diff --git a/test/parallel/test-http-invalid-path-chars.js b/test/parallel/test-http-invalid-path-chars.js
new file mode 100644
index 00000000000..462e0bc12a0
--- /dev/null
+++ b/test/parallel/test-http-invalid-path-chars.js
@@ -0,0 +1,20 @@
+'use strict';
+const common = require('../common');
+const assert = require('assert');
+const http = require('http');
+
+const expectedError = /^TypeError: Request path contains unescaped characters$/;
+const theExperimentallyDeterminedNumber = 39;
+
+function fail(path) {
+  assert.throws(() => {
+    http.request({ path }, common.fail);
+  }, expectedError);
+}
+
+for (let i = 0; i <= theExperimentallyDeterminedNumber; i++) {
+  const prefix = 'a'.repeat(i);
+  for (let i = 0; i <= 32; i++) {
+    fail(prefix + String.fromCodePoint(i));
+  }
+}