diff --git a/app/Jobs/ApplicationDeploymentJob.php b/app/Jobs/ApplicationDeploymentJob.php
index 349fccb50..5dced0599 100644
--- a/app/Jobs/ApplicationDeploymentJob.php
+++ b/app/Jobs/ApplicationDeploymentJob.php
@@ -976,7 +976,7 @@ private function push_to_docker_registry()
         } catch (Exception $e) {
             $this->application_deployment_queue->addLogEntry('Failed to push image to docker registry. Please check debug logs for more information.');
             if ($forceFail) {
-                throw new DeploymentException($e->getMessage(), 69420);
+                throw new DeploymentException(get_class($e).': '.$e->getMessage(), $e->getCode(), $e);
             }
         }
     }
@@ -1610,123 +1610,131 @@ private function laravel_finetunes()
 
     private function rolling_update()
     {
-        $this->checkForCancellation();
-        if ($this->server->isSwarm()) {
-            $this->application_deployment_queue->addLogEntry('Rolling update started.');
-            $this->execute_remote_command(
-                [
-                    executeInDocker($this->deployment_uuid, "docker stack deploy --detach=true --with-registry-auth -c {$this->workdir}{$this->docker_compose_location} {$this->application->uuid}"),
-                ],
-            );
-            $this->application_deployment_queue->addLogEntry('Rolling update completed.');
-        } else {
-            if ($this->use_build_server) {
-                $this->write_deployment_configurations();
-                $this->server = $this->original_server;
-            }
-            if (count($this->application->ports_mappings_array) > 0 || (bool) $this->application->settings->is_consistent_container_name_enabled || str($this->application->settings->custom_internal_name)->isNotEmpty() || $this->pull_request_id !== 0 || str($this->application->custom_docker_run_options)->contains('--ip') || str($this->application->custom_docker_run_options)->contains('--ip6')) {
-                $this->application_deployment_queue->addLogEntry('----------------------------------------');
-                if (count($this->application->ports_mappings_array) > 0) {
-                    $this->application_deployment_queue->addLogEntry('Application has ports mapped to the host system, rolling update is not supported.');
-                }
-                if ((bool) $this->application->settings->is_consistent_container_name_enabled) {
-                    $this->application_deployment_queue->addLogEntry('Consistent container name feature enabled, rolling update is not supported.');
-                }
-                if (str($this->application->settings->custom_internal_name)->isNotEmpty()) {
-                    $this->application_deployment_queue->addLogEntry('Custom internal name is set, rolling update is not supported.');
-                }
-                if ($this->pull_request_id !== 0) {
-                    $this->application->settings->is_consistent_container_name_enabled = true;
-                    $this->application_deployment_queue->addLogEntry('Pull request deployment, rolling update is not supported.');
-                }
-                if (str($this->application->custom_docker_run_options)->contains('--ip') || str($this->application->custom_docker_run_options)->contains('--ip6')) {
-                    $this->application_deployment_queue->addLogEntry('Custom IP address is set, rolling update is not supported.');
-                }
-                $this->stop_running_container(force: true);
-                $this->start_by_compose_file();
-            } else {
-                $this->application_deployment_queue->addLogEntry('----------------------------------------');
+        try {
+            $this->checkForCancellation();
+            if ($this->server->isSwarm()) {
                 $this->application_deployment_queue->addLogEntry('Rolling update started.');
-                $this->start_by_compose_file();
-                $this->health_check();
-                $this->stop_running_container();
+                $this->execute_remote_command(
+                    [
+                        executeInDocker($this->deployment_uuid, "docker stack deploy --detach=true --with-registry-auth -c {$this->workdir}{$this->docker_compose_location} {$this->application->uuid}"),
+                    ],
+                );
                 $this->application_deployment_queue->addLogEntry('Rolling update completed.');
+            } else {
+                if ($this->use_build_server) {
+                    $this->write_deployment_configurations();
+                    $this->server = $this->original_server;
+                }
+                if (count($this->application->ports_mappings_array) > 0 || (bool) $this->application->settings->is_consistent_container_name_enabled || str($this->application->settings->custom_internal_name)->isNotEmpty() || $this->pull_request_id !== 0 || str($this->application->custom_docker_run_options)->contains('--ip') || str($this->application->custom_docker_run_options)->contains('--ip6')) {
