diff --git a/typed-racket-lib/typed-racket/typecheck/tc-app/tc-app-eq.rkt b/typed-racket-lib/typed-racket/typecheck/tc-app/tc-app-eq.rkt
index 03d67438..4f128ae3 100644
--- a/typed-racket-lib/typed-racket/typecheck/tc-app/tc-app-eq.rkt
+++ b/typed-racket-lib/typed-racket/typecheck/tc-app/tc-app-eq.rkt
@@ -57,8 +57,8 @@
       (tc-result1: (Value: (? ok? val2)) _ o2))
      (ret -Boolean (-FS (-and (-filter (-val val2) o1)
                               (-filter (-val val1) o2))
-                        (-and (-not-filter (-val val1) o1)
-                              (-not-filter (-val val2) o2))))]
+                        (-and (-not-filter (-val val2) o1)
+                              (-not-filter (-val val1) o2))))]
     [((tc-result1: t _ o) (tc-result1: (Value: (? ok? val))))
      (ret -Boolean (-FS (-filter (-val val) o) (-not-filter (-val val) o)))]
     [((tc-result1: (Value: (? ok? val))) (tc-result1: t _ o))
diff --git a/typed-racket-test/fail/issue-215-2.rkt b/typed-racket-test/fail/issue-215-2.rkt
new file mode 100644
index 00000000..620ba48b
--- /dev/null
+++ b/typed-racket-test/fail/issue-215-2.rkt
@@ -0,0 +1,7 @@
+#lang typed/racket
+
+
+(ann (let ((x 'b))
+       (if (equal? x 'a)
+           42
+           "foo")) Number)
diff --git a/typed-racket-test/fail/issue-215.rkt b/typed-racket-test/fail/issue-215.rkt
new file mode 100644
index 00000000..828628a3
--- /dev/null
+++ b/typed-racket-test/fail/issue-215.rkt
@@ -0,0 +1,4 @@
+#;
+(exn-pred "match:")
+#lang typed/racket
+(ann (match '(b) [(list 'a) 42]) Number)