diff --git a/shell/browser/native_window_mac.mm b/shell/browser/native_window_mac.mm
index 2acea0428068..6889eb6f1873 100644
--- a/shell/browser/native_window_mac.mm
+++ b/shell/browser/native_window_mac.mm
@@ -429,7 +429,13 @@ void NativeWindowMac::ShowInactive() {
   if (parent())
     InternalSetParentWindow(parent(), true);
 
+  // Triggers `NativeWidgetMacNSWindowHost::OnVisibilityChanged`.
+  widget()->ShowInactive();
+  // `Widget::ShowInactive` is not sufficient to bring window to front.
   [window_ orderFrontRegardless];
+  // Above calls do not trigger `orderWindow: relativeTo:` in which headless
+  // mode is being disabled.
+  [window_ disableHeadlessMode];
 }
 
 void NativeWindowMac::Hide() {
diff --git a/shell/browser/ui/cocoa/electron_ns_window.h b/shell/browser/ui/cocoa/electron_ns_window.h
index 63ea5355467d..8c026c0b0bdc 100644
--- a/shell/browser/ui/cocoa/electron_ns_window.h
+++ b/shell/browser/ui/cocoa/electron_ns_window.h
@@ -49,6 +49,7 @@ class ElectronNativeWindowObserver;
 - (NSRect)originalContentRectForFrameRect:(NSRect)frameRect;
 - (BOOL)toggleFullScreenMode:(id)sender;
 - (NSImage*)_cornerMask;
+- (void)disableHeadlessMode;
 @end
 
 #endif  // ELECTRON_SHELL_BROWSER_UI_COCOA_ELECTRON_NS_WINDOW_H_
diff --git a/shell/browser/ui/cocoa/electron_ns_window.mm b/shell/browser/ui/cocoa/electron_ns_window.mm
index 30780277d3a5..6555f47f5bc3 100644
--- a/shell/browser/ui/cocoa/electron_ns_window.mm
+++ b/shell/browser/ui/cocoa/electron_ns_window.mm
@@ -259,13 +259,7 @@ void SwizzleSwipeWithEvent(NSView* view, SEL swiz_selector) {
 }
 
 - (void)orderWindow:(NSWindowOrderingMode)place relativeTo:(NSInteger)otherWin {
-  if (shell_) {
-    // We initialize the window in headless mode to allow painting before it is
-    // shown, but we don't want the headless behavior of allowing the window to
-    // be placed unconstrained.
-    self.isHeadless = false;
-    shell_->widget()->DisableHeadlessMode();
-  }
+  [self disableHeadlessMode];
   [super orderWindow:place relativeTo:otherWin];
 }
 
@@ -328,6 +322,16 @@ void SwizzleSwipeWithEvent(NSView* view, SEL swiz_selector) {
   }
 }
 
+- (void)disableHeadlessMode {
+  if (shell_) {
+    // We initialize the window in headless mode to allow painting before it is
+    // shown, but we don't want the headless behavior of allowing the window to
+    // be placed unconstrained.
+    self.isHeadless = false;
+    shell_->widget()->DisableHeadlessMode();
+  }
+}
+
 // Quicklook methods
 
 - (BOOL)acceptsPreviewPanelControl:(QLPreviewPanel*)panel {