diff --git a/patches/chromium/.patches b/patches/chromium/.patches
index f07d408448..90cc77fa80 100644
--- a/patches/chromium/.patches
+++ b/patches/chromium/.patches
@@ -129,5 +129,4 @@ chore_patch_out_profile_methods_in_titlebar_config.patch
 fix_crash_on_nativetheme_change_during_context_menu_close.patch
 fix_select_the_first_menu_item_when_opened_via_keyboard.patch
 fix_return_v8_value_from_localframe_requestexecutescript.patch
-revert_simplify_dwm_transitions_on_windows.patch
 fix_harden_blink_scriptstate_maybefrom.patch
diff --git a/patches/chromium/revert_simplify_dwm_transitions_on_windows.patch b/patches/chromium/revert_simplify_dwm_transitions_on_windows.patch
deleted file mode 100644
index 63cd6ffa47..0000000000
--- a/patches/chromium/revert_simplify_dwm_transitions_on_windows.patch
+++ /dev/null
@@ -1,368 +0,0 @@
-From 0000000000000000000000000000000000000000 Mon Sep 17 00:00:00 2001
-From: deepak1556 <hop2deep@gmail.com>
-Date: Tue, 27 Jun 2023 22:05:17 +0900
-Subject: Revert "Simplify DWM transitions on Windows"
-
-This reverts commit 392e5f43aae8d225a118145cbc5f5bb104cbe541.
-
-Can be removed once https://github.com/electron/electron/issues/38937 is resolved.
-
-diff --git a/chrome/app/chrome_command_ids.h b/chrome/app/chrome_command_ids.h
-index 15f4aac24744228c0e74ec521c18eb6ab5f59c5b..b9a71c9063d8ee573424a9161cc127af169944a9 100644
---- a/chrome/app/chrome_command_ids.h
-+++ b/chrome/app/chrome_command_ids.h
-@@ -59,6 +59,7 @@
- #define IDC_MOVE_TAB_NEXT               34032
- #define IDC_MOVE_TAB_PREVIOUS           34033
- #define IDC_SEARCH                      34035
-+#define IDC_DEBUG_FRAME_TOGGLE          34038
- #define IDC_WINDOW_MENU                 34045
- #define IDC_MINIMIZE_WINDOW             34046
- #define IDC_MAXIMIZE_WINDOW             34047
-diff --git a/chrome/browser/ui/browser_command_controller.cc b/chrome/browser/ui/browser_command_controller.cc
-index b198e41661d459302ddccfab70ac3de8cd2c48b5..405c0ac7c41ef4cb6a8804c8a34a7328d796d7bd 100644
---- a/chrome/browser/ui/browser_command_controller.cc
-+++ b/chrome/browser/ui/browser_command_controller.cc
-@@ -1184,6 +1184,7 @@ void BrowserCommandController::InitCommandState() {
-       IDC_DUPLICATE_TAB, !browser_->is_type_picture_in_picture());
-   UpdateTabRestoreCommandState();
-   command_updater_.UpdateCommandEnabled(IDC_EXIT, true);
-+  command_updater_.UpdateCommandEnabled(IDC_DEBUG_FRAME_TOGGLE, true);
-   command_updater_.UpdateCommandEnabled(IDC_NAME_WINDOW, true);
- #if BUILDFLAG(IS_CHROMEOS)
-   command_updater_.UpdateCommandEnabled(
-diff --git a/chrome/browser/ui/views/frame/browser_desktop_window_tree_host_win.cc b/chrome/browser/ui/views/frame/browser_desktop_window_tree_host_win.cc
-index fa718692b769c3bbcf83f700718cf88dc631d058..c8ed066b698ab08d5cfbc644ca1f66f23c0fbeec 100644
---- a/chrome/browser/ui/views/frame/browser_desktop_window_tree_host_win.cc
-+++ b/chrome/browser/ui/views/frame/browser_desktop_window_tree_host_win.cc
-@@ -397,6 +397,13 @@ void BrowserDesktopWindowTreeHostWin::HandleDestroying() {
-   DesktopWindowTreeHostWin::HandleDestroying();
- }
- 
-+void BrowserDesktopWindowTreeHostWin::HandleFrameChanged() {
-+  // Reinitialize the status bubble, since it needs to be initialized
-+  // differently depending on whether or not DWM composition is enabled
-+  browser_view_->InitStatusBubble();
-+  DesktopWindowTreeHostWin::HandleFrameChanged();
-+}
-+
- void BrowserDesktopWindowTreeHostWin::HandleWindowScaleFactorChanged(
