diff --git a/.vscode/settings.json b/.vscode/settings.json
index 4bd8082..c046bca 100644
--- a/.vscode/settings.json
+++ b/.vscode/settings.json
@@ -2,6 +2,8 @@
     "chat.tools.terminal.autoApprove": {
         "mix": true,
         "allium": true,
-        "command": true
+        "command": true,
+        "printf": true,
+        "git ls-tree": true
     }
 }
\ No newline at end of file
diff --git a/lib/bds/desktop/shell_live.ex b/lib/bds/desktop/shell_live.ex
index 4aa239d..7fa13eb 100644
--- a/lib/bds/desktop/shell_live.ex
+++ b/lib/bds/desktop/shell_live.ex
@@ -6,6 +6,7 @@ defmodule BDS.Desktop.ShellLive do
   import Phoenix.HTML
 
   alias BDS.Desktop.{FolderPicker, ShellCommands, ShellData}
+  alias BDS.Desktop.MenuBar, as: DesktopMenuBar
   alias BDS.Git
   alias BDS.Media.Media
   alias BDS.PostLinks
@@ -46,6 +47,9 @@ defmodule BDS.Desktop.ShellLive do
      |> assign(:page_language, ShellData.ui_language())
       |> assign(:client_shortcuts, Commands.client_shortcuts())
      |> assign(:offline_mode, true)
+    |> assign(:is_mac_ui, mac_ui?())
+    |> assign(:menu_groups, titlebar_menu_groups())
+    |> assign(:titlebar_menu_group, nil)
      |> assign(:tab_meta, %{})
       |> assign(:project_menu_open, false)
       |> assign(:sidebar_filters_by_view, %{})
@@ -337,6 +341,33 @@ defmodule BDS.Desktop.ShellLive do
     {:noreply, handle_native_menu_action(socket, action)}
   end
 
+  def handle_event("toggle_titlebar_menu", %{"group" => group}, socket) do
+    next_group = if socket.assigns.titlebar_menu_group == group, do: nil, else: group
+    {:noreply, assign(socket, :titlebar_menu_group, next_group)}
+  end
+
+  def handle_event("hover_titlebar_menu", %{"group" => group}, socket) do
+    socket =
+      if socket.assigns.titlebar_menu_group do
+        assign(socket, :titlebar_menu_group, group)
+      else
+        socket
+      end
+
+    {:noreply, socket}
+  end
+
+  def handle_event("close_titlebar_menu", _params, socket) do
+    {:noreply, assign(socket, :titlebar_menu_group, nil)}
+  end
+
+  def handle_event("titlebar_menu_action", %{"action" => action}, socket) do
+    {:noreply,
+     socket
+     |> assign(:titlebar_menu_group, nil)
+     |> handle_native_menu_action(action)}
+  end
+
   @impl true
   def handle_info(:refresh_task_status, socket) do
     task_status = BDS.Tasks.status_snapshot()
@@ -395,6 +426,7 @@ defmodule BDS.Desktop.ShellLive do
     |> assign(:activity_buttons, activity_buttons)
     |> assign(:panel_tabs, ShellData.panel_tabs(workbench))
     |> assign(:supported_ui_languages, ShellData.supported_ui_languages())
+    |> assign(:menu_groups, socket.assigns[:menu_groups] || titlebar_menu_groups())
     |> assign(:current_tab, current_tab(workbench))
   end
 
@@ -1349,6 +1381,21 @@ defmodule BDS.Desktop.ShellLive do
     |> Enum.map_join(" ", &String.capitalize/1)
   end
 
