diff --git a/tests/php/Control/DirectorTest.php b/tests/php/Control/DirectorTest.php
index cb2e94b62..a7095cf1a 100644
--- a/tests/php/Control/DirectorTest.php
+++ b/tests/php/Control/DirectorTest.php
@@ -1,5 +1,4 @@
 <?php
-
 namespace SilverStripe\Control\Tests;
 
 use SilverStripe\Control\Cookie_Backend;
@@ -13,6 +12,7 @@ use SilverStripe\Control\Tests\DirectorTest\TestController;
 use SilverStripe\Core\Injector\Injector;
 use SilverStripe\Core\Kernel;
 use SilverStripe\Dev\SapphireTest;
+use SilverStripe\Core\Config\Config;
 
 /**
  * @todo test Director::alternateBaseFolder()
@@ -646,4 +646,76 @@ class DirectorTest extends SapphireTest
         // preCall 'true' will trigger an exception and prevent post call execution
         $this->assertEquals(2, $filter->postCalls);
     }
+
+    public function testGlobalMiddleware()
+    {
+        $middleware = new DirectorTest\TestMiddleware;
+
+        Injector::inst()->registerService($middleware, 'Middleware1');
+        Config::modify()->set(Director::class, 'middlewares', [ 'Middleware1' ]);
+
+        $response = Director::test('some-dummy-url');
+        $this->assertEquals(404, $response->getStatusCode());
+
+        // Both triggered
+        $this->assertEquals(1, $middleware->preCalls);
+        $this->assertEquals(1, $middleware->postCalls);
+
+        $middleware->failPost = true;
+
+        $response = Director::test('some-dummy-url');
+        $this->assertEquals(500, $response->getStatusCode());
+
+        // Both triggered
+        $this->assertEquals(2, $middleware->preCalls);
+        $this->assertEquals(2, $middleware->postCalls);
+
+        $middleware->failPre = true;
+
+        $response = Director::test('some-dummy-url');
+        $this->assertEquals(400, $response->getStatusCode());
+
+        // Pre triggered, post not
+        $this->assertEquals(3, $middleware->preCalls);
+        $this->assertEquals(2, $middleware->postCalls);
+    }
+
+    public function testRouteSpecificMiddleware()
+    {
+        $middleware = new DirectorTest\TestMiddleware;
+        $specificMiddleware = new DirectorTest\TestMiddleware;
+
+        Injector::inst()->registerService($middleware, 'Middleware1');
+        Injector::inst()->registerService($specificMiddleware, 'Middleware2');
+
+        // Global middleware
+        Config::modify()->set(Director::class, 'middlewares', [ 'Middleware1' ]);
+
+        // URL rules, one of which has a specific middleware
+        Config::modify()->set(
+            Director::class,
+            'rules',
+            [
+                'url-one' => TestController::class,
+                'url-two' => [
+                    'Controller' => TestController::class,
+                    'Middlewares' => [ 'Middleware2' ]
+                ]
+            ]
+        );
+
+        // URL without a route-specific middleware
+        $response = Director::test('url-one');
+
+        // Only the global middleware triggered
+        $this->assertEquals(1, $middleware->preCalls);
+        $this->assertEquals(0, $specificMiddleware->postCalls);
+
+        $response = Director::test('url-two');
+
+        // Both triggered on the url with the specific middleware applied
+        $this->assertEquals(2, $middleware->preCalls);
+        $this->assertEquals(1, $specificMiddleware->postCalls);
+
+    }
 }
diff --git a/tests/php/Control/DirectorTest/TestMiddleware.php b/tests/php/Control/DirectorTest/TestMiddleware.php
new file mode 100644
index 000000000..d26e4a727
--- /dev/null
+++ b/tests/php/Control/DirectorTest/TestMiddleware.php
@@ -0,0 +1,40 @@
+<?php
+
+namespace SilverStripe\Control\Tests\DirectorTest;
+
+use SilverStripe\Control\HTTPRequest;
+use SilverStripe\Control\HTTPResponse;
+use SilverStripe\Control\HTTPMiddleware;
+use SilverStripe\Dev\TestOnly;
+
+class TestMiddleware implements HTTPMiddleware, TestOnly
+{
+    public $preCalls = 0;
+    public $postCalls = 0;
+
+    public $failPre = false;
+    public $failPost = false;
+
+    public function process(HTTPRequest $request, callable $delegate)
+    {
+        $this->preCalls++;
+        if ($this->failPre) {
+            return new HTTPResponse('Fail pre', 400);
+        }
+
+        $response = $delegate($request);
+
+        $this->postCalls++;
+        if ($this->failPost) {
+            return new HTTPResponse('Fail post', 500);
+        }
+
+        return $response;
+    }
+
+    public function reset()
+    {
+        $this->preCalls = 0;
+        $this->postCalls = 0;
+    }
+}