diff --git a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/utils/any-wrap.rkt b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/utils/any-wrap.rkt
index 8c60bc5a..d1951185 100644
--- a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/utils/any-wrap.rkt
+++ b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/utils/any-wrap.rkt
@@ -99,10 +99,7 @@
       ;; chaperones, or if i could tell if they were immutable.
       [(? struct?) (wrap-struct neg-party v)]
       [(? procedure?)
-       (if (procedure-arity-includes? v 0)
-           (chaperone-procedure v (case-lambda [() (values)]
-                                               [_ (fail neg-party v)]))
-           (chaperone-procedure v (lambda args (fail neg-party v))))]
+       (chaperone-procedure v (lambda args (fail neg-party v)))]
       [(? promise?)
        (chaperone-struct
         v
diff --git a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/fail/pr14173.rkt b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/fail/pr14173.rkt
new file mode 100644
index 00000000..6c69b9fd
--- /dev/null
+++ b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/fail/pr14173.rkt
@@ -0,0 +1,13 @@
+#;
+(exn-pred "use a higher-order value")
+#lang racket
+
+(module t typed/racket #:no-optimize
+  (provide f g)
+
+  (define f (ann (case-lambda [() (add1 "hello")] [(x) x]) (Number -> Number)))
+  (define g (ann f Any)))
+
+(require 't)
+(f 1)
+(g)
\ No newline at end of file
diff --git a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/typecheck-tests.rkt b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/typecheck-tests.rkt
index 35346005..80b4f637 100644
--- a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/typecheck-tests.rkt
+++ b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/typecheck-tests.rkt
@@ -296,6 +296,7 @@
   ;; Needed for constructing TR types in expected values
   (for-syntax
     (rep type-rep filter-rep object-rep)
+    (base-env base-structs)
     (rename-in (types abbrev union numeric-tower filter-ops utils resolve)
                [Un t:Un]
                [-> t:->])))
@@ -3177,12 +3178,11 @@
         #:msg #rx"expected: Symbol.*given: Any"]
        
        [tc-err
-        (raise (λ ([x : Number]) (add1 x)))
-        #:ret (ret (Un))]
+        (raise (λ ([x : Number]) (add1 x)))]
        
        [tc-err
-        (exn:fail:syntax "" (current-continuation-marks) (list (datum->syntax #f add1)))
-        #:ret (ret -Exn)]
+        (raise (exn:fail:syntax "" (current-continuation-marks)
+                                (list (datum->syntax #f add1))))]
 
        ;; PR 14218
        [tc-e (ann (values "foo" "bar") (Values String String))