+  defp titlebar_menu_groups do
+    DesktopMenuBar.groups(dev_mode?: Application.get_env(:bds, :dev_routes, false))
+  end
+
+  defp active_titlebar_menu_group(assigns) do
+    Enum.find(assigns.menu_groups || [], fn group -> Atom.to_string(group.id) == assigns.titlebar_menu_group end)
+  end
+
+  defp mac_ui? do
+    case Application.get_env(:bds, :shell_platform) do
+      nil -> match?({:unix, :darwin}, :os.type())
+      platform -> match?({:unix, :darwin}, platform)
+    end
+  end
+
   defp post_link_entries(assigns) do
     case assigns.current_tab do
       %{type: :post, id: post_id} ->
diff --git a/lib/bds/desktop/shell_live/index.html.heex b/lib/bds/desktop/shell_live/index.html.heex
index 792d9ab..5c50e0f 100644
--- a/lib/bds/desktop/shell_live/index.html.heex
+++ b/lib/bds/desktop/shell_live/index.html.heex
@@ -1,12 +1,29 @@
 <div class="app" id="bds-shell-app" phx-hook="AppShell" data-shortcuts={encoded_shortcuts(@client_shortcuts)}>
-  <div class="window-titlebar" data-region="title-bar">
-    <div class="window-titlebar-menu-bar is-hidden">
-      <button class="window-titlebar-menu-button" type="button">File</button>
-      <button class="window-titlebar-menu-button" type="button">Edit</button>
-      <button class="window-titlebar-menu-button" type="button">View</button>
-      <button class="window-titlebar-menu-button" type="button">Blog</button>
-      <button class="window-titlebar-menu-button" type="button">Help</button>
-    </div>
+  <div
+    class={["window-titlebar", if(@is_mac_ui, do: "is-mac")]}
+    data-region="title-bar"
+    data-testid="window-titlebar"
+    data-open-menu-group={@titlebar_menu_group || ""}
+  >
+    <%= unless @is_mac_ui do %>
+      <div class="window-titlebar-menu-bar" data-testid="window-titlebar-menu-bar">
+        <%= for group <- @menu_groups do %>
+          <button
+            class={[
+              "window-titlebar-menu-button",
+              if(@titlebar_menu_group == Atom.to_string(group.id), do: "is-active")
+            ]}
+            data-testid="window-titlebar-menu-button"
+            data-menu-group={group.id}
+            type="button"
+            phx-click="toggle_titlebar_menu"
+            phx-mouseenter="hover_titlebar_menu"
+            phx-value-group={group.id}
+            aria-label={group.label}
+          ><%= group.label %></button>
+        <% end %>
+      </div>
+    <% end %>
     <div class="window-titlebar-drag-region"></div>
     <div class="window-titlebar-title" data-testid="window-title"><%= @page_title %></div>
     <div class="window-titlebar-actions">
@@ -47,6 +64,36 @@
         </span>
       </button>
     </div>
+    <%= if not @is_mac_ui do %>
+      <%= if group = active_titlebar_menu_group(assigns) do %>
+        <div
+          class="window-titlebar-menu-dropdown"
+          data-testid="window-titlebar-menu-dropdown"
+          phx-click-away="close_titlebar_menu"
+        >
+          <%= for item <- group.items do %>
+            <%= if item.separator do %>
+              <div class="window-titlebar-menu-separator"></div>
+            <% else %>
+              <button
+                class="window-titlebar-menu-item"
+                data-testid="window-titlebar-menu-item"
+                data-menu-action={item.id}
+                type="button"
+                phx-click="titlebar_menu_action"
+                phx-value-action={item.id}
+                aria-label={item.label}
+              >
+                <span class="window-titlebar-menu-item-label"><%= item.label %></span>
+                <%= if item.shortcut do %>
+                  <span class="window-titlebar-menu-item-accelerator"><%= item.shortcut %></span>
+                <% end %>
+              </button>
+            <% end %>
+          <% end %>
+        </div>
+      <% end %>
+    <% end %>
   </div>
 
   <div class="app-main">
diff --git a/priv/ui/app.css b/priv/ui/app.css
index a5d05a0..29eb90b 100644
--- a/priv/ui/app.css
+++ b/priv/ui/app.css
@@ -146,6 +146,10 @@ button {
   background-color: var(--vscode-toolbar-hoverBackground);
 }
 
+.window-titlebar-menu-button.is-active {
+  background-color: var(--vscode-toolbar-hoverBackground);
+}
+
 .window-titlebar-menu-button:focus,
 .window-titlebar-menu-button:focus-visible,
 .window-titlebar-action-button:focus,
@@ -154,6 +158,61 @@ button {
   box-shadow: none;
 }
 
