diff --git a/pkgs/racket-pkgs/racket-test/tests/racket/chaperone.rktl b/pkgs/racket-pkgs/racket-test/tests/racket/chaperone.rktl
index eaa7fb5545..de9523ed4f 100644
--- a/pkgs/racket-pkgs/racket-test/tests/racket/chaperone.rktl
+++ b/pkgs/racket-pkgs/racket-test/tests/racket/chaperone.rktl
@@ -253,18 +253,24 @@
 (err/rt-test ((chaperone-procedure (lambda (x) x) (lambda (y) (values (lambda (z) 89) y))) 10))
 
 (test 88 (impersonate-procedure* (lambda (x) x) (lambda (self y) 88)) 10)
-(letrec ([final (impersonate-procedure*
-                 (impersonate-procedure
-                  (impersonate-procedure* (lambda (x) x)
-                                          (lambda (self y)
-                                            (test #t eq? self final)
-                                            (add1 y)))
-                  (lambda (y)
-                    (add1 y)))
-                 (lambda (self y)
-                   (test #t eq? self final)
-                   (add1 y)))])
-  (test 13 final 10))
+(let-values ([(prop:blue blue? blue-ref) (make-impersonator-property 'blue)])
+  (letrec ([final (impersonate-procedure*
+                   (impersonate-procedure
+                    (impersonate-procedure
+                     (impersonate-procedure* (lambda (x) x)
+                                             (lambda (self y)
+                                               (test #t eq? self final)
+                                               (test 'whale blue-ref self)
+                                               (add1 y)))
+                     (lambda (y)
+                       (add1 y)))
+                    #f
+                    prop:blue
+                    'whale)
+                   (lambda (self y)
+                     (test #t eq? self final)
+                     (add1 y)))])
+    (test 13 final 10)))
 (letrec ([final (impersonate-procedure*
                  (impersonate-procedure
                   (impersonate-procedure* (lambda (x) x)
diff --git a/racket/src/racket/src/fun.c b/racket/src/racket/src/fun.c
index a9dfeb0a79..eecef56507 100644
--- a/racket/src/racket/src/fun.c
+++ b/racket/src/racket/src/fun.c
@@ -3627,6 +3627,10 @@ Scheme_Object *scheme_apply_chaperone(Scheme_Object *o, int argc, Scheme_Object
 
   if (SCHEME_FALSEP(SCHEME_VEC_ELS(px->redirects)[0])) {
     /* no redirection procedure */
+    if (SCHEME_CHAPERONEP(px->prev)) {
+      /* commuincate `self_proc` to the next layer: */
+      scheme_current_thread->self_for_proc_chaperone = self_proc;
+    }
     return _scheme_tail_apply(px->prev, argc, argv);
   }