diff --git a/tests/integration/run_tests.rs b/tests/integration/run_tests.rs
index 6419f6ff0f01a8..bac2fc77442449 100644
--- a/tests/integration/run_tests.rs
+++ b/tests/integration/run_tests.rs
@@ -1694,14 +1694,22 @@ fn type_directives_js_main() {
   assert_not_contains!(output.combined_output(), "type_reference.d.ts");
 }
 
+itest!(test_import_assertions {
+  args: "run --reload run/deno_import_assertions.ts",
+  output: "run/deno_import_assertions.ts.out",
+});
+
+// TODO(petamoriken): Need to quit TypeScript transpiling `assert` to `with` in deno_ast
 #[test]
-fn test_deno_futures_env() {
+fn test_import_assertions_with_deno_futures_env() {
   let context = TestContextBuilder::new().add_future_env_vars().build();
   let output = context
     .new_command()
-    .args("run --quiet --reload run/deno_futures_env.ts")
+    .args("run --quiet --reload run/deno_import_assertions.ts")
     .run();
-  output.assert_exit_code(0);
+  output
+    .assert_exit_code(1)
+    .assert_matches_file("run/deno_import_assertions.ts.out2");
 }
 
 itest!(type_directives_redirect {
diff --git a/tests/testdata/run/deno_futures_env.ts b/tests/testdata/run/deno_futures_env.ts
deleted file mode 100644
index 21f76e367560e4..00000000000000
--- a/tests/testdata/run/deno_futures_env.ts
+++ /dev/null
@@ -1,3 +0,0 @@
-if (typeof window !== "undefined") {
-  throw new Error("Window global available");
-}
diff --git a/tests/testdata/run/deno_import_assertions.json b/tests/testdata/run/deno_import_assertions.json
new file mode 100644
index 00000000000000..ea1a43e3b4b798
--- /dev/null
+++ b/tests/testdata/run/deno_import_assertions.json
@@ -0,0 +1,3 @@
+{
+  "foo": "foo"
+}
\ No newline at end of file
diff --git a/tests/testdata/run/deno_import_assertions.ts b/tests/testdata/run/deno_import_assertions.ts
new file mode 100644
index 00000000000000..f3e594a821bd8f
--- /dev/null
+++ b/tests/testdata/run/deno_import_assertions.ts
@@ -0,0 +1,2 @@
+import foo from "./deno_import_assertions.json" assert { type: "json" };
+console.log(foo);
diff --git a/tests/testdata/run/deno_import_assertions.ts.out b/tests/testdata/run/deno_import_assertions.ts.out
new file mode 100644
index 00000000000000..70ec274d9afb99
--- /dev/null
+++ b/tests/testdata/run/deno_import_assertions.ts.out
@@ -0,0 +1 @@
+{ foo: "foo" }
diff --git a/tests/testdata/run/deno_import_assertions.ts.out2 b/tests/testdata/run/deno_import_assertions.ts.out2
new file mode 100644
index 00000000000000..e7710fa8786b80
--- /dev/null
+++ b/tests/testdata/run/deno_import_assertions.ts.out2
@@ -0,0 +1,4 @@
+error: Uncaught SyntaxError: Unexpected identifier 'assert'
+import foo from "./deno_import_assertions.json" assert { type: "json" };
+                                                ^
+    at <anonymous> (file:///[WILDCARD]/deno_import_assertions.js:[WILDCARD])