diff --git a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/typecheck/tc-app-helper.rkt b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/typecheck/tc-app-helper.rkt
index f4334a48..7a2ae295 100644
--- a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/typecheck/tc-app-helper.rkt
+++ b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/typecheck/tc-app-helper.rkt
@@ -230,8 +230,9 @@
                              [(Values: (list (Result: t _ _)))
                               t]
                              [(ValuesDots: (list (Result: t _ _)) _ _)
-                              t])])
-                  (subtype rng expected-ty))]))))
+                              t]
+                             [_ #f])])
+                  (and rng (subtype rng expected-ty)))]))))
 
   (define orig (map list doms rngs rests drests))
 
diff --git a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/interactive-tests.rkt b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/interactive-tests.rkt
index ac749dba..e30068a3 100644
--- a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/interactive-tests.rkt
+++ b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/interactive-tests.rkt
@@ -168,4 +168,6 @@
     (test-form-exn #rx"exactly two arguments"
       (:query-type/result))
     (test-form-exn #rx"exactly two arguments"
-      (:query-type/result 1 2 3))))
+      (:query-type/result 1 2 3))
+    (test-form #rx"not in the given function's range"
+      (:query-type/result syntax-local-expand-expression Boolean))))
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 f516bee1..dcb10d30 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
@@ -3123,6 +3123,15 @@
           y)
         #:ret (ret -String -true-filter)
         #:msg #rx"expected: String.*given: (Null|'\\(\\))"]
+
+       ;; PR 14493
+       [tc-err
+        (let ()
+          (define f values)
+          (: g (Any -> Boolean))
+          (define (g x) (f x))
+          (error "foo"))
+        #:msg #rx"Polymorphic function `f' could not be applied"]
         )
 
   (test-suite