+.window-titlebar-menu-dropdown {
+  position: absolute;
+  top: 30px;
+  left: 6px;
+  min-width: 210px;
+  padding: 6px;
+  display: flex;
+  flex-direction: column;
+  gap: 2px;
+  background-color: var(--vscode-menu-background, var(--vscode-editorWidget-background));
+  border: 1px solid var(--vscode-menu-border, var(--vscode-panel-border));
+  border-radius: 6px;
+  box-shadow: var(--vscode-widget-shadow, 0 8px 24px rgba(0, 0, 0, 0.4));
+  app-region: no-drag;
+  -webkit-app-region: no-drag;
+  z-index: 10;
+}
+
+.window-titlebar-menu-item {
+  border: none;
+  background: transparent;
+  color: var(--vscode-menu-foreground, var(--vscode-foreground));
+  display: flex;
+  align-items: center;
+  justify-content: space-between;
+  gap: 16px;
+  text-align: left;
+  border-radius: 4px;
+  padding: 6px 8px;
+  font-size: 12px;
+  cursor: pointer;
+}
+
+.window-titlebar-menu-item:focus,
+.window-titlebar-menu-item:focus-visible {
+  outline: none;
+  box-shadow: none;
+  background-color: var(--vscode-toolbar-hoverBackground);
+}
+
+.window-titlebar-menu-item:hover,
+.window-titlebar-menu-item.is-keyboard-active {
+  background-color: var(--vscode-menu-selectionBackground, var(--vscode-toolbar-hoverBackground));
+}
+
+.window-titlebar-menu-item-accelerator {
+  opacity: 0.8;
+}
+
+.window-titlebar-menu-separator {
+  height: 1px;
+  margin: 4px 2px;
+  background-color: var(--vscode-menu-separatorBackground, rgba(255, 255, 255, 0.08));
+}
+
 .window-titlebar-drag-region {
   flex: 1;
   height: 100%;
diff --git a/priv/ui/live.js b/priv/ui/live.js
index 43c90f3..79593a2 100644
--- a/priv/ui/live.js
+++ b/priv/ui/live.js
@@ -183,6 +183,27 @@ document.addEventListener("DOMContentLoaded", () => {
           }
         };
 
+        this.menuIsOpen = () => {
+          const titlebar = this.el.querySelector("[data-testid='window-titlebar']");
+          return Boolean(titlebar?.dataset.openMenuGroup);
+        };
+
+        this.handleTitlebarPointerDown = (event) => {
+          if (!this.menuIsOpen()) {
+            return;
+          }
+
+          if (event.target.closest("[data-testid='window-titlebar-menu-button']")) {
+            return;
+          }
+
+          if (event.target.closest("[data-testid='window-titlebar-menu-dropdown']")) {
+            return;
+          }
+
+          this.pushEvent("close_titlebar_menu", {});
+        };
+
         this.handleChange = (event) => {
           const select = event.target.closest(".status-bar-language-select");
 
@@ -216,8 +237,16 @@ document.addEventListener("DOMContentLoaded", () => {
           });
         };
 
+        this.handleEscapeKey = (event) => {
+          if (event.key === "Escape" && this.menuIsOpen()) {
+            this.pushEvent("close_titlebar_menu", {});
+          }
+        };
+
         window.addEventListener("bds:native-menu-action", this.handleNativeMenuAction);
         window.addEventListener("keydown", this.handleShortcutKeyDown, true);
+        window.addEventListener("keydown", this.handleEscapeKey, true);
+        window.addEventListener("pointerdown", this.handleTitlebarPointerDown, true);
         this.el.addEventListener("change", this.handleChange);
       },
 
@@ -226,6 +255,8 @@ document.addEventListener("DOMContentLoaded", () => {
         this.el.removeEventListener("change", this.handleChange);
         window.removeEventListener("bds:native-menu-action", this.handleNativeMenuAction);
         window.removeEventListener("keydown", this.handleShortcutKeyDown, true);
+        window.removeEventListener("keydown", this.handleEscapeKey, true);
+        window.removeEventListener("pointerdown", this.handleTitlebarPointerDown, true);
         if (this.destroyOverlaySync) {
           this.destroyOverlaySync();
         }
diff --git a/test/bds/desktop/shell_live_test.exs b/test/bds/desktop/shell_live_test.exs
index fc1f670..c6b2e56 100644
--- a/test/bds/desktop/shell_live_test.exs
+++ b/test/bds/desktop/shell_live_test.exs
@@ -25,6 +25,16 @@ defmodule BDS.Desktop.ShellLiveTest do
     {:ok, project} = Projects.create_project(%{name: "Shell Project", data_path: temp_dir})
     {:ok, _project} = Projects.set_active_project(project.id)
 
