diff --git base/message_loop/message_pump_win.cc base/message_loop/message_pump_win.cc
index 908f0cdf45682781160b9937f015aa9af628b451..fe5a8000171bd3eecf12aab1b290e0c26cc25777 100644
--- base/message_loop/message_pump_win.cc
+++ base/message_loop/message_pump_win.cc
@@ -25,6 +25,7 @@
 #include "base/message_loop/message_pump_wakeup_counter.h"
 #include "base/numerics/safe_conversions.h"
 #include "base/strings/string_number_conversions.h"
+#include "base/task/current_thread.h"
 #include "base/task/task_features.h"
 #include "base/trace_event/interned_args_helper.h"
 #include "base/trace_event/typed_macros.h"
@@ -590,7 +591,19 @@ bool MessagePumpForUI::ProcessNextWindowsMessage() {
       if (native_event_observer_) {
         native_event_observer_->WillRunNativeEvent(next_peek_message_event_id_);
       }
-      has_msg = ::PeekMessage(&msg, nullptr, 0, 0, PM_REMOVE) != FALSE;
+
+      // We should not process all window messages if we are in the context of
+      // an OS modal loop, i.e. in the context of a windows API call like
+      // MessageBox. This is to ensure that these messages are peeked out by the
+      // OS modal loop.
+      if (CurrentThread::Get()->os_modal_loop()) {
+        // We only peek out WM_PAINT and WM_TIMER here for reasons mentioned
+        // above.
+        has_msg = PeekMessage(&msg, NULL, WM_PAINT, WM_PAINT, PM_REMOVE) ||
+                  PeekMessage(&msg, NULL, WM_TIMER, WM_TIMER, PM_REMOVE);
+      } else {
+        has_msg = PeekMessage(&msg, NULL, 0, 0, PM_REMOVE) != FALSE;
+      }
       if (native_event_observer_) {
         native_event_observer_->DidRunNativeEvent(
             next_peek_message_event_id_++);
diff --git base/task/current_thread.cc base/task/current_thread.cc
index dd959f737c8c66d6370d45a392a90e9abbbe5f0f..d257d16cb1ba1787662c119270715d6f7da7dc38 100644
--- base/task/current_thread.cc
+++ base/task/current_thread.cc
@@ -51,6 +51,8 @@ void CurrentThread::AddDestructionObserver(
 
 void CurrentThread::RemoveDestructionObserver(
     DestructionObserver* destruction_observer) {
+  if (!current_)
+    return;
   DCHECK(current_->IsBoundToCurrentThread());
   current_->RemoveDestructionObserver(destruction_observer);
 }
diff --git base/task/current_thread.h base/task/current_thread.h
index 2bf2f919fe5cba57049cb7e80a92603c8d4980b8..72bde82f6b62e3981029d7c9ca876c853b563298 100644
--- base/task/current_thread.h
+++ base/task/current_thread.h
@@ -160,6 +160,12 @@ class BASE_EXPORT CurrentThread {
       RegisterOnNextIdleCallbackPasskey,
       OnceClosure on_next_idle_callback);
 
+#if BUILDFLAG(IS_WIN)
+  void set_os_modal_loop(bool os_modal_loop) { os_modal_loop_ = os_modal_loop; }
+
+  bool os_modal_loop() const { return os_modal_loop_; }
+#endif  // OS_WIN
+
   // Enables nested task processing in scope of an upcoming native message loop.
   // Some unwanted message loops may occur when using common controls or printer
   // functions. Hence, nested task processing is disabled by default to avoid
@@ -233,6 +239,13 @@ class BASE_EXPORT CurrentThread {
   friend class web::WebTaskEnvironment;
 
   raw_ptr<sequence_manager::internal::SequenceManagerImpl> current_;
+
+#if BUILDFLAG(IS_WIN)
+ private:
+  // Should be set to true before calling Windows APIs like TrackPopupMenu, etc.
+  // which enter a modal message loop.
+  bool os_modal_loop_ = false;
+#endif
 };
 
 // UI extension of CurrentThread.