+                    $this->application_deployment_queue->addLogEntry('----------------------------------------');
+                    if (count($this->application->ports_mappings_array) > 0) {
+                        $this->application_deployment_queue->addLogEntry('Application has ports mapped to the host system, rolling update is not supported.');
+                    }
+                    if ((bool) $this->application->settings->is_consistent_container_name_enabled) {
+                        $this->application_deployment_queue->addLogEntry('Consistent container name feature enabled, rolling update is not supported.');
+                    }
+                    if (str($this->application->settings->custom_internal_name)->isNotEmpty()) {
+                        $this->application_deployment_queue->addLogEntry('Custom internal name is set, rolling update is not supported.');
+                    }
+                    if ($this->pull_request_id !== 0) {
+                        $this->application->settings->is_consistent_container_name_enabled = true;
+                        $this->application_deployment_queue->addLogEntry('Pull request deployment, rolling update is not supported.');
+                    }
+                    if (str($this->application->custom_docker_run_options)->contains('--ip') || str($this->application->custom_docker_run_options)->contains('--ip6')) {
+                        $this->application_deployment_queue->addLogEntry('Custom IP address is set, rolling update is not supported.');
+                    }
+                    $this->stop_running_container(force: true);
+                    $this->start_by_compose_file();
+                } else {
+                    $this->application_deployment_queue->addLogEntry('----------------------------------------');
+                    $this->application_deployment_queue->addLogEntry('Rolling update started.');
+                    $this->start_by_compose_file();
+                    $this->health_check();
+                    $this->stop_running_container();
+                    $this->application_deployment_queue->addLogEntry('Rolling update completed.');
+                }
             }
+        } catch (Exception $e) {
+            throw new DeploymentException('Rolling update failed ('.get_class($e).'): '.$e->getMessage(), $e->getCode(), $e);
         }
     }
 
     private function health_check()
     {
-        if ($this->server->isSwarm()) {
-            // Implement healthcheck for swarm
-        } else {
-            if ($this->application->isHealthcheckDisabled() && $this->application->custom_healthcheck_found === false) {
-                $this->newVersionIsHealthy = true;
+        try {
+            if ($this->server->isSwarm()) {
+                // Implement healthcheck for swarm
+            } else {
+                if ($this->application->isHealthcheckDisabled() && $this->application->custom_healthcheck_found === false) {
+                    $this->newVersionIsHealthy = true;
 
-                return;
-            }
-            if ($this->application->custom_healthcheck_found) {
-                $this->application_deployment_queue->addLogEntry('Custom healthcheck found in Dockerfile.');
-            }
-            if ($this->container_name) {
-                $counter = 1;
-                $this->application_deployment_queue->addLogEntry('Waiting for healthcheck to pass on the new container.');
-                if ($this->full_healthcheck_url && ! $this->application->custom_healthcheck_found) {
-                    $this->application_deployment_queue->addLogEntry("Healthcheck URL (inside the container): {$this->full_healthcheck_url}");
+                    return;
                 }
-                $this->application_deployment_queue->addLogEntry("Waiting for the start period ({$this->application->health_check_start_period} seconds) before starting healthcheck.");
-                $sleeptime = 0;
-                while ($sleeptime < $this->application->health_check_start_period) {
-                    Sleep::for(1)->seconds();
-                    $sleeptime++;
+                if ($this->application->custom_healthcheck_found) {
+                    $this->application_deployment_queue->addLogEntry('Custom healthcheck found in Dockerfile.');
                 }
-                while ($counter <= $this->application->health_check_retries) {
-                    $this->execute_remote_command(
-                        [
-                            "docker inspect --format='{{json .State.Health.Status}}' {$this->container_name}",
-                            'hidden' => true,
-                            'save' => 'health_check',
-                            'append' => false,
