diff --git a/shell/browser/ui/cocoa/electron_menu_controller.mm b/shell/browser/ui/cocoa/electron_menu_controller.mm
index d23e007dd0ba..2c5eae1499b1 100644
--- a/shell/browser/ui/cocoa/electron_menu_controller.mm
+++ b/shell/browser/ui/cocoa/electron_menu_controller.mm
@@ -320,6 +320,10 @@ NSArray* ConvertSharingItemToNS(const SharingItem& item) {
   NSMenuItem* item = [[NSMenuItem alloc] initWithTitle:label
                                                 action:@selector(itemSelected:)
                                          keyEquivalent:@""];
+  if (model->IsEnabledAt(index))
+    [item setEnabled:YES];
+  else
+    [item setEnabled:NO];
 
   // If the menu item has an icon, set it.
   ui::ImageModel icon = model->GetIconAt(index);
@@ -349,11 +353,6 @@ NSArray* ConvertSharingItemToNS(const SharingItem& item) {
     [item setSubmenu:[self createShareMenuForItem:sharing_item]];
   } else if (type == electron::ElectronMenuModel::TYPE_SUBMENU &&
              model->IsVisibleAt(index)) {
-    // We need to specifically check that the submenu top-level item has been
-    // enabled as it's not validated by validateUserInterfaceItem
-    if (!model->IsEnabledAt(index))
-      [item setEnabled:NO];
-
     // Recursively build a submenu from the sub-model at this index.
     [item setTarget:nil];
     [item setAction:nil];
@@ -493,8 +492,10 @@ NSArray* ConvertSharingItemToNS(const SharingItem& item) {
 }
 
 - (NSMenu*)menu {
-  if (menu_)
+  if (menu_) {
+    [menu_ setAutoenablesItems:NO];
     return menu_;
+  }
 
   if (model_ && model_->sharing_item()) {
     NSMenu* menu = [self createShareMenuForItem:*model_->sharing_item()];
@@ -504,6 +505,8 @@ NSArray* ConvertSharingItemToNS(const SharingItem& item) {
     if (model_)
       [self populateWithModel:model_.get()];
   }
+
+  [menu_ setAutoenablesItems:NO];
   [menu_ setDelegate:self];
   return menu_;
 }