diff --git a/typed-racket-test/succeed/issue-33.rkt b/typed-racket-test/succeed/issue-33.rkt
new file mode 100644
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+++ b/typed-racket-test/succeed/issue-33.rkt
@@ -0,0 +1,17 @@
+#lang typed/racket/base
+
+;; regression test for issue #33
+;; https://github.com/racket/typed-racket/issues/33
+
+;; In 2015, gave the error message:
+;;   Type Checker: type mismatch
+;;    expected: (U (List Symbol Any) (List String Symbol))
+;;    given: (List String Any)
+;;    in: (list "foo" (quote bold))
+
+(: x (U (List Symbol Any)
+        (List String Symbol)))
+(define x (list "foo" 'bold))
+
+(when (and (string? (car x)) (symbol? (cadr x)))
+  (ann x (List String Symbol)))