-     float window_scale_factor) {
-   DesktopWindowTreeHostWin::HandleWindowScaleFactorChanged(window_scale_factor);
-diff --git a/chrome/browser/ui/views/frame/browser_desktop_window_tree_host_win.h b/chrome/browser/ui/views/frame/browser_desktop_window_tree_host_win.h
-index 28412d00adf463a1453aecc82ca1179f0521822d..a3bd2e0cae1d341adfe9dd498886ae5914e1cba7 100644
---- a/chrome/browser/ui/views/frame/browser_desktop_window_tree_host_win.h
-+++ b/chrome/browser/ui/views/frame/browser_desktop_window_tree_host_win.h
-@@ -66,6 +66,7 @@ class BrowserDesktopWindowTreeHostWin
-   bool GetDwmFrameInsetsInPixels(gfx::Insets* insets) const override;
-   void HandleCreate() override;
-   void HandleDestroying() override;
-+  void HandleFrameChanged() override;
-   void HandleWindowScaleFactorChanged(float window_scale_factor) override;
-   bool PreHandleMSG(UINT message,
-                     WPARAM w_param,
-diff --git a/chrome/browser/ui/views/frame/browser_view.cc b/chrome/browser/ui/views/frame/browser_view.cc
-index 6920106ba91e0d1c0c1706a28b4ce5a14b5f3aed..306affc1d9573acd475d79f30a3583f0e716f33e 100644
---- a/chrome/browser/ui/views/frame/browser_view.cc
-+++ b/chrome/browser/ui/views/frame/browser_view.cc
-@@ -927,8 +927,7 @@ BrowserView::BrowserView(std::unique_ptr<Browser> browser)
-   infobar_container_ =
-       AddChildView(std::make_unique<InfoBarContainerView>(this));
- 
--  status_bubble_ = std::make_unique<StatusBubbleViews>(contents_web_view_);
--  contents_web_view_->SetStatusBubble(status_bubble_.get());
-+  InitStatusBubble();
- 
-   // Create do-nothing view for the sake of controlling the z-order of the find
-   // bar widget.
-@@ -1049,6 +1048,11 @@ void BrowserView::SetDisableRevealerDelayForTesting(bool disable) {
-   g_disable_revealer_delay_for_testing = disable;
- }
- 
-+void BrowserView::InitStatusBubble() {
-+  status_bubble_ = std::make_unique<StatusBubbleViews>(contents_web_view_);
-+  contents_web_view_->SetStatusBubble(status_bubble_.get());
-+}
-+
- gfx::Rect BrowserView::GetFindBarBoundingBox() const {
-   gfx::Rect contents_bounds = contents_container_->ConvertRectToWidget(
-       contents_container_->GetLocalBounds());
-@@ -3397,6 +3401,11 @@ ui::ImageModel BrowserView::GetWindowIcon() {
- }
- 
- bool BrowserView::ExecuteWindowsCommand(int command_id) {
-+  // This function handles WM_SYSCOMMAND, WM_APPCOMMAND, and WM_COMMAND.
-+#if BUILDFLAG(IS_WIN)
-+  if (command_id == IDC_DEBUG_FRAME_TOGGLE)
-+    GetWidget()->DebugToggleFrameType();
-+#endif
-   // Translate WM_APPCOMMAND command ids into a command id that the browser
-   // knows how to handle.
-   int command_id_from_app_command = GetCommandIDForAppCommandID(command_id);
-diff --git a/chrome/browser/ui/views/frame/browser_view.h b/chrome/browser/ui/views/frame/browser_view.h
-index d80a6df7380e5aec6ecba092315c905a09d7e2cc..bde91001c6f75f9918b9063eb0eaff5d56ea06c1 100644
---- a/chrome/browser/ui/views/frame/browser_view.h
-+++ b/chrome/browser/ui/views/frame/browser_view.h
-@@ -164,6 +164,12 @@ class BrowserView : public BrowserWindow,
- 
-   void SetDownloadShelfForTest(DownloadShelf* download_shelf);
- 
-+  // Initializes (or re-initializes) the status bubble.  We try to only create
-+  // the bubble once and re-use it for the life of the browser, but certain
-+  // events (such as changing enabling/disabling Aero on Win) can force a need
-+  // to change some of the bubble's creation parameters.
