diff --git a/examples/components/flutter/macos/Runner/Assets.xcassets/AppIcon.appiconset/app_icon_128.png b/examples/components/flutter/macos/Runner/Assets.xcassets/AppIcon.appiconset/app_icon_128.png
new file mode 100644
index 00000000..13b35eba
Binary files /dev/null and b/examples/components/flutter/macos/Runner/Assets.xcassets/AppIcon.appiconset/app_icon_128.png differ
diff --git a/platform/web/melange/core/lui_web_store.ml b/platform/web/melange/core/lui_web_store.ml
index 0bcd4e43..5fdefaf3 100644
--- a/platform/web/melange/core/lui_web_store.ml
+++ b/platform/web/melange/core/lui_web_store.ml
@@ -27,7 +27,7 @@ let insert_at values inserted_index value =
     invalid_arg "child index is out of bounds";
   let rec loop index rest acc =
     match rest with
-    | [] -> List.rev_append acc [ value ] |> (fun xs -> xs)
+    | [] -> List.rev acc
     | head :: tail ->
         let acc = if index = inserted_index then value :: acc else acc in
         loop (index + 1) tail (head :: acc)
diff --git a/platform/web/melange/popup/lui_web_menu.ml b/platform/web/melange/popup/lui_web_menu.ml
index 97c1319b..20bf0fd3 100644
--- a/platform/web/melange/popup/lui_web_menu.ml
+++ b/platform/web/melange/popup/lui_web_menu.ml
@@ -471,13 +471,53 @@ let attach_picker_trigger_events_bang = attach_picker_trigger_events
 
 (* --- dropdown event wiring --- *)
 
+(* Nested dropdowns are siblings in the DOM (each gets its own positioner in
+   the portal), so a press inside a child submenu is "outside" the parent menu
+   and vice versa. The outside-press check has to consider the whole menu
+   group: walk up through menu-row parents to the root dropdown, then accept a
+   target inside any positioner in that dropdown's subtree. *)
+let rec dropdown_group_root renderer current =
+  match current.retained_parent with
+  | Some parent -> (
+      match Store.node renderer.web_store parent with
+      | Some parent_node when Store.menu_item_row parent_node -> (
+          match parent_node.retained_parent with
+          | Some grandparent -> (
+              match Store.node renderer.web_store grandparent with
+              | Some grandparent_node
+                when Store.standard_kind_is grandparent_node DropdownMenu ->
+                  dropdown_group_root renderer grandparent_node
+              | _ -> current)
+          | None -> current)
+      | _ -> current)
+  | None -> current
+
+let rec group_positioners renderer acc current =
+  let acc =
+    if Store.standard_kind_is current DropdownMenu then
+      current.platform_node :: acc
+    else acc
+  in
+  List.fold_left
+    (fun acc child ->
+      match Store.node renderer.web_store child with
+      | Some child_node -> group_positioners renderer acc child_node
+      | None -> acc)
+    acc current.retained_children
+
 let dropdown_group_contains_event renderer node event =
   match Store.node renderer.web_store node with
   | Some current ->
       let target =
         Lui_web_util.event_target_to_element (W.Event.target event)
       in
-      W.Element.contains (W.Element.asNode target) current.platform_node
+      let group_nodes =
+        group_positioners renderer [] (dropdown_group_root renderer current)
+      in
+      List.exists
+        (fun positioner ->
+          W.Element.contains (W.Element.asNode target) positioner)
+        group_nodes
       ||
       (match current.retained_parent with
        | Some parent ->
@@ -606,8 +646,11 @@ let attach_dropdown_events renderer node _dropdown_node =
         | None -> ())
   in
   let pointer_handler event =
-    if not (dropdown_group_contains_event renderer node event) then
-      emit renderer (Dismiss node);
+    let menu_node = Lui_web_nodes.dom_node renderer node in
+    if
+      W.Element.hasAttribute "data-open" menu_node
+      && not (dropdown_group_contains_event renderer node event)
+    then emit renderer (Dismiss node);
     refresh_position event
   in
   let key_handler event =
diff --git a/platform/web/src/lui.css b/platform/web/src/lui.css
index 3b8f19ce..ecb4bf85 100644
--- a/platform/web/src/lui.css
+++ b/platform/web/src/lui.css
@@ -15,7 +15,7 @@
   --accent-foreground: oklch(0.205 0 0);
   --muted-foreground: oklch(0.556 0 0);
   --destructive: oklch(0.577 0.245 27.325);
-  --destructive-foreground: oklch(0.577 0.245 27.325);
+  --destructive-foreground: oklch(0.985 0 0);
   --error: oklch(0.93 0.0314 17.73);
   --error-foreground: oklch(0.64 0.2082 25.38);
   --success: oklch(0.95 0.0506 162.83);
@@ -574,6 +574,7 @@ body {
   .lui-modal-layer {
     @apply fixed inset-0 isolate;
     z-index: 1000;
+    pointer-events: auto;
   }
 
   .lui-modal-layer[data-ending-style] {