diff --git a/tests/Unit/Http/Middleware/Api/Application/AuthenticateIPAccessTest.php b/tests/Unit/Http/Middleware/API/AuthenticateIPAccessTest.php
similarity index 91%
rename from tests/Unit/Http/Middleware/Api/Application/AuthenticateIPAccessTest.php
rename to tests/Unit/Http/Middleware/API/AuthenticateIPAccessTest.php
index cf23d0292..59b9137d9 100644
--- a/tests/Unit/Http/Middleware/Api/Application/AuthenticateIPAccessTest.php
+++ b/tests/Unit/Http/Middleware/API/AuthenticateIPAccessTest.php
@@ -1,10 +1,10 @@
 <?php
 
-namespace Tests\Unit\Http\Middleware\Api\Application;
+namespace Tests\Unit\Http\Middleware\API;
 
 use Pterodactyl\Models\ApiKey;
 use Tests\Unit\Http\Middleware\MiddlewareTestCase;
-use Pterodactyl\Http\Middleware\Api\Application\AuthenticateIPAccess;
+use Pterodactyl\Http\Middleware\Api\AuthenticateIPAccess;
 
 class AuthenticateIPAccessTest extends MiddlewareTestCase
 {
@@ -65,7 +65,7 @@ class AuthenticateIPAccessTest extends MiddlewareTestCase
     /**
      * Return an instance of the middleware to be used when testing.
      *
-     * @return \Pterodactyl\Http\Middleware\Api\Application\AuthenticateIPAccess
+     * @return \Pterodactyl\Http\Middleware\Api\AuthenticateIPAccess
      */
     private function getMiddleware(): AuthenticateIPAccess
     {
diff --git a/tests/Unit/Http/Middleware/Api/Application/AuthenticateKeyTest.php b/tests/Unit/Http/Middleware/API/AuthenticateKeyTest.php
similarity index 74%
rename from tests/Unit/Http/Middleware/Api/Application/AuthenticateKeyTest.php
rename to tests/Unit/Http/Middleware/API/AuthenticateKeyTest.php
index 486222267..354838b3f 100644
--- a/tests/Unit/Http/Middleware/Api/Application/AuthenticateKeyTest.php
+++ b/tests/Unit/Http/Middleware/API/AuthenticateKeyTest.php
@@ -1,6 +1,6 @@
 <?php
 
-namespace Tests\Unit\Http\Middleware\Api\Application;
+namespace Tests\Unit\Http\Middleware\API;
 
 use Mockery as m;
 use Cake\Chronos\Chronos;
@@ -8,10 +8,10 @@ use Pterodactyl\Models\ApiKey;
 use Illuminate\Auth\AuthManager;
 use Illuminate\Contracts\Encryption\Encrypter;
 use Tests\Unit\Http\Middleware\MiddlewareTestCase;
+use Pterodactyl\Http\Middleware\Api\AuthenticateKey;
 use Symfony\Component\HttpKernel\Exception\HttpException;
 use Pterodactyl\Exceptions\Repository\RecordNotFoundException;
 use Pterodactyl\Contracts\Repository\ApiKeyRepositoryInterface;
-use Pterodactyl\Http\Middleware\Api\Application\AuthenticateKey;
 
 class AuthenticateKeyTest extends MiddlewareTestCase
 {
@@ -51,7 +51,7 @@ class AuthenticateKeyTest extends MiddlewareTestCase
         $this->request->shouldReceive('bearerToken')->withNoArgs()->once()->andReturnNull();
 
         try {
-            $this->getMiddleware()->handle($this->request, $this->getClosureAssertions());
+            $this->getMiddleware()->handle($this->request, $this->getClosureAssertions(), ApiKey::TYPE_APPLICATION);
         } catch (HttpException $exception) {
             $this->assertEquals(401, $exception->getStatusCode());
             $this->assertEquals(['WWW-Authenticate' => 'Bearer'], $exception->getHeaders());
@@ -68,7 +68,7 @@ class AuthenticateKeyTest extends MiddlewareTestCase
         $this->request->shouldReceive('bearerToken')->withNoArgs()->twice()->andReturn('abcd1234');
         $this->repository->shouldReceive('findFirstWhere')->andThrow(new RecordNotFoundException);
 
