diff --git a/src/msw/menu.cpp b/src/msw/menu.cpp
index 8a257768f9..3d3ea7e7b0 100644
--- a/src/msw/menu.cpp
+++ b/src/msw/menu.cpp
@@ -1367,10 +1367,6 @@ bool wxMenuBar::Insert(size_t pos, wxMenu *menu, const wxString& title)
         (GetHmenu() != 0);
 #endif
 
-    int mswpos = (!isAttached || (pos == m_menus.GetCount()))
-        ?   -1 // append the menu
-        :   MSWPositionForWxMenu(GetMenu(pos),pos);
-
     if ( !wxMenuBarBase::Insert(pos, menu, title) )
         return false;
 
@@ -1398,9 +1394,33 @@ bool wxMenuBar::Insert(size_t pos, wxMenu *menu, const wxString& title)
             wxLogLastError(wxT("TB_INSERTBUTTON"));
             return false;
         }
-        wxUnusedVar(mswpos);
 #else
-        if ( !::InsertMenu(GetHmenu(), mswpos,
+        // We have a problem with the index if there is an extra "Window" menu
+        // in this menu bar, which is added by wxMDIParentFrame to it directly
+        // using Windows API (so that it remains invisible to the user code),
+        // but which does affect the indices of the items we insert after it.
+        // So we check if any of the menus before the insertion position is a
+        // foreign one and adjust the insertion index accordingly.
+        int mswExtra = 0;
+
+        // Skip all this if the total number of menus matches (notice that the
+        // internal menu count has already been incremented by wxMenuBarBase::
+        // Insert() call above, hence -1).
+        int mswCount = ::GetMenuItemCount(GetHmenu());
+        if ( mswCount != -1 &&
+                static_cast<unsigned>(mswCount) != GetMenuCount() - 1 )
+        {
+            wxMenuList::compatibility_iterator node = m_menus.GetFirst();
+            for ( size_t n = 0; n < pos; n++ )
+            {
+                if ( ::GetSubMenu(GetHmenu(), n) != GetHmenuOf(node->GetData()) )
+                    mswExtra++;
+                else
+                    node = node->GetNext();
+            }
+        }
+
+        if ( !::InsertMenu(GetHmenu(), pos + mswExtra,
                            MF_BYPOSITION | MF_POPUP | MF_STRING,
                            (UINT_PTR)GetHmenuOf(menu), title.t_str()) )
         {