diff --git a/patches/chromium/.patches b/patches/chromium/.patches
index 5f93e351b288..5aa7d95d70fa 100644
--- a/patches/chromium/.patches
+++ b/patches/chromium/.patches
@@ -131,7 +131,7 @@ osr_shared_texture_remove_keyed_mutex_on_win_dxgi.patch
 feat_allow_usage_of_sccontentsharingpicker_on_supported_platforms.patch
 chore_partial_revert_of.patch
 fix_software_compositing_infinite_loop.patch
-fix_add_method_which_disables_headless_mode_on_native_widget.patch
+fix_adjust_headless_mode_handling_in_native_widget.patch
 refactor_unfilter_unresponsive_events.patch
 build_disable_thin_lto_mac.patch
 feat_corner_smoothing_css_rule_and_blink_painting.patch
diff --git a/patches/chromium/fix_add_method_which_disables_headless_mode_on_native_widget.patch b/patches/chromium/fix_adjust_headless_mode_handling_in_native_widget.patch
similarity index 51%
rename from patches/chromium/fix_add_method_which_disables_headless_mode_on_native_widget.patch
rename to patches/chromium/fix_adjust_headless_mode_handling_in_native_widget.patch
index ef21bc45bbe4..f63d0527262c 100644
--- a/patches/chromium/fix_add_method_which_disables_headless_mode_on_native_widget.patch
+++ b/patches/chromium/fix_adjust_headless_mode_handling_in_native_widget.patch
@@ -1,7 +1,7 @@
 From 0000000000000000000000000000000000000000 Mon Sep 17 00:00:00 2001
 From: Cezary Kulakowski <cezary@openfin.co>
 Date: Mon, 22 Jul 2024 16:23:13 +0200
-Subject: fix: add method which disables headless mode on native widget
+Subject: fix: adjust headless mode handling in native widget
 
 We need this method as we create window in headless mode and we
 switch it back to normal mode only after inital paint is done in
@@ -9,8 +9,27 @@ order to get some events like WebContents.beginFrameSubscription.
 If we don't set `is_headless_` to false then some child windows
 e.g. autofill popups will be created in headless mode leading to
 ui problems (like dissapearing popup during typing in html's
-input list.
+input list).
 
+We also need to ensure that an initial paint is scheduled when
+the compositor is unsuspended in headles mode.
+
+diff --git a/ui/views/cocoa/native_widget_mac_ns_window_host.mm b/ui/views/cocoa/native_widget_mac_ns_window_host.mm
+index 7bda1853d47034c80a4e416b9839e8d18c5a8e2c..e5df49253103c44f01195fa93988753fb163d13e 100644
+--- a/ui/views/cocoa/native_widget_mac_ns_window_host.mm
++++ b/ui/views/cocoa/native_widget_mac_ns_window_host.mm
+@@ -659,9 +659,10 @@ void HandleAccelerator(const ui::Accelerator& accelerator,
+   // case it will never become visible but we want its compositor to produce
+   // frames for screenshooting and screencasting.
+   UpdateCompositorProperties();
+-  layer()->SetVisible(is_visible_);
++  layer()->SetVisible(is_visible_ || is_headless_mode_window_);
+   if (is_visible_ || is_headless_mode_window_) {
+     compositor_->Unsuspend();
++    layer()->SchedulePaint(layer()->bounds());
+   }
+ 
+   // Register the CGWindowID (used to identify this window for video capture)
 diff --git a/ui/views/widget/widget.h b/ui/views/widget/widget.h
 index 00113c5a91e4285a102afd37c6c08736d056faf6..f6a719ba09ed9aedc1bdc8322e9bee8d2014fc39 100644
 --- a/ui/views/widget/widget.h
diff --git a/shell/browser/api/electron_api_browser_window.cc b/shell/browser/api/electron_api_browser_window.cc
index 8d92652b033e..742ca07976da 100644
--- a/shell/browser/api/electron_api_browser_window.cc
+++ b/shell/browser/api/electron_api_browser_window.cc
@@ -47,7 +47,7 @@ BrowserWindow::BrowserWindow(gin::Arguments* args,
   // Copy the show setting to webContents, but only if we don't want to paint
   // when initially hidden
   bool paint_when_initially_hidden = true;
-  options.Get("paintWhenInitiallyHidden", &paint_when_initially_hidden);
+  options.Get(options::kPaintWhenInitiallyHidden, &paint_when_initially_hidden);
   if (!paint_when_initially_hidden) {
     bool show = true;
     options.Get(options::kShow, &show);
diff --git a/shell/browser/native_window_mac.mm b/shell/browser/native_window_mac.mm
index f021e6cc742c..8bb7d5b51fa4 100644
--- a/shell/browser/native_window_mac.mm
+++ b/shell/browser/native_window_mac.mm
@@ -154,6 +154,9 @@ NativeWindowMac::NativeWindowMac(const gin_helper::Dictionary& options,
   bool hiddenInMissionControl = false;
   options.Get(options::kHiddenInMissionControl, &hiddenInMissionControl);
 