-+  void InitStatusBubble();
-+
-   // Returns the constraining bounding box that should be used to lay out the
-   // FindBar within. This is _not_ the size of the find bar, just the bounding
-   // box it should be laid out within. The coordinate system of the returned
-diff --git a/chrome/browser/ui/views/frame/system_menu_model_builder.cc b/chrome/browser/ui/views/frame/system_menu_model_builder.cc
-index 984929bb899dbd791443bf3ccd841f5a975a7dbd..75719ef6280ce46c176cb3277e602a11d99a45e0 100644
---- a/chrome/browser/ui/views/frame/system_menu_model_builder.cc
-+++ b/chrome/browser/ui/views/frame/system_menu_model_builder.cc
-@@ -69,6 +69,7 @@ void SystemMenuModelBuilder::BuildMenu(ui::SimpleMenuModel* model) {
-     BuildSystemMenuForBrowserWindow(model);
-   else
-     BuildSystemMenuForAppOrPopupWindow(model);
-+  AddFrameToggleItems(model);
- }
- 
- void SystemMenuModelBuilder::BuildSystemMenuForBrowserWindow(
-@@ -157,6 +158,14 @@ void SystemMenuModelBuilder::BuildSystemMenuForAppOrPopupWindow(
-   AppendTeleportMenu(model);
- }
- 
-+void SystemMenuModelBuilder::AddFrameToggleItems(ui::SimpleMenuModel* model) {
-+  if (base::CommandLine::ForCurrentProcess()->HasSwitch(
-+          switches::kDebugEnableFrameToggle)) {
-+    model->AddSeparator(ui::NORMAL_SEPARATOR);
-+    model->AddItem(IDC_DEBUG_FRAME_TOGGLE, u"Toggle Frame Type");
-+  }
-+}
-+
- #if BUILDFLAG(IS_CHROMEOS)
- void SystemMenuModelBuilder::AppendMoveToDesksMenu(ui::SimpleMenuModel* model) {
-   gfx::NativeWindow window =
-diff --git a/chrome/browser/ui/views/frame/system_menu_model_builder.h b/chrome/browser/ui/views/frame/system_menu_model_builder.h
-index 8f69eab1fc2b9c81d14f7b547b4f434c722b98aa..8acaa2816a03f41b19ec364eea2658682737798c 100644
---- a/chrome/browser/ui/views/frame/system_menu_model_builder.h
-+++ b/chrome/browser/ui/views/frame/system_menu_model_builder.h
-@@ -47,6 +47,9 @@ class SystemMenuModelBuilder {
-   void BuildSystemMenuForBrowserWindow(ui::SimpleMenuModel* model);
-   void BuildSystemMenuForAppOrPopupWindow(ui::SimpleMenuModel* model);
- 
-+  // Adds items for toggling the frame type (if necessary).
-+  void AddFrameToggleItems(ui::SimpleMenuModel* model);
-+
- #if BUILDFLAG(IS_CHROMEOS)
-   // Add the submenu for move to desks.
-   void AppendMoveToDesksMenu(ui::SimpleMenuModel* model);
-diff --git a/chrome/common/chrome_switches.cc b/chrome/common/chrome_switches.cc
-index b23fbffea35f1f9936b998bbe501c9e5acdecf6a..4d635764d6c5db0b493aba9d3b2add095fc9ebe4 100644
---- a/chrome/common/chrome_switches.cc
-+++ b/chrome/common/chrome_switches.cc
-@@ -143,6 +143,10 @@ const char kCredits[] = "credits";
- // devtools://devtools/bundled/<path>
- const char kCustomDevtoolsFrontend[] = "custom-devtools-frontend";
- 
-+// Enables a frame context menu item that toggles the frame in and out of glass
-+// mode (Windows Vista and up only).
-+const char kDebugEnableFrameToggle[] = "debug-enable-frame-toggle";
-+
- // Adds debugging entries such as Inspect Element to context menus of packed
- // apps.