-                        ],
-                        [
-                            "docker inspect --format='{{json .State.Health.Log}}' {$this->container_name}",
-                            'hidden' => true,
-                            'save' => 'health_check_logs',
-                            'append' => false,
-                        ],
-                    );
-                    $this->application_deployment_queue->addLogEntry("Attempt {$counter} of {$this->application->health_check_retries} | Healthcheck status: {$this->saved_outputs->get('health_check')}");
-                    $health_check_logs = data_get(collect(json_decode($this->saved_outputs->get('health_check_logs')))->last(), 'Output', '(no logs)');
-                    if (empty($health_check_logs)) {
-                        $health_check_logs = '(no logs)';
+                if ($this->container_name) {
+                    $counter = 1;
+                    $this->application_deployment_queue->addLogEntry('Waiting for healthcheck to pass on the new container.');
+                    if ($this->full_healthcheck_url && ! $this->application->custom_healthcheck_found) {
+                        $this->application_deployment_queue->addLogEntry("Healthcheck URL (inside the container): {$this->full_healthcheck_url}");
                     }
-                    $health_check_return_code = data_get(collect(json_decode($this->saved_outputs->get('health_check_logs')))->last(), 'ExitCode', '(no return code)');
-                    if ($health_check_logs !== '(no logs)' || $health_check_return_code !== '(no return code)') {
-                        $this->application_deployment_queue->addLogEntry("Healthcheck logs: {$health_check_logs} | Return code: {$health_check_return_code}");
-                    }
-
-                    if (str($this->saved_outputs->get('health_check'))->replace('"', '')->value() === 'healthy') {
-                        $this->newVersionIsHealthy = true;
-                        $this->application->update(['status' => 'running']);
-                        $this->application_deployment_queue->addLogEntry('New container is healthy.');
-                        break;
-                    }
-                    if (str($this->saved_outputs->get('health_check'))->replace('"', '')->value() === 'unhealthy') {
-                        $this->newVersionIsHealthy = false;
-                        $this->query_logs();
-                        break;
-                    }
-                    $counter++;
+                    $this->application_deployment_queue->addLogEntry("Waiting for the start period ({$this->application->health_check_start_period} seconds) before starting healthcheck.");
                     $sleeptime = 0;
-                    while ($sleeptime < $this->application->health_check_interval) {
+                    while ($sleeptime < $this->application->health_check_start_period) {
                         Sleep::for(1)->seconds();
                         $sleeptime++;
                     }
-                }
-                if (str($this->saved_outputs->get('health_check'))->replace('"', '')->value() === 'starting') {
-                    $this->query_logs();
+                    while ($counter <= $this->application->health_check_retries) {
+                        $this->execute_remote_command(
+                            [
+                                "docker inspect --format='{{json .State.Health.Status}}' {$this->container_name}",
+                                'hidden' => true,
+                                'save' => 'health_check',
+                                'append' => false,
+                            ],
+                            [
+                                "docker inspect --format='{{json .State.Health.Log}}' {$this->container_name}",
+                                'hidden' => true,
+                                'save' => 'health_check_logs',
+                                'append' => false,
+                            ],
+                        );
+                        $this->application_deployment_queue->addLogEntry("Attempt {$counter} of {$this->application->health_check_retries} | Healthcheck status: {$this->saved_outputs->get('health_check')}");
+                        $health_check_logs = data_get(collect(json_decode($this->saved_outputs->get('health_check_logs')))->last(), 'Output', '(no logs)');
+                        if (empty($health_check_logs)) {
+                            $health_check_logs = '(no logs)';
+                        }
+                        $health_check_return_code = data_get(collect(json_decode($this->saved_outputs->get('health_check_logs')))->last(), 'ExitCode', '(no return code)');
+                        if ($health_check_logs !== '(no logs)' || $health_check_return_code !== '(no return code)') {