+  bool paint_when_initially_hidden = true;
+  options.Get(options::kPaintWhenInitiallyHidden, &paint_when_initially_hidden);
+
   // The window without titlebar is treated the same with frameless window.
   if (title_bar_style_ != TitleBarStyle::kNormal)
     set_has_frame(false);
@@ -194,8 +197,8 @@ NativeWindowMac::NativeWindowMac(const gin_helper::Dictionary& options,
   params.bounds = bounds;
   params.delegate = this;
   params.type = views::Widget::InitParams::TYPE_WINDOW;
-  // Allow painting before shown, to be later disabled in ElectronNSWindow.
-  params.headless_mode = true;
+  // Possibly allow painting before shown - later disabled in ElectronNSWindow.
+  params.headless_mode = paint_when_initially_hidden;
   if (IsTranslucent()) {
     params.opacity = views::Widget::InitParams::WindowOpacity::kTranslucent;
   }
diff --git a/shell/common/options_switches.h b/shell/common/options_switches.h
index 6d0895d4cbb3..5bb2284acb4e 100644
--- a/shell/common/options_switches.h
+++ b/shell/common/options_switches.h
@@ -33,6 +33,10 @@ inline constexpr std::string_view kMaximizable = "maximizable";
 inline constexpr std::string_view kFullScreenable = "fullscreenable";
 inline constexpr std::string_view kClosable = "closable";
 
+// Whether to paint when the window is initially hidden.
+inline constexpr std::string_view kPaintWhenInitiallyHidden =
+    "paintWhenInitiallyHidden";
+
 // whether to keep the window out of mission control
 inline constexpr std::string_view kHiddenInMissionControl =
     "hiddenInMissionControl";
diff --git a/spec/api-browser-window-spec.ts b/spec/api-browser-window-spec.ts
index 2e6c7a799550..f90078f9a391 100755
--- a/spec/api-browser-window-spec.ts
+++ b/spec/api-browser-window-spec.ts
@@ -6475,6 +6475,31 @@ describe('BrowserWindow module', () => {
     w.loadFile(path.join(fixtures, 'pages', 'send-after-node.html'));
   });
 
+  // TODO(codebytere): fix on Windows and Linux too
+  ifdescribe(process.platform === 'darwin')('window.webContents initial paint', () => {
+    afterEach(closeAllWindows);
+    it('paints when a window is initially hidden', async () => {
+      const w = new BrowserWindow({ show: false });
+      await w.loadFile(path.join(fixtures, 'pages', 'a.html'));
+
+      const entries = await w.webContents.executeJavaScript(`
+        new Promise((resolve) => {
+          const observer = new PerformanceObserver((performance) => {
+            observer.disconnect();
+            resolve(performance.getEntries());
+          });
+          observer.observe({ entryTypes: ['paint'] });
+        });
+
+        const header = document.createElement('h1');
+        header.innerText = 'Paint me!!';
+        document.getElementById('div').appendChild(header);
+      `);
+
+      expect(JSON.stringify(entries)).to.eq('{}');
+    });
+  });
+
   describe('window.webContents.focus()', () => {
     afterEach(closeAllWindows);
     it('focuses window', async () => {