diff --git a/pkgs/racket-test-core/tests/racket/chaperone.rktl b/pkgs/racket-test-core/tests/racket/chaperone.rktl
index 36b07e7624..a865483963 100644
--- a/pkgs/racket-test-core/tests/racket/chaperone.rktl
+++ b/pkgs/racket-test-core/tests/racket/chaperone.rktl
@@ -1729,7 +1729,10 @@
 
     (test #t blue? (make-a (chaperone-struct a1 struct:a prop:blue 'color) 2))
     (test 'color blue-ref (make-a (chaperone-struct a1 struct:a prop:blue 'color) 2))
-    
+
+    (test #f blue? a1)
+    (err/rt-test (blue-ref a1))
+
     (void)))
 
 ;; ----------------------------------------
diff --git a/racket/src/racket/src/struct.c b/racket/src/racket/src/struct.c
index fed91ba2c4..dcb5deba9b 100644
--- a/racket/src/racket/src/struct.c
+++ b/racket/src/racket/src/struct.c
@@ -1022,9 +1022,11 @@ static Scheme_Object *prop_pred(int argc, Scheme_Object **args, Scheme_Object *p
          be via `prop:impersonator-of`: */
       Scheme_Object *procs;
       procs = scheme_struct_type_property_ref(scheme_impersonator_of_property, v);
-      if (procs)
+      if (procs) {
         v = scheme_apply_impersonator_of(0, procs, v);
-      else
+        if (!v)
+          return scheme_false;
+      } else
         return scheme_false;
     } else
       break;
@@ -1179,6 +1181,8 @@ static Scheme_Object *do_chaperone_prop_accessor(const char *who, Scheme_Object
         procs = scheme_struct_type_property_ref(scheme_impersonator_of_property, arg);
         if (procs) {
           arg = scheme_apply_impersonator_of(0, procs, arg);
+          if (!arg)
+            return NULL;
           /* loop to try again */
         } else {
           /* an impersonator property lives at the impersonator/chaperone level, only: */