- const char kDebugPackedApps[] = "debug-packed-apps";
-diff --git a/chrome/common/chrome_switches.h b/chrome/common/chrome_switches.h
-index be1f7824d85a6705aa8c220578ac62f0d1a4114e..7ce3dd85d1cab1fbd5aff6104ea0d1b864ebcb0c 100644
---- a/chrome/common/chrome_switches.h
-+++ b/chrome/common/chrome_switches.h
-@@ -61,6 +61,7 @@ extern const char kCrashOnHangThreads[];
- extern const char kCreateBrowserOnStartupForTests[];
- extern const char kCredits[];
- extern const char kCustomDevtoolsFrontend[];
-+extern const char kDebugEnableFrameToggle[];
- extern const char kDebugPackedApps[];
- extern const char kDevToolsFlags[];
- extern const char kDiagnostics[];
-diff --git a/ui/views/widget/desktop_aura/desktop_native_widget_aura_unittest.cc b/ui/views/widget/desktop_aura/desktop_native_widget_aura_unittest.cc
-index d0dc2b4993891837c6ac76e095833126db461032..ba1bcbc63475b7151e2335c9237124ca8ca31dc7 100644
---- a/ui/views/widget/desktop_aura/desktop_native_widget_aura_unittest.cc
-+++ b/ui/views/widget/desktop_aura/desktop_native_widget_aura_unittest.cc
-@@ -136,6 +136,30 @@ TEST_F(DesktopNativeWidgetAuraTest, WidgetNotVisibleOnlyWindowTreeHostShown) {
- }
- #endif
- 
-+TEST_F(DesktopNativeWidgetAuraTest, DesktopAuraWindowShowFrameless) {
-+  Widget widget;
-+  Widget::InitParams init_params =
-+      CreateParams(Widget::InitParams::TYPE_WINDOW_FRAMELESS);
-+  init_params.ownership = Widget::InitParams::WIDGET_OWNS_NATIVE_WIDGET;
-+  widget.Init(std::move(init_params));
-+
-+  // Make sure that changing frame type doesn't crash when there's no non-client
-+  // view.
-+  ASSERT_EQ(nullptr, widget.non_client_view());
-+  widget.DebugToggleFrameType();
-+  widget.Show();
-+
-+#if BUILDFLAG(IS_WIN)
-+  // On Windows also make sure that handling WM_SYSCOMMAND doesn't crash with
-+  // custom frame. Frame type needs to be toggled again if Aero Glass is
-+  // disabled.
-+  if (widget.ShouldUseNativeFrame())
-+    widget.DebugToggleFrameType();
-+  SendMessage(widget.GetNativeWindow()->GetHost()->GetAcceleratedWidget(),
-+              WM_SYSCOMMAND, SC_RESTORE, 0);
-+#endif  // BUILDFLAG(IS_WIN)
-+}
-+
- #if BUILDFLAG(IS_CHROMEOS_ASH)
- // TODO(crbug.com/916272): investigate fixing and enabling on Chrome OS.
- #define MAYBE_GlobalCursorState DISABLED_GlobalCursorState
-diff --git a/ui/views/widget/desktop_aura/desktop_window_tree_host_win.cc b/ui/views/widget/desktop_aura/desktop_window_tree_host_win.cc
-index 73e76c0d940f09336bbec6db47f1afee5153ced0..61673ac08ca19816dc01c89b6687f5b2a7c289e2 100644
---- a/ui/views/widget/desktop_aura/desktop_window_tree_host_win.cc
-+++ b/ui/views/widget/desktop_aura/desktop_window_tree_host_win.cc
-@@ -1028,6 +1028,8 @@ void DesktopWindowTreeHostWin::HandleClientSizeChanged(
- }
- 
- void DesktopWindowTreeHostWin::HandleFrameChanged() {
-+  CheckForMonitorChange();
-+  desktop_native_widget_aura_->UpdateWindowTransparency();
-   // Replace the frame and layout the contents.