+                            $this->application_deployment_queue->addLogEntry("Healthcheck logs: {$health_check_logs} | Return code: {$health_check_return_code}");
+                        }
+
+                        if (str($this->saved_outputs->get('health_check'))->replace('"', '')->value() === 'healthy') {
+                            $this->newVersionIsHealthy = true;
+                            $this->application->update(['status' => 'running']);
+                            $this->application_deployment_queue->addLogEntry('New container is healthy.');
+                            break;
+                        }
+                        if (str($this->saved_outputs->get('health_check'))->replace('"', '')->value() === 'unhealthy') {
+                            $this->newVersionIsHealthy = false;
+                            $this->query_logs();
+                            break;
+                        }
+                        $counter++;
+                        $sleeptime = 0;
+                        while ($sleeptime < $this->application->health_check_interval) {
+                            Sleep::for(1)->seconds();
+                            $sleeptime++;
+                        }
+                    }
+                    if (str($this->saved_outputs->get('health_check'))->replace('"', '')->value() === 'starting') {
+                        $this->query_logs();
+                    }
                 }
             }
+        } catch (Exception $e) {
+            throw new DeploymentException('Health check failed ('.get_class($e).'): '.$e->getMessage(), $e->getCode(), $e);
         }
     }
 
@@ -3034,58 +3042,66 @@ private function graceful_shutdown_container(string $containerName)
 
     private function stop_running_container(bool $force = false)
     {
-        $this->application_deployment_queue->addLogEntry('Removing old containers.');
-        if ($this->newVersionIsHealthy || $force) {
-            if ($this->application->settings->is_consistent_container_name_enabled || str($this->application->settings->custom_internal_name)->isNotEmpty()) {
-                $this->graceful_shutdown_container($this->container_name);
-            } else {
-                $containers = getCurrentApplicationContainerStatus($this->server, $this->application->id, $this->pull_request_id);
-                if ($this->pull_request_id === 0) {
-                    $containers = $containers->filter(function ($container) {
-                        return data_get($container, 'Names') !== $this->container_name && data_get($container, 'Names') !== addPreviewDeploymentSuffix($this->container_name, $this->pull_request_id);
+        try {
+            $this->application_deployment_queue->addLogEntry('Removing old containers.');
+            if ($this->newVersionIsHealthy || $force) {
+                if ($this->application->settings->is_consistent_container_name_enabled || str($this->application->settings->custom_internal_name)->isNotEmpty()) {
+                    $this->graceful_shutdown_container($this->container_name);
+                } else {
+                    $containers = getCurrentApplicationContainerStatus($this->server, $this->application->id, $this->pull_request_id);
+                    if ($this->pull_request_id === 0) {
+                        $containers = $containers->filter(function ($container) {
+                            return data_get($container, 'Names') !== $this->container_name && data_get($container, 'Names') !== addPreviewDeploymentSuffix($this->container_name, $this->pull_request_id);
+                        });
+                    }
+                    $containers->each(function ($container) {
+                        $this->graceful_shutdown_container(data_get($container, 'Names'));
                     });
                 }
-                $containers->each(function ($container) {
-                    $this->graceful_shutdown_container(data_get($container, 'Names'));
-                });
+            } else {
+                if ($this->application->dockerfile || $this->application->build_pack === 'dockerfile' || $this->application->build_pack === 'dockerimage') {
+                    $this->application_deployment_queue->addLogEntry('----------------------------------------');
+                    $this->application_deployment_queue->addLogEntry("WARNING: Dockerfile or Docker Image based deployment detected. The healthcheck needs a curl or wget command to check the health of the application. Please make sure that it is available in the image or turn off healthcheck on Coolify's UI.");
+                    $this->application_deployment_queue->addLogEntry('----------------------------------------');
+                }
+                $this->application_deployment_queue->addLogEntry('New container is not healthy, rolling back to the old container.');
+                $this->failDeployment();
+                $this->graceful_shutdown_container($this->container_name);
