diff --git a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/private/type-contract.rkt b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/private/type-contract.rkt
index 4001b3db..fcbd9811 100644
--- a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/private/type-contract.rkt
+++ b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/private/type-contract.rkt
@@ -148,7 +148,9 @@
         (loop t 'both structs-seen kind))
       (define (t->c/fun f #:method [method? #f])
         (match f
-          [(Function: (list (top-arr:))) #'(case->)]
+          [(Function: (list (top-arr:)))
+           (set-chaperone!)
+           #'(case->)]
           [(Function: arrs)
            (set-chaperone!)
            ;; Try to generate a single `->*' contract if possible.
diff --git a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/fail/pr13746.rkt b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/fail/pr13746.rkt
new file mode 100644
index 00000000..d03778a5
--- /dev/null
+++ b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/fail/pr13746.rkt
@@ -0,0 +1,6 @@
+#;
+(exn:pred #rx"Procedure could not be converted to a predicate")
+#lang typed/racket
+
+(define-predicate A? Procedure)
+