-   if (GetWidget()->non_client_view())
-     GetWidget()->non_client_view()->UpdateFrame();
-diff --git a/ui/views/widget/widget.cc b/ui/views/widget/widget.cc
-index 2b52ad2f63bd6924fcd3d000bbb7ed6fd9f4b0dd..3d7a2f986c38de6b2e69722e63ee3b139d257756 100644
---- a/ui/views/widget/widget.cc
-+++ b/ui/views/widget/widget.cc
-@@ -1209,6 +1209,21 @@ bool Widget::ShouldWindowContentsBeTransparent() const {
-                         : false;
- }
- 
-+void Widget::DebugToggleFrameType() {
-+  if (!native_widget_)
-+    return;
-+
-+  if (frame_type_ == FrameType::kDefault) {
-+    frame_type_ = ShouldUseNativeFrame() ? FrameType::kForceCustom
-+                                         : FrameType::kForceNative;
-+  } else {
-+    frame_type_ = frame_type_ == FrameType::kForceCustom
-+                      ? FrameType::kForceNative
-+                      : FrameType::kForceCustom;
-+  }
-+  FrameTypeChanged();
-+}
-+
- void Widget::FrameTypeChanged() {
-   if (native_widget_)
-     native_widget_->FrameTypeChanged();
-diff --git a/ui/views/widget/widget.h b/ui/views/widget/widget.h
-index 51017b6f5dd9a9d5f26723c7ec7a6e0404c93b65..54b9e676c9423b78184fc63b80299dd7529cbd28 100644
---- a/ui/views/widget/widget.h
-+++ b/ui/views/widget/widget.h
-@@ -922,6 +922,10 @@ class VIEWS_EXPORT Widget : public internal::NativeWidgetDelegate,
-   // (for example, so that they can overhang onto the window title bar).
-   bool ShouldWindowContentsBeTransparent() const;
- 
-+  // Forces the frame into the alternate frame type (custom or native) depending
-+  // on its current state.
-+  void DebugToggleFrameType();
-+
-   // Tell the window that something caused the frame type to change.
-   void FrameTypeChanged();
- 
-diff --git a/ui/views/widget/widget_unittest.cc b/ui/views/widget/widget_unittest.cc
-index 9aced70287c3ac877310457c1aad3b2544a85800..35f435d3d4d5eda44b69e5e66ec9480534d3ef44 100644
---- a/ui/views/widget/widget_unittest.cc
-+++ b/ui/views/widget/widget_unittest.cc
-@@ -1317,6 +1317,10 @@ TEST_P(WidgetWithDestroyedNativeViewOrNativeWidgetTest, Deactivate) {
-   widget()->Deactivate();
- }
- 
-+TEST_P(WidgetWithDestroyedNativeViewOrNativeWidgetTest, DebugToggleFrameType) {
-+  widget()->DebugToggleFrameType();
-+}
-+
- TEST_P(WidgetWithDestroyedNativeViewOrNativeWidgetTest, DraggedView) {
-   widget()->dragged_view();
- }
-diff --git a/ui/views/win/hwnd_message_handler.cc b/ui/views/win/hwnd_message_handler.cc
-index 575877b4fb0929d0cdd22af399f7078fcd713584..90dd6487fdf438a61672a81f08b545742045944a 100644
---- a/ui/views/win/hwnd_message_handler.cc
-+++ b/ui/views/win/hwnd_message_handler.cc
-@@ -1741,6 +1741,20 @@ void HWNDMessageHandler::ResetWindowRegion(bool force, bool redraw) {
-   }
- }
- 
-+void HWNDMessageHandler::UpdateDwmNcRenderingPolicy() {
-+  if (IsFullscreen())
-+    return;
-+
-+  DWMNCRENDERINGPOLICY policy =
-+      custom_window_region_.is_valid() ||
-+              delegate_->GetFrameMode() == FrameMode::CUSTOM_DRAWN
-+          ? DWMNCRP_DISABLED
-+          : DWMNCRP_ENABLED;
-+
-+  DwmSetWindowAttribute(hwnd(), DWMWA_NCRENDERING_POLICY, &policy,
-+                        sizeof(DWMNCRENDERINGPOLICY));
-+}
-+
- LRESULT HWNDMessageHandler::DefWindowProcWithRedrawLock(UINT message,
-                                                         WPARAM w_param,
-                                                         LPARAM l_param) {
-@@ -3607,10 +3621,34 @@ bool HWNDMessageHandler::IsSynthesizedMouseMessage(unsigned int message,
- }
- 
- void HWNDMessageHandler::PerformDwmTransition() {
--  CHECK(IsFrameSystemDrawn());
--
-   dwm_transition_desired_ = false;
-+
-+  UpdateDwmNcRenderingPolicy();
-+  // Don't redraw the window here, because we need to hide and show the window
-+  // which will also trigger a redraw.