             }
-        } else {
-            if ($this->application->dockerfile || $this->application->build_pack === 'dockerfile' || $this->application->build_pack === 'dockerimage') {
-                $this->application_deployment_queue->addLogEntry('----------------------------------------');
-                $this->application_deployment_queue->addLogEntry("WARNING: Dockerfile or Docker Image based deployment detected. The healthcheck needs a curl or wget command to check the health of the application. Please make sure that it is available in the image or turn off healthcheck on Coolify's UI.");
-                $this->application_deployment_queue->addLogEntry('----------------------------------------');
-            }
-            $this->application_deployment_queue->addLogEntry('New container is not healthy, rolling back to the old container.');
-            $this->failDeployment();
-            $this->graceful_shutdown_container($this->container_name);
+        } catch (Exception $e) {
+            throw new DeploymentException("Failed to stop running container: {$e->getMessage()}", $e->getCode(), $e);
         }
     }
 
     private function start_by_compose_file()
     {
-        // Ensure .env file exists before docker compose tries to load it (defensive programming)
-        $this->execute_remote_command(
-            ["touch {$this->configuration_dir}/.env", 'hidden' => true],
-        );
-
-        if ($this->application->build_pack === 'dockerimage') {
-            $this->application_deployment_queue->addLogEntry('Pulling latest images from the registry.');
+        try {
+            // Ensure .env file exists before docker compose tries to load it (defensive programming)
             $this->execute_remote_command(
-                [executeInDocker($this->deployment_uuid, "docker compose --project-name {$this->application->uuid} --project-directory {$this->workdir} pull"), 'hidden' => true],
-                [executeInDocker($this->deployment_uuid, "{$this->coolify_variables} docker compose --project-name {$this->application->uuid} --project-directory {$this->workdir} up --build -d"), 'hidden' => true],
+                ["touch {$this->configuration_dir}/.env", 'hidden' => true],
             );
-        } else {
-            if ($this->use_build_server) {
+
+            if ($this->application->build_pack === 'dockerimage') {
+                $this->application_deployment_queue->addLogEntry('Pulling latest images from the registry.');
                 $this->execute_remote_command(
-                    ["{$this->coolify_variables} docker compose --project-name {$this->application->uuid} --project-directory {$this->configuration_dir} -f {$this->configuration_dir}{$this->docker_compose_location} up --pull always --build -d", 'hidden' => true],
+                    [executeInDocker($this->deployment_uuid, "docker compose --project-name {$this->application->uuid} --project-directory {$this->workdir} pull"), 'hidden' => true],
+                    [executeInDocker($this->deployment_uuid, "{$this->coolify_variables} docker compose --project-name {$this->application->uuid} --project-directory {$this->workdir} up --build -d"), 'hidden' => true],
                 );
             } else {
-                $this->execute_remote_command(
-                    [executeInDocker($this->deployment_uuid, "{$this->coolify_variables} docker compose --project-name {$this->application->uuid} --project-directory {$this->workdir} -f {$this->workdir}{$this->docker_compose_location} up --build -d"), 'hidden' => true],
-                );
+                if ($this->use_build_server) {
+                    $this->execute_remote_command(
+                        ["{$this->coolify_variables} docker compose --project-name {$this->application->uuid} --project-directory {$this->configuration_dir} -f {$this->configuration_dir}{$this->docker_compose_location} up --pull always --build -d", 'hidden' => true],
+                    );
+                } else {
+                    $this->execute_remote_command(
+                        [executeInDocker($this->deployment_uuid, "{$this->coolify_variables} docker compose --project-name {$this->application->uuid} --project-directory {$this->workdir} -f {$this->workdir}{$this->docker_compose_location} up --build -d"), 'hidden' => true],
+                    );
+                }
             }
+            $this->application_deployment_queue->addLogEntry('New container started.');
+        } catch (Exception $e) {
+            throw new DeploymentException("Failed to start container: {$e->getMessage()}", $e->getCode(), $e);
         }
-        $this->application_deployment_queue->addLogEntry('New container started.');
     }
 
     private function analyzeBuildTimeVariables($variables)
@@ -3829,7 +3845,7 @@ private function completeDeployment(): void
      * Fail the deployment.
