diff --git a/pkgs/racket-test-core/tests/racket/chaperone.rktl b/pkgs/racket-test-core/tests/racket/chaperone.rktl
index 7b1e6d5c90..b6bf1197f3 100644
--- a/pkgs/racket-test-core/tests/racket/chaperone.rktl
+++ b/pkgs/racket-test-core/tests/racket/chaperone.rktl
@@ -2123,6 +2123,38 @@
      (test #f chaperone-of? (hash-set h3 2 sub1) h3)))
  (list #hash() #hasheq() #hasheqv()))
 
+;; Make sure that multiple chaperone/impersonator layers
+;; are allowed by `chaperone-of?` and `impersonator-of?`
+(as-chaperone-or-impersonator
+ ([chaperone-hash impersonate-hash]
+  [chaperone-of? impersonator-of?])
+ (define ht (make-hash))
+
+ (define (chaperone ht)
+   (chaperone-hash
+    ht
+    (lambda (ht k) (values k (lambda (hc k v) v)))
+    (lambda (ht k v)
+      (values (chaperone-hash
+               k
+               (lambda (ht k) (values k (lambda (hc k v) v)))
+               (lambda (ht k v) (values k v))
+               (lambda (ht k) k)
+               (lambda (ht k) k))
+              v))
+    (lambda (ht k) k)
+    (lambda (ht k) k)))
+
+ (define ht0 (chaperone ht))
+ (define ht1 (chaperone ht0))
+
+ (test #t chaperone-of? ht1 ht)
+ (test #t chaperone-of? ht1 ht0)
+ (test #f chaperone-of? ht ht1)
+ (test #f chaperone-of? ht0 ht1)
+ (hash-set! ht1 (make-hash '((a . b))) 'ok)
+ (test 'ok hash-ref ht1 (make-hash '((a . b)))))
+
 ;; ----------------------------------------
 
 (as-chaperone-or-impersonator
diff --git a/racket/src/cs/rumble/equal.ss b/racket/src/cs/rumble/equal.ss
index 46c3905901..bd79b9c226 100644
--- a/racket/src/cs/rumble/equal.ss
+++ b/racket/src/cs/rumble/equal.ss
@@ -12,17 +12,19 @@
             ;; For immutable hashes, it's ok for the two objects to not be eq,
             ;; as long as the interpositions are the same and the underlying
             ;; values are `{impersonator,chaperone}-of?`:
-            (and (eq? (hash-impersonator-procs a)
-                      (hash-impersonator-procs b))
-                 (loop (impersonator-next a)
-                       (impersonator-next b)))]
+            (if (eq? (hash-impersonator-procs a)
+                     (hash-impersonator-procs b))
+                (loop (impersonator-next a)
+                      (impersonator-next b))
+                (loop (impersonator-next a) b))]
            [(and (hash-chaperone? a)
                  (hash-chaperone? b))
             ;; Same as above
-            (and (eq? (hash-chaperone-procs a)
-                      (hash-chaperone-procs b))
-                 (loop (impersonator-next a)
-                       (impersonator-next b)))]
+            (if (eq? (hash-chaperone-procs a)
+                     (hash-chaperone-procs b))
+                (loop (impersonator-next a)
+                      (impersonator-next b))
+                (loop (impersonator-next a) b))]
            [(and (props-impersonator? b)
                  (not (eq? mode 'chaperone-of?)))
             (loop a (impersonator-next b))]