-+  ResetWindowRegion(true, false);
-+  // The non-client view needs to update too.
-   delegate_->HandleFrameChanged();
-+  // This calls DwmExtendFrameIntoClientArea which must be called when DWM
-+  // composition state changes.
-+  UpdateDwmFrame();
-+
-+  if (IsVisible() && IsFrameSystemDrawn()) {
-+    // For some reason, we need to hide the window after we change from a custom
-+    // frame to a native frame.  If we don't, the client area will be filled
-+    // with black.  This seems to be related to an interaction between DWM and
-+    // SetWindowRgn, but the details aren't clear. Additionally, we need to
-+    // specify SWP_NOZORDER here, otherwise if you have multiple chrome windows
-+    // open they will re-appear with a non-deterministic Z-order.
-+    // Note: caused http://crbug.com/895855, where a laptop lid close+reopen
-+    // puts window in the background but acts like a foreground window. Fixed by
-+    // not calling this unless DWM composition actually changes. Finally, since
-+    // we don't want windows stealing focus if they're not already active, we
-+    // set SWP_NOACTIVATE.
-+    UINT flags = SWP_NOMOVE | SWP_NOSIZE | SWP_NOZORDER | SWP_NOACTIVATE;
-+    SetWindowPos(hwnd(), nullptr, 0, 0, 0, 0, flags | SWP_HIDEWINDOW);
-+    SetWindowPos(hwnd(), nullptr, 0, 0, 0, 0, flags | SWP_SHOWWINDOW);
-+  }
- }
- 
- void HWNDMessageHandler::UpdateDwmFrame() {
-diff --git a/ui/views/win/hwnd_message_handler.h b/ui/views/win/hwnd_message_handler.h
-index 7238af3f51179145a1c1eb9639ca756c2a697554..694945c4f3a62ed13a3b80cc5fba5673e29eef4e 100644
---- a/ui/views/win/hwnd_message_handler.h
-+++ b/ui/views/win/hwnd_message_handler.h
-@@ -324,6 +324,11 @@ class VIEWS_EXPORT HWNDMessageHandler : public gfx::WindowImpl,
-   // frame windows.
-   void ResetWindowRegion(bool force, bool redraw);
- 
-+  // Enables or disables rendering of the non-client (glass) area by DWM,
-+  // under Vista and above, depending on whether the caller has requested a
-+  // custom frame.
-+  void UpdateDwmNcRenderingPolicy();
-+
-   // Calls DefWindowProc, safely wrapping the call in a ScopedRedrawLock to
-   // prevent frame flicker. DefWindowProc handling can otherwise render the
-   // classic-look window title bar directly.
diff --git a/shell/browser/native_window.cc b/shell/browser/native_window.cc
index d33973ae9c..1c6a6b0bc7 100644
--- a/shell/browser/native_window.cc
+++ b/shell/browser/native_window.cc
@@ -316,47 +316,65 @@ bool NativeWindow::IsNormal() {
 
 void NativeWindow::SetSizeConstraints(
     const extensions::SizeConstraints& window_constraints) {
-  extensions::SizeConstraints content_constraints(GetContentSizeConstraints());
-  if (window_constraints.HasMaximumSize()) {
-    gfx::Rect max_bounds = WindowBoundsToContentBounds(
-        gfx::Rect(window_constraints.GetMaximumSize()));
-    content_constraints.set_maximum_size(max_bounds.size());
-  }
-  if (window_constraints.HasMinimumSize()) {
-    gfx::Rect min_bounds = WindowBoundsToContentBounds(
-        gfx::Rect(window_constraints.GetMinimumSize()));
-    content_constraints.set_minimum_size(min_bounds.size());
-  }
-  SetContentSizeConstraints(content_constraints);
+  size_constraints_ = window_constraints;
+  content_size_constraints_.reset();
 }
 
 extensions::SizeConstraints NativeWindow::GetSizeConstraints() const {
-  extensions::SizeConstraints content_constraints = GetContentSizeConstraints();
-  extensions::SizeConstraints window_constraints;
-  if (content_constraints.HasMaximumSize()) {
+  if (size_constraints_)
+    return *size_constraints_;
+  if (!content_size_constraints_)
+    return extensions::SizeConstraints();
+  // Convert content size constraints to window size constraints.