      * Sends failure notification and queues next deployment.
      */
-    private function failDeployment(): void
+    protected function failDeployment(): void
     {
         $this->transitionToStatus(ApplicationDeploymentStatus::FAILED);
     }
@@ -3837,8 +3853,38 @@ private function failDeployment(): void
     public function failed(Throwable $exception): void
     {
         $this->failDeployment();
+
+        // Log comprehensive error information
         $errorMessage = $exception->getMessage() ?: 'Unknown error occurred';
+        $errorCode = $exception->getCode();
+        $errorClass = get_class($exception);
+
+        $this->application_deployment_queue->addLogEntry('========================================', 'stderr');
         $this->application_deployment_queue->addLogEntry("Deployment failed: {$errorMessage}", 'stderr');
+        $this->application_deployment_queue->addLogEntry("Error type: {$errorClass}", 'stderr', hidden: true);
+        $this->application_deployment_queue->addLogEntry("Error code: {$errorCode}", 'stderr', hidden: true);
+
+        // Log the exception file and line for debugging
+        $this->application_deployment_queue->addLogEntry("Location: {$exception->getFile()}:{$exception->getLine()}", 'stderr', hidden: true);
+
+        // Log previous exceptions if they exist (for chained exceptions)
+        $previous = $exception->getPrevious();
+        if ($previous) {
+            $this->application_deployment_queue->addLogEntry('Caused by:', 'stderr', hidden: true);
+            $previousMessage = $previous->getMessage() ?: 'No message';
+            $previousClass = get_class($previous);
+            $this->application_deployment_queue->addLogEntry("  {$previousClass}: {$previousMessage}", 'stderr', hidden: true);
+            $this->application_deployment_queue->addLogEntry("  at {$previous->getFile()}:{$previous->getLine()}", 'stderr', hidden: true);
+        }
+
+        // Log first few lines of stack trace for debugging
+        $trace = $exception->getTraceAsString();
+        $traceLines = explode("\n", $trace);
+        $this->application_deployment_queue->addLogEntry('Stack trace (first 5 lines):', 'stderr', hidden: true);
+        foreach (array_slice($traceLines, 0, 5) as $traceLine) {
+            $this->application_deployment_queue->addLogEntry("  {$traceLine}", 'stderr', hidden: true);
+        }
+        $this->application_deployment_queue->addLogEntry('========================================', 'stderr');
 
         if ($this->application->build_pack !== 'dockercompose') {
             $code = $exception->getCode();
diff --git a/app/Jobs/ServerManagerJob.php b/app/Jobs/ServerManagerJob.php
index 043845c00..45ab1dde8 100644
--- a/app/Jobs/ServerManagerJob.php
+++ b/app/Jobs/ServerManagerJob.php
@@ -87,7 +87,7 @@ private function dispatchConnectionChecks(Collection $servers): void
                     Log::channel('scheduled-errors')->error('Failed to dispatch ServerConnectionCheck', [
                         'server_id' => $server->id,
                         'server_name' => $server->name,
-                        'error' => $e->getMessage(),
+                        'error' => get_class($e).': '.$e->getMessage(),
                     ]);
                 }
             });
@@ -103,7 +103,7 @@ private function processScheduledTasks(Collection $servers): void
                 Log::channel('scheduled-errors')->error('Error processing server tasks', [
                     'server_id' => $server->id,
                     'server_name' => $server->name,
-                    'error' => $e->getMessage(),
+                    'error' => get_class($e).': '.$e->getMessage(),
                 ]);
             }
         }
diff --git a/tests/Unit/ApplicationDeploymentErrorLoggingTest.php b/tests/Unit/ApplicationDeploymentErrorLoggingTest.php
new file mode 100644
index 000000000..c6210639a
--- /dev/null
+++ b/tests/Unit/ApplicationDeploymentErrorLoggingTest.php
@@ -0,0 +1,344 @@
+<?php
+
+use App\Exceptions\DeploymentException;
+use App\Jobs\ApplicationDeploymentJob;
+use App\Models\Application;
+use App\Models\ApplicationDeploymentQueue;
+
+/**
+ * Test to verify that deployment errors are properly logged with comprehensive details.
