diff --git a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/fail/pr14144.rkt b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/fail/pr14144.rkt
new file mode 100644
index 0000000000..492389eb08
--- /dev/null
+++ b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/fail/pr14144.rkt
@@ -0,0 +1,13 @@
+#;
+(exn-pred #rx"Expected 'foo, but got 'bar")
+#lang racket/load
+
+;; Test for PR 14144
+;; Make sure that the second definition is checked
+;; against the synthesized type for the first definition
+
+(require typed/racket)
+
+(define x 'foo)
+(define x 'bar)
+