diff --git a/lib/__tests__/standalone-glob-parent-test/folder/another-folder/standalone-glob-parent-wildcard.test.js b/lib/__tests__/standalone-glob-parent-test/folder/another-folder/standalone-glob-parent-wildcard.test.js
new file mode 100644
index 0000000000..ae28098c80
--- /dev/null
+++ b/lib/__tests__/standalone-glob-parent-test/folder/another-folder/standalone-glob-parent-wildcard.test.js
@@ -0,0 +1,20 @@
+'use strict';
+
+const standalone = require('../../../../standalone');
+
+it('glob contains a parent directory and ** wildcard', async () => {
+	const { results } = await standalone({
+		files: '../**/sibling-style.css',
+		config: { rules: { 'block-no-empty': true } },
+		cwd: __dirname,
+	});
+
+	expect(results).toHaveLength(1);
+	expect(results[0].errored).toBe(true);
+	expect(results[0].warnings[0]).toEqual(
+		expect.objectContaining({
+			rule: 'block-no-empty',
+			severity: 'error',
+		}),
+	);
+});
diff --git a/lib/__tests__/standalone-glob-parent-test/folder/sibling/sibling-style.css b/lib/__tests__/standalone-glob-parent-test/folder/sibling/sibling-style.css
new file mode 100644
index 0000000000..b978c1b598
--- /dev/null
+++ b/lib/__tests__/standalone-glob-parent-test/folder/sibling/sibling-style.css
@@ -0,0 +1 @@
+a {}
\ No newline at end of file
diff --git a/lib/__tests__/standalone-glob-parent-test/folder/standalone-glob-parent.test.js b/lib/__tests__/standalone-glob-parent-test/folder/standalone-glob-parent.test.js
new file mode 100644
index 0000000000..04a65ead6c
--- /dev/null
+++ b/lib/__tests__/standalone-glob-parent-test/folder/standalone-glob-parent.test.js
@@ -0,0 +1,20 @@
+'use strict';
+
+const standalone = require('../../../standalone');
+
+it('glob has parent directory', async () => {
+	const { results } = await standalone({
+		files: '../parent-folder-style.css',
+		config: { rules: { 'block-no-empty': true } },
+		cwd: __dirname,
+	});
+
+	expect(results).toHaveLength(1);
+	expect(results[0].errored).toBe(true);
+	expect(results[0].warnings[0]).toEqual(
+		expect.objectContaining({
+			rule: 'block-no-empty',
+			severity: 'error',
+		}),
+	);
+});
diff --git a/lib/__tests__/standalone-glob-parent-test/parent-folder-style.css b/lib/__tests__/standalone-glob-parent-test/parent-folder-style.css
new file mode 100644
index 0000000000..b978c1b598
--- /dev/null
+++ b/lib/__tests__/standalone-glob-parent-test/parent-folder-style.css
@@ -0,0 +1 @@
+a {}
\ No newline at end of file