+    original_shell_platform = Application.get_env(:bds, :shell_platform)
+
+    on_exit(fn ->
+      if is_nil(original_shell_platform) do
+        Application.delete_env(:bds, :shell_platform)
+      else
+        Application.put_env(:bds, :shell_platform, original_shell_platform)
+      end
+    end)
+
     %{project: project, temp_dir: temp_dir}
   end
 
@@ -95,6 +105,59 @@ defmodule BDS.Desktop.ShellLiveTest do
     assert html =~ ~s(class="tab-bar-empty")
   end
 
+  test "titlebar menu stays hidden on macos because the native menu owns it" do
+    {:ok, view, html} = live_isolated(build_conn(), BDS.Desktop.ShellLive)
+
+    assert html =~ ~s(class="window-titlebar is-mac")
+    refute html =~ ~s(data-testid="window-titlebar-menu-bar")
+    refute html =~ ~s(data-testid="window-titlebar-menu-button")
+    refute html =~ ~s(data-testid="window-titlebar-menu-dropdown")
+
+    html =
+      render_hook(view, "native_menu_action", %{"action" => "edit_preferences"})
+
+    assert html =~ ~s(data-tab-type="settings")
+    assert html =~ ">Settings<"
+  end
+
+  test "titlebar menu matches the old shell contract on windows and linux" do
+    Application.put_env(:bds, :shell_platform, {:unix, :linux})
+
+    {:ok, view, html} = live_isolated(build_conn(), BDS.Desktop.ShellLive)
+
+    refute html =~ ~s(class="window-titlebar is-mac")
+    assert html =~ ~s(data-testid="window-titlebar-menu-bar")
+    assert html =~ ~s(data-testid="window-titlebar-menu-button")
+    assert html =~ ~s(data-menu-group="file")
+    assert html =~ ~s(>File<)
+
+    html =
+      view
+      |> element("[data-testid='window-titlebar-menu-button'][data-menu-group='file']")
+      |> render_click()
+
+    assert html =~ ~s(data-testid="window-titlebar-menu-dropdown")
+    assert html =~ ~s(data-testid="window-titlebar-menu-item")
+    assert html =~ ~s(data-menu-action="new_post")
+    assert html =~ ~s(>New Post<)
+
+    html =
+      view
+      |> element("[data-testid='window-titlebar-menu-button'][data-menu-group='edit']")
+      |> render_click()
+
+    assert html =~ ~s(data-menu-action="edit_preferences")
+
+    html =
+      view
+      |> element("[data-testid='window-titlebar-menu-item'][data-menu-action='edit_preferences']")
+      |> render_click()
+
+    assert html =~ ~s(data-tab-type="settings")
+    assert html =~ ">Settings<"
+    refute html =~ ~s(data-testid="window-titlebar-menu-dropdown")
+  end
+
   test "sidebar open supports preview and pin intents for entity tabs" do
     {:ok, view, _html} = live_isolated(build_conn(), BDS.Desktop.ShellLive)
 
diff --git a/test/bds/desktop_test.exs b/test/bds/desktop_test.exs
index d504c48..6209455 100644
--- a/test/bds/desktop_test.exs
+++ b/test/bds/desktop_test.exs
@@ -101,7 +101,9 @@ defmodule BDS.DesktopTest do
 
     assert conn.status == 200
     assert conn.resp_body =~ ~s(class="app")
-    assert conn.resp_body =~ ~s(class="window-titlebar")
+    assert conn.resp_body =~ ~s(data-testid="window-titlebar")
+    assert conn.resp_body =~ ~s(class="window-titlebar is-mac")
+    refute conn.resp_body =~ ~s(data-testid="window-titlebar-menu-bar")
     assert conn.resp_body =~ ~s(class="activity-bar")
     assert conn.resp_body =~ ~s(class="sidebar")
     assert conn.resp_body =~ ~s(class="status-bar")