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 1e4d539b..b8a05abb 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
@@ -1699,12 +1699,6 @@
         [tc-e/t (inst (ann (lambda (a) a) (All (a) (a -> a))) Symbol)
                 (t:-> -Symbol -Symbol)]
         )
-  (test-suite
-   "check-type tests"
-   (test-exn "Fails correctly" exn:fail:syntax? (lambda () (parameterize ([orig-module-stx #'here])
-                                                             (check-type #'here N B))))
-   (test-not-exn "Doesn't fail on subtypes" (lambda () (check-type #'here N Univ)))
-   (test-not-exn "Doesn't fail on equal types" (lambda () (check-type #'here N N))))
   (test-suite
    "tc-literal tests"
    (tc-l 5 -PosByte)
diff --git a/pkgs/typed-racket-pkgs/typed-racket-tests/tests/typed-racket/fail/multiple-annotations-define.rkt b/pkgs/typed-racket-pkgs/typed-racket-tests/tests/typed-racket/fail/multiple-annotations-define.rkt
new file mode 100644
index 00000000..5e6b1180
--- /dev/null
+++ b/pkgs/typed-racket-pkgs/typed-racket-tests/tests/typed-racket/fail/multiple-annotations-define.rkt
@@ -0,0 +1,8 @@
+#;
+(exn-pred 1 "Body had type:.*Variable had type:.*")
+#lang typed/racket
+
+
+(: a Integer)
+(: b String)
+(define-values (a b c) (values 1 2 3))