect>
-    </property>
-    <property name="text">
-     <string>Enable &quot;Stuff&quot; Menu</string>
-    </property>
-    <property name="checked">
-     <bool>true</bool>
-    </property>
-   </widget>
-   <widget class="QLabel" name="label">
-    <property name="geometry">
-     <rect>
-      <x>10</x>
-      <y>10</y>
-      <width>321</width>
-      <height>16</height>
-     </rect>
-    </property>
-    <property name="text">
-     <string>The &quot;Help&quot; menu should NOT be visible.</string>
-    </property>
-   </widget>
-   <widget class="QPushButton" name="pushButton">
-    <property name="geometry">
-     <rect>
-      <x>10</x>
-      <y>80</y>
-      <width>211</width>
-      <height>32</height>
-     </rect>
-    </property>
-    <property name="text">
-     <string>Populate Dynamic Submenu</string>
-    </property>
-   </widget>
+   <layout class="QVBoxLayout" name="verticalLayout_2">
+    <item>
+     <layout class="QVBoxLayout" name="verticalLayout">
+      <property name="spacing">
+       <number>24</number>
+      </property>
+      <item>
+       <widget class="QLabel" name="label">
+        <property name="text">
+         <string>The &quot;Help&quot; menu should NOT be visible.
+
+Click on &quot;Dynamic Stuff&quot; then move left and right to other menus. Disabled items should remain that way.</string>
+        </property>
+        <property name="scaledContents">
+         <bool>false</bool>
+        </property>
+        <property name="alignment">
+         <set>Qt::AlignLeading|Qt::AlignLeft|Qt::AlignTop</set>
+        </property>
+        <property name="wordWrap">
+         <bool>true</bool>
+        </property>
+       </widget>
+      </item>
+      <item>
+       <widget class="QCheckBox" name="checkBox">
+        <property name="text">
+         <string>Enable &quot;Stuff&quot; Menu</string>
+        </property>
+        <property name="checked">
+         <bool>true</bool>
+        </property>
+       </widget>
+      </item>
+      <item>
+       <widget class="QPushButton" name="pushButton">
+        <property name="sizePolicy">
+         <sizepolicy hsizetype="Maximum" vsizetype="Fixed">
+          <horstretch>0</horstretch>
+          <verstretch>0</verstretch>
+         </sizepolicy>
+        </property>
+        <property name="text">
+         <string>Populate Dynamic Submenu</string>
+        </property>
+       </widget>
+      </item>
+     </layout>
+    </item>
+   </layout>
   </widget>
   <widget class="QMenuBar" name="menuBar">
    <property name="geometry">
     <rect>
      <x>0</x>
      <y>0</y>
-     <width>566</width>
+     <width>429</width>
      <height>22</height>
     </rect>
    </property>
diff --git a/tests/manual/cocoa/menurama/menuramaapplication.cpp b/tests/manual/cocoa/menurama/menuramaapplication.cpp
index 534d5fa371..13e457d7dd 100644
--- a/tests/manual/cocoa/menurama/menuramaapplication.cpp
+++ b/tests/manual/cocoa/menurama/menuramaapplication.cpp
@@ -69,13 +69,19 @@ void MenuramaApplication::populateMenu(QMenu *menu, bool clear)
 
 void MenuramaApplication::addDynMenu(QLatin1String title, QMenu *parentMenu)
 {
-    foreach (QAction *a, parentMenu->actions())
-        if (a->text() == title) {
-            parentMenu->removeAction(a);
-            break;
-        }
+    if (QAction *a = findAction(title, parentMenu))
+        parentMenu->removeAction(a);
 
     QMenu *subMenu = new QMenu(title, parentMenu);
     populateMenu(subMenu, false /*clear*/);
     parentMenu->addMenu(subMenu);
 }
+
+QAction *MenuramaApplication::findAction(QLatin1String title, QMenu *parentMenu)
+{
+    foreach (QAction *a, parentMenu->actions())
+        if (a->text() == title)
+            return a;
+
+    return Q_NULLPTR;
+}
diff --git a/tests/manual/cocoa/menurama/menuramaapplication.h b/tests/manual/cocoa/menurama/menuramaapplication.h
index 07c8da27a1..b0670cc53b 100644
--- a/tests/manual/cocoa/menurama/menuramaapplication.h
+++ b/tests/manual/cocoa/menurama/menuramaapplication.h
@@ -50,6 +50,7 @@ class MenuramaApplication : public QApplication
 public:
     MenuramaApplication(int argc, char **argv);
     void addDynMenu(QLatin1String title, QMenu *parentMenu);
+    QAction *findAction(QLatin1String title, QMenu *parentMenu);
 
 public slots:
     void populateMenu(QMenu *menu, bool clear);