diff --git a/src/msw/menuitem.cpp b/src/msw/menuitem.cpp
index 65ffdb6a16..a6593f35ed 100644
--- a/src/msw/menuitem.cpp
+++ b/src/msw/menuitem.cpp
@@ -1352,7 +1352,8 @@ bool wxMenuItem::MSWMustUseOwnerDrawn()
                                 GetFont().IsOk();
 
     // Windows XP or earlier don't display menu bitmaps bigger than
-    // standard size correctly (they're truncated), so we must use
+    // standard size correctly (they're truncated) nor can
+    // checked bitmaps use HBMMENU_CALLBACK, so we must use
     // owner-drawn items to show them correctly there. OTOH Win7
     // doesn't seem to have any problems with even very large bitmaps
     // so don't use owner-drawn items unnecessarily there (Vista wasn't
@@ -1363,7 +1364,8 @@ bool wxMenuItem::MSWMustUseOwnerDrawn()
                         bmpChecked   = GetBitmap(true);
 
         if ( (bmpUnchecked.IsOk() && IsGreaterThanStdSize(bmpUnchecked)) ||
-                (bmpChecked.IsOk()   && IsGreaterThanStdSize(bmpChecked)) )
+                (bmpChecked.IsOk()   && IsGreaterThanStdSize(bmpChecked)) ||
+                (bmpChecked.IsOk() && IsCheckable()) )
         {
             mustUseOwnerDrawn = true;
         }