diff --git a/lib/Middleware/ExceptionMiddleware.php b/lib/Middleware/ExceptionMiddleware.php
index aa0fdb5f1..0c59a5e17 100644
--- a/lib/Middleware/ExceptionMiddleware.php
+++ b/lib/Middleware/ExceptionMiddleware.php
@@ -32,6 +32,7 @@ use OCP\AppFramework\Http\JSONResponse;
 use OCP\AppFramework\OCS\OCSException;
 use OCP\AppFramework\OCSController;
 use OCP\ILogger;
+use OCP\IRequest;
 use OCP\Util;
 use OCP\IConfig;
 
@@ -41,6 +42,8 @@ class ExceptionMiddleware extends Middleware {
 	private $logger;
 	/** @var IConfig */
 	private $config;
+	/** @var IRequest */
+	private $request;
 
 	/**
 	 * SharingMiddleware constructor.
@@ -48,9 +51,10 @@ class ExceptionMiddleware extends Middleware {
 	 * @param ILogger $logger
 	 * @param IConfig $config
 	 */
-	public function __construct(ILogger $logger, IConfig $config) {
+	public function __construct(ILogger $logger, IConfig $config, IRequest $request) {
 		$this->logger = $logger;
 		$this->config = $config;
+		$this->request = $request;
 	}
 
 	/**
@@ -67,43 +71,10 @@ class ExceptionMiddleware extends Middleware {
 			throw $exception;
 		}
 
-		if ($exception instanceof ConflictException) {
-			if ($this->config->getSystemValue('loglevel', Util::WARN) === Util::DEBUG) {
-				$this->logger->logException($exception);
-			}
-			return new JSONResponse([
-				'status' => $exception->getStatus(),
-				'message' => $exception->getMessage(),
-				'data' => $exception->getData(),
-			], $exception->getStatus());
-		}
-		
-		if ($exception instanceof StatusException) {
-			if ($this->config->getSystemValue('loglevel', Util::WARN) === Util::DEBUG) {
-				$this->logger->logException($exception);
-			}
-
-			if ($controller instanceof OCSController) {
-				$exception = new OCSException($exception->getMessage(), $exception->getStatus(), $exception);
-				throw $exception;
-			}
-			return new JSONResponse([
-				'status' => $exception->getStatus(),
-				'message' => $exception->getMessage()
-			], $exception->getStatus());
-		}
-
-		if (strpos(get_class($controller), 'OCA\\Deck\\Controller\\') === 0) {
-			$response = [
-				'status' => 500,
-				'message' => $exception->getMessage()
-			];
-			$this->logger->logException($exception);
-			if ($this->config->getSystemValue('debug', true) === true) {
-				$response['exception'] = (array) $exception;
-			}
-			return new JSONResponse($response, 500);
-		}
+		$debugMode = $this->config->getSystemValue('debug', false);
+		$exceptionMessage = $debugMode !== true
+			? 'Internal server error: Please contact the server administrator if this error reappears multiple times, please include the request ID "' . $this->request->getId() . '" below in your report.'
+			: $exception->getMessage();
 
 		// uncatched DoesNotExistExceptions will be thrown when the main entity is not found
 		// we return a 403 so we don't leak information over existing entries
@@ -114,6 +85,43 @@ class ExceptionMiddleware extends Middleware {
 				'message' => 'Permission denied'
 			], 403);
 		}
+		
+		if ($exception instanceof StatusException) {
+			if ($this->config->getSystemValue('loglevel', Util::WARN) === Util::DEBUG) {
+				$this->logger->logException($exception);
+			}
+
+			if ($exception instanceof ConflictException) {
+				return new JSONResponse([
+					'status' => $exception->getStatus(),
+					'message' => $exception->getMessage(),
+					'data' => $exception->getData(),
+				], $exception->getStatus());
+			}
+
+			if ($controller instanceof OCSController) {
+				$exception = new OCSException($exception->getMessage(), $exception->getStatus(), $exception);
+				throw $exception;
+			}
+
+			return new JSONResponse([
+				'status' => $exception->getStatus(),
+				'message' => $exception->getMessage(),
+			], $exception->getStatus());
+		}
+
+		if (strpos(get_class($controller), 'OCA\\Deck\\Controller\\') === 0) {
+			$response = [
+				'status' => 500,
+				'message' => $exceptionMessage,
+				'requestId' => $this->request->getId(),
+			];
+			$this->logger->logException($exception);
+			if ($debugMode === true) {
+				$response['exception'] = (array) $exception;
+			}
+			return new JSONResponse($response, 500);
+		}
 
 		throw $exception;
 	}
diff --git a/lib/StatusException.php b/lib/StatusException.php
index 6e88cf009..0c0ce00ef 100644
--- a/lib/StatusException.php
+++ b/lib/StatusException.php
@@ -23,6 +23,12 @@
 
 namespace OCA\Deck;
 
+/**
+ * User facing exception that can be thrown with an error being reported to the frontend
+ * or consumers of the API
+ *
+ * This exception is catched in the ExceptionMiddleware
+ */
 class StatusException extends \Exception {
 	public function __construct($message) {
 		parent::__construct($message);
diff --git a/tests/unit/Middleware/ExceptionMiddlewareTest.php b/tests/unit/Middleware/ExceptionMiddlewareTest.php
index d7df3ac1d..dc00ac40a 100644
--- a/tests/unit/Middleware/ExceptionMiddlewareTest.php
+++ b/tests/unit/Middleware/ExceptionMiddlewareTest.php
@@ -47,10 +47,12 @@ class ExceptionMiddlewareTest extends \Test\TestCase {
 	public function setUp(): void {
 		$this->logger = $this->createMock(ILogger::class);
 		$this->config = $this->createMock(IConfig::class);
+		$this->request = $this->createMock(IRequest::class);
 		$this->controller = $this->createMock(Controller::class);
 		$this->exceptionMiddleware = new ExceptionMiddleware(
 			$this->logger,
-			$this->config
+			$this->config,
+			$this->request
 		);
 	}
 
@@ -81,10 +83,11 @@ class ExceptionMiddlewareTest extends \Test\TestCase {
 	}
 
 	public function testAfterExceptionFail() {
+		$this->request->expects($this->any())->method('getId')->willReturn('abc123');
 		// BoardService $boardService, PermissionService $permissionService, $userId
 		$boardController = new BoardController('deck', $this->createMock(IRequest::class), $this->createMock(BoardService::class), $this->createMock(PermissionService::class), 'admin');
-		$result = $this->exceptionMiddleware->afterException($boardController, 'bar', new \Exception('failed hard'));
-		$this->assertEquals('failed hard', $result->getData()['message']);
+		$result = $this->exceptionMiddleware->afterException($boardController, 'bar', new \Exception('other exception message'));
+		$this->assertEquals('Internal server error: Please contact the server administrator if this error reappears multiple times, please include the request ID "abc123" below in your report.', $result->getData()['message']);
 		$this->assertEquals(500, $result->getData()['status']);
 	}
 }