diff --git a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/fail/error-pruning1.rkt b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/fail/error-pruning1.rkt
new file mode 100644
index 0000000000..0e37e7cfe0
--- /dev/null
+++ b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/fail/error-pruning1.rkt
@@ -0,0 +1,11 @@
+#;
+(exn-pred #px"^((?!Integer).)+$")
+#lang typed/racket
+
+;; Tests that function type pruning in errors is working. If the string
+;; "Integer" shows up the error (which should be about Number), then
+;; pruning is broken.
+;; Because `exn-pred' only checks the first line of the error, only one
+;; error expression per file (otherwise, the first line is a summary).
+
+(add1 'foo1)
diff --git a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/fail/error-pruning2.rkt b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/fail/error-pruning2.rkt
new file mode 100644
index 0000000000..1fe5967fc1
--- /dev/null
+++ b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/fail/error-pruning2.rkt
@@ -0,0 +1,11 @@
+#;
+(exn-pred #px"^((?!Integer).)+$")
+#lang typed/racket
+
+;; Tests that function type pruning in errors is working. If the string
+;; "Integer" shows up the error (which should be about Number), then
+;; pruning is broken.
+;; Because `exn-pred' only checks the first line of the error, only one
+;; error expression per file (otherwise, the first line is a summary).
+
+(+ 'foo1 3)
diff --git a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/fail/error-pruning3.rkt b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/fail/error-pruning3.rkt
new file mode 100644
index 0000000000..3222394075
--- /dev/null
+++ b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/fail/error-pruning3.rkt
@@ -0,0 +1,11 @@
+#;
+(exn-pred #px"^((?!Integer).)+$")
+#lang typed/racket
+
+;; Tests that function type pruning in errors is working. If the string
+;; "Integer" shows up the error (which should be about Number), then
+;; pruning is broken.
+;; Because `exn-pred' only checks the first line of the error, only one
+;; error expression per file (otherwise, the first line is a summary).
+
+(+ 'foo1 "a")