-        $this->getMiddleware()->handle($this->request, $this->getClosureAssertions());
+        $this->getMiddleware()->handle($this->request, $this->getClosureAssertions(), ApiKey::TYPE_APPLICATION);
     }
 
     /**
@@ -90,7 +90,30 @@ class AuthenticateKeyTest extends MiddlewareTestCase
             'last_used_at' => Chronos::now(),
         ])->once()->andReturnNull();
 
-        $this->getMiddleware()->handle($this->request, $this->getClosureAssertions());
+        $this->getMiddleware()->handle($this->request, $this->getClosureAssertions(), ApiKey::TYPE_APPLICATION);
+        $this->assertEquals($model, $this->request->attributes->get('api_key'));
+    }
+
+    /**
+     * Test that a valid token can continue past the middleware when set as a user token.
+     */
+    public function testValidTokenWithUserKey()
+    {
+        $model = factory(ApiKey::class)->make();
+
+        $this->request->shouldReceive('bearerToken')->withNoArgs()->twice()->andReturn($model->identifier . 'decrypted');
+        $this->repository->shouldReceive('findFirstWhere')->with([
+            ['identifier', '=', $model->identifier],
+            ['key_type', '=', ApiKey::TYPE_ACCOUNT],
+        ])->once()->andReturn($model);
+        $this->encrypter->shouldReceive('decrypt')->with($model->token)->once()->andReturn('decrypted');
+        $this->auth->shouldReceive('guard->loginUsingId')->with($model->user_id)->once()->andReturnNull();
+
+        $this->repository->shouldReceive('withoutFreshModel->update')->with($model->id, [
+            'last_used_at' => Chronos::now(),
+        ])->once()->andReturnNull();
+
+        $this->getMiddleware()->handle($this->request, $this->getClosureAssertions(), ApiKey::TYPE_ACCOUNT);
         $this->assertEquals($model, $this->request->attributes->get('api_key'));
     }
 
@@ -111,13 +134,13 @@ class AuthenticateKeyTest extends MiddlewareTestCase
         ])->once()->andReturn($model);
         $this->encrypter->shouldReceive('decrypt')->with($model->token)->once()->andReturn('decrypted');
 
-        $this->getMiddleware()->handle($this->request, $this->getClosureAssertions());
+        $this->getMiddleware()->handle($this->request, $this->getClosureAssertions(), ApiKey::TYPE_APPLICATION);
     }
 
     /**
      * Return an instance of the middleware with mocked dependencies for testing.
      *
-     * @return \Pterodactyl\Http\Middleware\Api\Application\AuthenticateKey
+     * @return \Pterodactyl\Http\Middleware\Api\AuthenticateKey
      */
     private function getMiddleware(): AuthenticateKey
     {
diff --git a/tests/Unit/Http/Middleware/Api/Application/SetSessionDriverTest.php b/tests/Unit/Http/Middleware/API/SetSessionDriverTest.php
similarity index 90%
rename from tests/Unit/Http/Middleware/Api/Application/SetSessionDriverTest.php
rename to tests/Unit/Http/Middleware/API/SetSessionDriverTest.php
index 7804f8209..0f33f6735 100644
--- a/tests/Unit/Http/Middleware/Api/Application/SetSessionDriverTest.php
+++ b/tests/Unit/Http/Middleware/API/SetSessionDriverTest.php
@@ -1,13 +1,13 @@
 <?php
 
-namespace Tests\Unit\Http\Middleware\Api\Application;
+namespace Tests\Unit\Http\Middleware\API;
 
 use Mockery as m;
 use Barryvdh\Debugbar\LaravelDebugbar;
 use Illuminate\Contracts\Config\Repository;
 use Illuminate\Contracts\Foundation\Application;
 use Tests\Unit\Http\Middleware\MiddlewareTestCase;
-use Pterodactyl\Http\Middleware\Api\Application\SetSessionDriver;
+use Pterodactyl\Http\Middleware\Api\SetSessionDriver;
 
 class SetSessionDriverTest extends MiddlewareTestCase
 {
@@ -60,7 +60,7 @@ class SetSessionDriverTest extends MiddlewareTestCase
     /**
      * Return an instance of the middleware with mocked dependencies for testing.
      *
-     * @return \Pterodactyl\Http\Middleware\Api\Application\SetSessionDriver
+     * @return \Pterodactyl\Http\Middleware\Api\SetSessionDriver
      */
     private function getMiddleware(): SetSessionDriver
     {