+  extensions::SizeConstraints constraints;
+  if (content_size_constraints_->HasMaximumSize()) {
     gfx::Rect max_bounds = ContentBoundsToWindowBounds(
-        gfx::Rect(content_constraints.GetMaximumSize()));
-    window_constraints.set_maximum_size(max_bounds.size());
+        gfx::Rect(content_size_constraints_->GetMaximumSize()));
+    constraints.set_maximum_size(max_bounds.size());
   }
-  if (content_constraints.HasMinimumSize()) {
+  if (content_size_constraints_->HasMinimumSize()) {
     gfx::Rect min_bounds = ContentBoundsToWindowBounds(
-        gfx::Rect(content_constraints.GetMinimumSize()));
-    window_constraints.set_minimum_size(min_bounds.size());
+        gfx::Rect(content_size_constraints_->GetMinimumSize()));
+    constraints.set_minimum_size(min_bounds.size());
   }
-  return window_constraints;
+  return constraints;
 }
 
 void NativeWindow::SetContentSizeConstraints(
     const extensions::SizeConstraints& size_constraints) {
-  size_constraints_ = size_constraints;
+  content_size_constraints_ = size_constraints;
+  size_constraints_.reset();
 }
 
+// The return value of GetContentSizeConstraints will be passed to Chromium
+// to set min/max sizes of window. Note that we are returning content size
+// instead of window size because that is what Chromium expects, see the
+// comment of |WidgetSizeIsClientSize| in Chromium's codebase to learn more.
 extensions::SizeConstraints NativeWindow::GetContentSizeConstraints() const {
-  return size_constraints_;
+  if (content_size_constraints_)
+    return *content_size_constraints_;
+  if (!size_constraints_)
+    return extensions::SizeConstraints();
+  // Convert window size constraints to content size constraints.
+  // Note that we are not caching the results, because Chromium reccalculates
+  // window frame size everytime when min/max sizes are passed, and we must
+  // do the same otherwise the resulting size with frame included will be wrong.
+  extensions::SizeConstraints constraints;
+  if (size_constraints_->HasMaximumSize()) {
+    gfx::Rect max_bounds = WindowBoundsToContentBounds(
+        gfx::Rect(size_constraints_->GetMaximumSize()));
+    constraints.set_maximum_size(max_bounds.size());
+  }
+  if (size_constraints_->HasMinimumSize()) {
+    gfx::Rect min_bounds = WindowBoundsToContentBounds(
+        gfx::Rect(size_constraints_->GetMinimumSize()));
+    constraints.set_minimum_size(min_bounds.size());
+  }
+  return constraints;
 }
 
 void NativeWindow::SetMinimumSize(const gfx::Size& size) {
-  extensions::SizeConstraints size_constraints;
+  extensions::SizeConstraints size_constraints = GetSizeConstraints();
   size_constraints.set_minimum_size(size);
   SetSizeConstraints(size_constraints);
 }
@@ -366,7 +384,7 @@ gfx::Size NativeWindow::GetMinimumSize() const {
 }
 
 void NativeWindow::SetMaximumSize(const gfx::Size& size) {
-  extensions::SizeConstraints size_constraints;
+  extensions::SizeConstraints size_constraints = GetSizeConstraints();
   size_constraints.set_maximum_size(size);
   SetSizeConstraints(size_constraints);
 }
diff --git a/shell/browser/native_window.h b/shell/browser/native_window.h
index 2394be0016..fcdf419d7e 100644
--- a/shell/browser/native_window.h
+++ b/shell/browser/native_window.h
@@ -423,6 +423,13 @@ class NativeWindow : public base::SupportsUserData,
   // The "titleBarStyle" option.
   TitleBarStyle title_bar_style_ = TitleBarStyle::kNormal;
 
+  // Minimum and maximum size.
+  absl::optional<extensions::SizeConstraints> size_constraints_;
+  // Same as above but stored as content size, we are storing 2 types of size
+  // constraints beacause converting between them will cause rounding errors
+  // on HiDPI displays on some environments.
+  absl::optional<extensions::SizeConstraints> content_size_constraints_;
+
   std::queue<bool> pending_transitions_;
   FullScreenTransitionState fullscreen_transition_state_ =
       FullScreenTransitionState::kNone;
@@ -450,9 +457,6 @@ class NativeWindow : public base::SupportsUserData,
   // Whether window is transparent.
   bool transparent_ = false;
 
-  // Minimum and maximum size, stored as content size.
