diff --git a/racket/src/racket/src/fun.c b/racket/src/racket/src/fun.c
index 7de6aba075..5053cb3115 100644
--- a/racket/src/racket/src/fun.c
+++ b/racket/src/racket/src/fun.c
@@ -3750,7 +3750,20 @@ Scheme_Object *scheme_apply_chaperone(Scheme_Object *o, int argc, Scheme_Object
       /* communicate `self_proc` to the next layer: */
       scheme_current_thread->self_for_proc_chaperone = self_proc;
     }
-    return _scheme_tail_apply(px->prev, argc, argv);
+    if (checks) {
+      /* cannot return a tail call */
+      MZ_CONT_MARK_POS -= 2;
+      if (checks & 0x1) {
+        v = _scheme_apply(px->prev, argc, argv);
+      } else if (SAME_TYPE(SCHEME_TYPE(px->prev), scheme_native_closure_type)) {
+        v = _apply_native(px->prev, argc, argv);
+      } else {
+        v = _scheme_apply_multi(px->prev, argc, argv);
+      }
+      MZ_CONT_MARK_POS += 2;
+      return v;
+    } else
+      return _scheme_tail_apply(px->prev, argc, argv);
   }
 
   /* Ensure that the original procedure accepts `argc' arguments: */
diff --git a/racket/src/racket/src/schnapp.inc b/racket/src/racket/src/schnapp.inc
index 31a4fc6d82..a3d585406d 100644
--- a/racket/src/racket/src/schnapp.inc
+++ b/racket/src/racket/src/schnapp.inc
@@ -62,8 +62,9 @@ Scheme_Object *PRIM_APPLY_NAME(Scheme_Object *rator,
 
     if (t == scheme_prim_type) {
       return PRIM_APPLY_NAME_FAST(rator, argc, argv);
-    } if ((t == scheme_proc_chaperone_type)
-          && SCHEME_MPAIRP(((Scheme_Chaperone *)rator)->redirects)) {
+    } else if ((t == scheme_proc_chaperone_type)
+               && SCHEME_VECTORP(((Scheme_Chaperone *)rator)->redirects)
+               && (SCHEME_VEC_SIZE(((Scheme_Chaperone *)rator)->redirects) & 0x1)) {
       return scheme_apply_chaperone(rator, argc, argv, NULL, PRIM_CHECK_MULTI | (PRIM_CHECK_VALUE << 1));
     }
   }