diff --git a/src/Illuminate/Foundation/Testing/PendingCommand.php b/src/Illuminate/Foundation/Testing/PendingCommand.php
index 379eba14c8d7..d217c0261c92 100644
--- a/src/Illuminate/Foundation/Testing/PendingCommand.php
+++ b/src/Illuminate/Foundation/Testing/PendingCommand.php
@@ -165,7 +165,6 @@ protected function mockConsoleOutput()
 
         foreach ($this->test->expectedQuestions as $i => $question) {
             $mock->shouldReceive('askQuestion')
-                ->once()
                 ->ordered()
                 ->with(Mockery::on(function ($argument) use ($question) {
                     return $argument->getQuestion() == $question[0];
@@ -195,7 +194,6 @@ private function createABufferedOutputMock()
 
         foreach ($this->test->expectedOutput as $i => $output) {
             $mock->shouldReceive('doWrite')
-                ->once()
                 ->ordered()
                 ->with($output, Mockery::any())
                 ->andReturnUsing(function () use ($i) {
diff --git a/src/Illuminate/Foundation/Testing/TestCase.php b/src/Illuminate/Foundation/Testing/TestCase.php
index f712d80b0f4b..5c20d0c44f32 100644
--- a/src/Illuminate/Foundation/Testing/TestCase.php
+++ b/src/Illuminate/Foundation/Testing/TestCase.php
@@ -42,6 +42,13 @@ abstract class TestCase extends BaseTestCase
      */
     protected $beforeApplicationDestroyedCallbacks = [];
 
+    /**
+     * The exception thrown while running an application destruction callback.
+     *
+     * @var \Throwable
+     */
+    protected $callbackException;
+
     /**
      * Indicates if we have made it through the base setUp function.
      *
@@ -136,9 +143,7 @@ protected function setUpTraits()
     protected function tearDown(): void
     {
         if ($this->app) {
-            foreach ($this->beforeApplicationDestroyedCallbacks as $callback) {
-                call_user_func($callback);
-            }
+            $this->callBeforeApplicationDestroyedCallbacks();
 
             $this->app->flush();
 
@@ -175,6 +180,10 @@ protected function tearDown(): void
         $this->beforeApplicationDestroyedCallbacks = [];
 
         Artisan::forgetBootstrappers();
+
+        if ($this->callbackException) {
+            throw $this->callbackException;
+        }
     }
 
     /**
@@ -202,4 +211,22 @@ protected function beforeApplicationDestroyed(callable $callback)
     {
         $this->beforeApplicationDestroyedCallbacks[] = $callback;
     }
+
+    /**
+     * Execute the application's pre-destruction callbacks.
+     *
+     * @return void
+     */
+    protected function callBeforeApplicationDestroyedCallbacks()
+    {
+        foreach ($this->beforeApplicationDestroyedCallbacks as $callback) {
+            try {
+                call_user_func($callback);
+            } catch (\Throwable $e) {
+                if (! $this->callbackException) {
+                    $this->callbackException = $e;
+                }
+            }
+        }
+    }
 }