-  extensions::SizeConstraints size_constraints_;
-
   // Whether window can be resized larger than screen.
   bool enable_larger_than_screen_ = false;
 
diff --git a/shell/browser/native_window_views.cc b/shell/browser/native_window_views.cc
index a1581d98d0..028b35c1ce 100644
--- a/shell/browser/native_window_views.cc
+++ b/shell/browser/native_window_views.cc
@@ -78,6 +78,7 @@
 #include "ui/display/screen.h"
 #include "ui/display/win/screen_win.h"
 #include "ui/gfx/color_utils.h"
+#include "ui/gfx/win/msg_util.h"
 #endif
 
 namespace electron {
@@ -138,6 +139,25 @@ gfx::Rect DIPToScreenRect(HWND hwnd, const gfx::Rect& pixel_bounds) {
   return screen_rect;
 }
 
+// Chromium uses a buggy implementation that converts content rect to window
+// rect when calculating min/max size, we should use the same implementation
+// when passing min/max size so we can get correct results.
+gfx::Size WindowSizeToContentSizeBuggy(HWND hwnd, const gfx::Size& size) {
+  // Calculate the size of window frame, using same code with the
+  // HWNDMessageHandler::OnGetMinMaxInfo method.
+  // The pitfall is, when window is minimized the calculated window frame size
+  // will be different from other states.
+  RECT client_rect, rect;
+  GetClientRect(hwnd, &client_rect);
+  GetWindowRect(hwnd, &rect);
+  CR_DEFLATE_RECT(&rect, &client_rect);
+  // Convert DIP size to pixel size, do calculation and then return DIP size.
+  gfx::Rect screen_rect = DIPToScreenRect(hwnd, gfx::Rect(size));
+  gfx::Size screen_client_size(screen_rect.width() - (rect.right - rect.left),
+                               screen_rect.height() - (rect.bottom - rect.top));
+  return ScreenToDIPRect(hwnd, gfx::Rect(screen_client_size)).size();
+}
+
 #endif
 
 #if defined(USE_OZONE)
@@ -812,6 +832,29 @@ void NativeWindowViews::SetContentSizeConstraints(
     old_size_constraints_ = size_constraints;
 }
 
+#if BUILDFLAG(IS_WIN)
+// This override does almost the same with its parent, except that it uses
+// the WindowSizeToContentSizeBuggy method to convert window size to content
+// size. See the comment of the method for the reason behind this.
+extensions::SizeConstraints NativeWindowViews::GetContentSizeConstraints()
+    const {
+  if (content_size_constraints_)
+    return *content_size_constraints_;
+  if (!size_constraints_)
+    return extensions::SizeConstraints();
+  extensions::SizeConstraints constraints;
+  if (size_constraints_->HasMaximumSize()) {
+    constraints.set_maximum_size(WindowSizeToContentSizeBuggy(
+        GetAcceleratedWidget(), size_constraints_->GetMaximumSize()));
+  }
+  if (size_constraints_->HasMinimumSize()) {
+    constraints.set_minimum_size(WindowSizeToContentSizeBuggy(
+        GetAcceleratedWidget(), size_constraints_->GetMinimumSize()));
+  }
+  return constraints;
+}
+#endif
+
 void NativeWindowViews::SetResizable(bool resizable) {
   if (resizable != resizable_) {
     // On Linux there is no "resizable" property of a window, we have to set
diff --git a/shell/browser/native_window_views.h b/shell/browser/native_window_views.h
index 8a2bf583bd..e97d22ace0 100644
--- a/shell/browser/native_window_views.h
+++ b/shell/browser/native_window_views.h
@@ -78,6 +78,9 @@ class NativeWindowViews : public NativeWindow,
   SkColor GetBackgroundColor() override;
   void SetContentSizeConstraints(
       const extensions::SizeConstraints& size_constraints) override;
+#if BUILDFLAG(IS_WIN)
+  extensions::SizeConstraints GetContentSizeConstraints() const override;
+#endif
   void SetResizable(bool resizable) override;
   bool MoveAbove(const std::string& sourceId) override;
   void MoveTop() override;