diff --git a/app/config/default.php b/app/config/default.php
index 62099034..6f530ed8 100755
--- a/app/config/default.php
+++ b/app/config/default.php
@@ -424,4 +424,17 @@
         'entrypoints' => 'assets://entrypoints.json',
         'manifest'    => 'assets://manifest.json',
     ],
+
+    /**
+     * ----------------------------------------------------------------------
+     * Writable Stream Config
+     * ----------------------------------------------------------------------
+     * Resource stream to check for write permission. True means it should be
+     * writeable, false means it should not be writable.
+     */
+    'writable' => [
+        'logs://'     => true,
+        'cache://'    => true,
+        'sessions://' => true,
+    ],
 ];
diff --git a/app/config/testing.php b/app/config/testing.php
index 86077739..e774f0ce 100755
--- a/app/config/testing.php
+++ b/app/config/testing.php
@@ -74,4 +74,13 @@
     'session' => [
         'handler' => env('TEST_SESSION_HANDLER', 'array'),
     ],
+
+    /*
+     * Don't force writable directories in tests.
+     */
+    'writable' => [
+        'logs://'     => null,
+        'cache://'    => null,
+        'sessions://' => null,
+    ],
 ];
diff --git a/app/src/Core.php b/app/src/Core.php
index 9efd5c5b..b840e50e 100644
--- a/app/src/Core.php
+++ b/app/src/Core.php
@@ -56,6 +56,7 @@
 use UserFrosting\Sprinkle\Core\Listeners\ModelInitiated;
 use UserFrosting\Sprinkle\Core\Listeners\ResourceLocatorInitiated;
 use UserFrosting\Sprinkle\Core\Listeners\SetRouteCaching;
+use UserFrosting\Sprinkle\Core\Middlewares\FilePermissionMiddleware;
 use UserFrosting\Sprinkle\Core\Middlewares\LocaleMiddleware;
 use UserFrosting\Sprinkle\Core\Middlewares\SessionMiddleware;
 use UserFrosting\Sprinkle\Core\Middlewares\URIMiddleware;
@@ -211,6 +212,7 @@ public function getMiddlewares(): array
             CsrfGuardMiddleware::class,
             SessionMiddleware::class,
             URIMiddleware::class,
+            FilePermissionMiddleware::class,
             ExceptionHandlerMiddleware::class,
         ];
     }
diff --git a/app/src/Middlewares/FilePermissionMiddleware.php b/app/src/Middlewares/FilePermissionMiddleware.php
new file mode 100644
index 00000000..096c31be
--- /dev/null
+++ b/app/src/Middlewares/FilePermissionMiddleware.php
@@ -0,0 +1,65 @@
+<?php
+
+declare(strict_types=1);
+
+/*
+ * UserFrosting Core Sprinkle (http://www.userfrosting.com)
+ *
+ * @link      https://github.com/userfrosting/sprinkle-core
+ * @copyright Copyright (c) 2021 Alexander Weissman & Louis Charette
+ * @license   https://github.com/userfrosting/sprinkle-core/blob/master/LICENSE.md (MIT License)
+ */
+
+namespace UserFrosting\Sprinkle\Core\Middlewares;
+
+use Psr\Http\Message\ResponseInterface;
+use Psr\Http\Message\ServerRequestInterface;
+use Psr\Http\Server\MiddlewareInterface;
+use Psr\Http\Server\RequestHandlerInterface;
+use UserFrosting\Config\Config;
+use UserFrosting\Sprinkle\Core\Exceptions\BadConfigException;
+use UserFrosting\UniformResourceLocator\ResourceLocatorInterface;
+
+/**
+ * Middleware used to check if the file permissions are correct.
+ */
+class FilePermissionMiddleware implements MiddlewareInterface
+{
+    /**
+     * Inject dependencies
+     *
+     * @param ResourceLocatorInterface $locator
+     * @param Config                   $config
+     */
+    public function __construct(
+        protected ResourceLocatorInterface $locator,
+        protected Config $config,
+    ) {
+    }
+
+    /**
+     * {@inheritdoc}
+     */
+    public function process(ServerRequestInterface $request, RequestHandlerInterface $handler): ResponseInterface
+    {
+        foreach ($this->config->get('writable') as $stream => $assertWriteable) {
+            // Since config can't be removed, we skip if the value is null
+            if ($assertWriteable === null) {
+                continue;
+            }
+
+            // Translate stream to file path
+            $file = $this->locator->findResource($stream);
+
+            // Check if file exist and is writeable
+            if ($file === null || $assertWriteable !== is_writable($file)) {
+                // If file doesn't exist, we try to find the expected path
+                $expectedPath = $this->locator->findResource($stream, false, true);
+
+                throw new BadConfigException("Stream $stream doesn't exist and is not writeable. Make sure path `$expectedPath` exist and is writeable.");
+            }
+        }
+
+        return $handler->handle($request);
+    }
+}
diff --git a/app/tests/Unit/Middlewares/FilePermissionMiddlewareTest.php b/app/tests/Unit/Middlewares/FilePermissionMiddlewareTest.php
new file mode 100644
index 00000000..e2238bb1
--- /dev/null
+++ b/app/tests/Unit/Middlewares/FilePermissionMiddlewareTest.php
@@ -0,0 +1,155 @@
+<?php
+
+declare(strict_types=1);
+
+/*
+ * UserFrosting Core Sprinkle (http://www.userfrosting.com)
+ *
+ * @link      https://github.com/userfrosting/sprinkle-core
+ * @copyright Copyright (c) 2021 Alexander Weissman & Louis Charette
+ * @license   https://github.com/userfrosting/sprinkle-core/blob/master/LICENSE.md (MIT License)
+ */
+
+namespace UserFrosting\Sprinkle\Core\Tests\Unit\Middlewares;
+
+use Mockery;
+use Mockery\Adapter\Phpunit\MockeryPHPUnitIntegration;
