diff --git a/pkgs/racket-test-core/tests/racket/chaperone.rktl b/pkgs/racket-test-core/tests/racket/chaperone.rktl
index 5469faba30..782b3e2966 100644
--- a/pkgs/racket-test-core/tests/racket/chaperone.rktl
+++ b/pkgs/racket-test-core/tests/racket/chaperone.rktl
@@ -3005,6 +3005,50 @@
         ((wrap (lambda (x) (+ ((wrap (lambda (x) x)) x) 0))) 42))
   (test '(#f #f) values msgs))
 
+;; Make sure that `impersonator-prop:application-mark'
+;; works with keyword-based procedures:
+(let ()
+  (define (f x #:y y)
+    (call-with-immediate-continuation-mark
+     'z
+     (lambda (val)
+       (list val
+             (continuation-mark-set->list (current-continuation-marks) 'z)))))
+  (define g (chaperone-procedure
+             f
+             (lambda (a #:y y)
+               (values (lambda (r) r)
+                       (list y)
+                       a))
+             impersonator-prop:application-mark
+             (cons 'z 12)))
+  (test '(#f ()) 'kw-y-f (f 10 #:y 3))
+  (test '(12 (12)) 'kw-y-g (g 10 #:y 3))
+  (void))
+(let ()
+  (define (f x #:y [y 'no])
+    (call-with-immediate-continuation-mark
+     'z
+     (lambda (val)
+       (list val
+             (continuation-mark-set->list (current-continuation-marks) 'z)))))
+  (define g (chaperone-procedure
+             f
+             (lambda (a #:y [y 'no])
+               (if (eq? y 'no)
+                   (values (lambda (r) r)
+                           a)
+                   (values (lambda (r) r)
+                           (list y)
+                           a)))
+             impersonator-prop:application-mark
+             (cons 'z 12)))
+  (test '(#f ()) 'kw-no-y-f (f 10))
+  (test '(12 (12)) 'kw-no-y-g (g 10))
+  (test '(#f ()) 'kw-y-f (f 10 #:y 3))
+  (test '(12 (12)) 'kw-y-g (g 10 #:y 3))
+  (void))
+
 ;; ----------------------------------------
 
 ;; Check that supplying a procedure `to make-keyword-procedure' that 
diff --git a/racket/collects/racket/private/kw.rkt b/racket/collects/racket/private/kw.rkt
index 29825b2dd7..ba021aaff7 100644
--- a/racket/collects/racket/private/kw.rkt
+++ b/racket/collects/racket/private/kw.rkt
@@ -1882,7 +1882,18 @@
           (apply chaperone-procedure proc wrap-proc props)
           (begin
             (chaperone-arity-match-checking self-arg? name proc wrap-proc props)
-            (let*-values ([(kw-chaperone)
+            (let*-values ([(mark-prop) (let loop ([props props])
+                                         (cond
+                                           [(null? props) #f]
+                                           [(eq? (car props) impersonator-prop:application-mark)
+                                            (cadr props)]
+                                           [else (loop (cddr props))]))]
+                          [(chaperone-procedure/add-mark)
+                           (lambda (proc wrap-proc)
+                             (if mark-prop
+                                 (chaperone-procedure proc wrap-proc impersonator-prop:application-mark mark-prop)
+                                 (chaperone-procedure proc wrap-proc)))]
+                          [(kw-chaperone)
                            (let ([p (keyword-procedure-proc n-wrap-proc)])
                              ;; `extra-arg ...` will be `self-proc` if `self-arg?`:
                              (define-syntax gen-wrapper
@@ -1971,7 +1982,7 @@
                                          (if (okp? n-proc)
                                              ;; All keyword arguments are optional, so need to
                                              ;; chaperone as a plain procedure, too:
-                                             (chaperone-procedure proc wrap-proc)
+                                             (chaperone-procedure/add-mark proc wrap-proc)
                                              ;; Some keyword is required:
                                              proc)
                                          new-procedure-ref
@@ -2020,22 +2031,22 @@
                                          make-optional-keyword-method-impersonator
                                          make-optional-keyword-procedure-impersonator)
                                      (keyword-procedure-checker n-proc)
-                                     (chaperone-procedure (keyword-procedure-proc n-proc)
-                                                          kw-chaperone)
+                                     (chaperone-procedure/add-mark (keyword-procedure-proc n-proc)
+                                                                   kw-chaperone)
                                      (keyword-procedure-required n-proc)
                                      (keyword-procedure-allowed n-proc)
-                                     (chaperone-procedure (okp-ref n-proc 0)
-                                                          (okp-ref n-wrap-proc 0))
+                                     (chaperone-procedure/add-mark (okp-ref n-proc 0)
+                                                                   (okp-ref n-wrap-proc 0))
                                      n-proc)
                                     (chaperone-struct
                                      proc
                                      keyword-procedure-proc
                                      (lambda (self proc)
-                                       (chaperone-procedure proc kw-chaperone))
+                                       (chaperone-procedure/add-mark proc kw-chaperone))
                                      (make-struct-field-accessor okp-ref 0)
                                      (lambda (self proc)
-                                       (chaperone-procedure proc
-                                                            (okp-ref n-wrap-proc 0)))))
+                                       (chaperone-procedure/add-mark proc
+                                                                     (okp-ref n-wrap-proc 0)))))
                                 keyword-procedure-proc)]
                               [else
                                (values
@@ -2045,7 +2056,7 @@
                                            [mk (make-required (car name+fail) (cdr name+fail) (keyword-method? n-proc) #t)])
                                       (mk
                                        (keyword-procedure-checker n-proc)
-                                       (chaperone-procedure (keyword-procedure-proc n-proc) kw-chaperone)
+                                       (chaperone-procedure/add-mark (keyword-procedure-proc n-proc) kw-chaperone)
                                        (keyword-procedure-required n-proc)
                                        (keyword-procedure-allowed n-proc)
                                        n-proc))
@@ -2053,7 +2064,7 @@
                                      n-proc
                                      keyword-procedure-proc
                                      (lambda (self proc)
-                                       (chaperone-procedure proc kw-chaperone))))
+                                       (chaperone-procedure/add-mark proc kw-chaperone))))
                                 keyword-procedure-proc)]))])
               (if (null? props)
                   new-proc