diff --git base/message_loop/message_loop_current.h base/message_loop/message_loop_current.h
index 72b0d8c6fe8c..f5df6369f269 100644
--- base/message_loop/message_loop_current.h
+++ base/message_loop/message_loop_current.h
@@ -126,6 +126,16 @@ class BASE_EXPORT MessageLoopCurrent {
   void AddTaskObserver(TaskObserver* task_observer);
   void RemoveTaskObserver(TaskObserver* task_observer);
 
+#if defined(OS_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 or disables the recursive task processing. This happens in the case
   // of recursive message loops. Some unwanted message loops may occur when
   // using common controls or printer functions. By default, recursive task
@@ -199,6 +209,13 @@ class BASE_EXPORT MessageLoopCurrent {
   explicit MessageLoopCurrent(MessageLoop* current) : current_(current) {}
 
   MessageLoop* const current_;
+
+#if defined(OS_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
 };
 
 #if !defined(OS_NACL)
diff --git base/message_loop/message_pump_win.cc base/message_loop/message_pump_win.cc
index ca257370fb56..3d9b4cea21ce 100644
--- base/message_loop/message_pump_win.cc
+++ base/message_loop/message_pump_win.cc
@@ -370,20 +370,28 @@ bool MessagePumpForUI::ProcessMessageHelper(const MSG& msg) {
 }
 
 bool MessagePumpForUI::ProcessPumpReplacementMessage() {
-  // When we encounter a kMsgHaveWork message, this method is called to peek and
-  // process a replacement message. The goal is to make the kMsgHaveWork as non-
-  // intrusive as possible, even though a continuous stream of such messages are
-  // posted. This method carefully peeks a message while there is no chance for
-  // a kMsgHaveWork to be pending, then resets the |have_work_| flag (allowing a
-  // replacement kMsgHaveWork to possibly be posted), and finally dispatches
-  // that peeked replacement. Note that the re-post of kMsgHaveWork may be
-  // asynchronous to this thread!!
-
+  // When we encounter a kMsgHaveWork message, this method is called to peek
+  // and process a replacement message, such as a WM_PAINT or WM_TIMER.  The
+  // goal is to make the kMsgHaveWork as non-intrusive as possible, even though
+  // a continuous stream of such messages are posted.  This method carefully
+  // peeks a message while there is no chance for a kMsgHaveWork to be pending,
+  // then resets the have_work_ flag (allowing a replacement kMsgHaveWork to
+  // possibly be posted), and finally dispatches that peeked replacement.  Note
+  // that the re-post of kMsgHaveWork may be asynchronous to this thread!!
+
+  bool have_message = false;
   MSG msg;
-  const bool have_message =
-      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 (MessageLoop::current()->os_modal_loop()) {
+    // We only peek out WM_PAINT and WM_TIMER here for reasons mentioned above.
+    have_message = PeekMessage(&msg, NULL, WM_PAINT, WM_PAINT, PM_REMOVE) ||
+                   PeekMessage(&msg, NULL, WM_TIMER, WM_TIMER, PM_REMOVE);
+  } else {
+    have_message = PeekMessage(&msg, NULL, 0, 0, PM_REMOVE) != FALSE;
+  }
 
-  // Expect no message or a message different than kMsgHaveWork.
   DCHECK(!have_message || kMsgHaveWork != msg.message ||
          msg.hwnd != message_window_.hwnd());