+use phpmock\mockery\PHPMockery;
+use PHPUnit\Framework\TestCase;
+use Psr\Http\Message\ResponseInterface;
+use Psr\Http\Message\ServerRequestInterface;
+use Psr\Http\Server\RequestHandlerInterface;
+use ReflectionClass;
+use UserFrosting\Config\Config;
+use UserFrosting\Sprinkle\Core\Exceptions\BadConfigException;
+use UserFrosting\Sprinkle\Core\Middlewares\FilePermissionMiddleware;
+use UserFrosting\UniformResourceLocator\ResourceLocatorInterface;
+
+class FilePermissionMiddlewareTest extends TestCase
+{
+    use MockeryPHPUnitIntegration;
+
+    public function testWithPathNotFound(): void
+    {
+        $config = new Config([
+            'writable' => [
+                'foo://' => true,
+            ],
+        ]);
+
+        /** @var RequestHandlerInterface */
+        $handler = Mockery::mock(RequestHandlerInterface::class)
+            ->shouldNotReceive('handle')
+            ->getMock();
+
+        /** @var ServerRequestInterface */
+        $request = Mockery::mock(ServerRequestInterface::class);
+
+        /** @var ResourceLocatorInterface */
+        $locator = Mockery::mock(ResourceLocatorInterface::class)
+            ->shouldReceive('findResource')->once()->with('foo://')->andReturn(null)
+            ->shouldReceive('findResource')->once()->with('foo://', false, true)->andReturn('app/foo')
+            ->getMock();
+
+        // Set Expectation
+        $this->expectException(BadConfigException::class);
+        $this->expectExceptionMessage("Stream foo:// doesn't exist and is not writeable. Make sure path `app/foo` exist and is writeable.");
+
+        $middleware = new FilePermissionMiddleware($locator, $config);
+        $middleware->process($request, $handler);
+    }
+
+    public function testWithWritable(): void
+    {
+        $config = new Config([
+            'writable' => [
+                'foo://' => true,
+            ],
+        ]);
+
+        // Mock built-in is_writable
+        $reflection_class = new ReflectionClass(FilePermissionMiddleware::class);
+        $namespace = $reflection_class->getNamespaceName();
+        PHPMockery::mock($namespace, 'is_writable')->andReturn(true);
+
+        /** @var RequestHandlerInterface */
+        $handler = Mockery::mock(RequestHandlerInterface::class)
+            ->shouldReceive('handle')
+            ->once()
+            ->with(Mockery::type(ServerRequestInterface::class))
+            ->andReturn(Mockery::mock(ResponseInterface::class))
+            ->getMock();
+
+        /** @var ServerRequestInterface */
+        $request = Mockery::mock(ServerRequestInterface::class);
+
+        /** @var ResourceLocatorInterface */
+        $locator = Mockery::mock(ResourceLocatorInterface::class)
+            ->shouldReceive('findResource')->once()->with('foo://')->andReturn('app/foo')
+            ->getMock();
+
+        $middleware = new FilePermissionMiddleware($locator, $config);
+        $middleware->process($request, $handler);
+    }
+
+    public function testWithNotWritable(): void
+    {
+        $config = new Config([
+            'writable' => [
+                'foo://' => true,
+            ],
+        ]);
+
+        // Mock built-in is_writable
+        $reflection_class = new ReflectionClass(FilePermissionMiddleware::class);
+        $namespace = $reflection_class->getNamespaceName();
+        PHPMockery::mock($namespace, 'is_writable')->andReturn(false);
+
+        /** @var RequestHandlerInterface */
+        $handler = Mockery::mock(RequestHandlerInterface::class)
+            ->shouldNotReceive('handle')
+            ->getMock();
+
+        /** @var ServerRequestInterface */
+        $request = Mockery::mock(ServerRequestInterface::class);
+
+        /** @var ResourceLocatorInterface */
+        $locator = Mockery::mock(ResourceLocatorInterface::class)
+            ->shouldReceive('findResource')->once()->with('foo://')->andReturn('app/foo')
+            ->shouldReceive('findResource')->once()->with('foo://', false, true)->andReturn('app/foo')
+            ->getMock();
+
+        // Set Expectation
+        $this->expectException(BadConfigException::class);
+        $this->expectExceptionMessage("Stream foo:// doesn't exist and is not writeable. Make sure path `app/foo` exist and is writeable.");
+
+        $middleware = new FilePermissionMiddleware($locator, $config);
+        $middleware->process($request, $handler);
+    }
+
+    public function testWithNotConfig(): void
+    {
+        $config = new Config([
+            'writable' => [
+                'foo://' => null,
+            ],
+        ]);
+
+        /** @var RequestHandlerInterface */
+        $handler = Mockery::mock(RequestHandlerInterface::class)
+            ->shouldNotReceive('handle')
+            ->once()
+            ->with(Mockery::type(ServerRequestInterface::class))
+            ->andReturn(Mockery::mock(ResponseInterface::class))
+            ->getMock();
+
+        /** @var ServerRequestInterface */
+        $request = Mockery::mock(ServerRequestInterface::class);
+
+        /** @var ResourceLocatorInterface */
+        $locator = Mockery::mock(ResourceLocatorInterface::class);
+
+        $middleware = new FilePermissionMiddleware($locator, $config);
+        $middleware->process($request, $handler);
+    }
+}