+ *
+ * This test suite verifies the fix for issue #7113 where deployments fail without
+ * clear error messages. The fix ensures that all deployment failures log:
+ * - The exception message
+ * - The exception type/class
+ * - The exception code (if present)
+ * - The file and line where the error occurred
+ * - Previous exception details (if chained)
+ * - Stack trace (first 5 lines)
+ */
+it('logs comprehensive error details when failed() is called', function () {
+    // Create a mock exception with all properties
+    $innerException = new \RuntimeException('Connection refused', 111);
+    $exception = new DeploymentException(
+        'Failed to start container',
+        500,
+        $innerException
+    );
+
+    // Mock the application deployment queue
+    $mockQueue = Mockery::mock(ApplicationDeploymentQueue::class);
+    $logEntries = [];
+
+    // Capture all log entries
+    $mockQueue->shouldReceive('addLogEntry')
+        ->withArgs(function ($message, $type = 'stdout', $hidden = false) use (&$logEntries) {
+            $logEntries[] = ['message' => $message, 'type' => $type, 'hidden' => $hidden];
+
+            return true;
+        })
+        ->atLeast()->once();
+
+    $mockQueue->shouldReceive('update')->andReturn(true);
+
+    // Mock Application and its relationships
+    $mockApplication = Mockery::mock(Application::class);
+    $mockApplication->shouldReceive('getAttribute')
+        ->with('build_pack')
+        ->andReturn('dockerfile');
+    $mockApplication->shouldReceive('setAttribute')
+        ->with('build_pack', 'dockerfile')
+        ->andReturnSelf();
+    $mockApplication->build_pack = 'dockerfile';
+
+    $mockSettings = Mockery::mock();
+    $mockSettings->shouldReceive('getAttribute')
+        ->with('is_consistent_container_name_enabled')
+        ->andReturn(false);
+    $mockSettings->shouldReceive('getAttribute')
+        ->with('custom_internal_name')
+        ->andReturn('');
+    $mockSettings->shouldReceive('setAttribute')
+        ->andReturnSelf();
+    $mockSettings->is_consistent_container_name_enabled = false;
+    $mockSettings->custom_internal_name = '';
+
+    $mockApplication->shouldReceive('getAttribute')
+        ->with('settings')
+        ->andReturn($mockSettings);
+
+    // Use reflection to set private properties and call the failed() method
+    $job = Mockery::mock(ApplicationDeploymentJob::class)->makePartial();
+    $job->shouldAllowMockingProtectedMethods();
+
+    $reflection = new \ReflectionClass(ApplicationDeploymentJob::class);
+
+    $queueProperty = $reflection->getProperty('application_deployment_queue');
+    $queueProperty->setAccessible(true);
+    $queueProperty->setValue($job, $mockQueue);
+
+    $applicationProperty = $reflection->getProperty('application');
+    $applicationProperty->setAccessible(true);
+    $applicationProperty->setValue($job, $mockApplication);
+
+    $pullRequestProperty = $reflection->getProperty('pull_request_id');
+    $pullRequestProperty->setAccessible(true);
+    $pullRequestProperty->setValue($job, 0);
+
+    $containerNameProperty = $reflection->getProperty('container_name');
+    $containerNameProperty->setAccessible(true);
+    $containerNameProperty->setValue($job, 'test-container');
+
+    // Mock the failDeployment method to prevent errors
+    $job->shouldReceive('failDeployment')->andReturn();
+    $job->shouldReceive('execute_remote_command')->andReturn();
+
+    // Call the failed method
+    $failedMethod = $reflection->getMethod('failed');
+    $failedMethod->setAccessible(true);
+    $failedMethod->invoke($job, $exception);
+
+    // Verify comprehensive error logging
+    $errorMessages = array_column($logEntries, 'message');
+    $errorMessageString = implode("\n", $errorMessages);
+
+    // Check that all critical information is logged
+    expect($errorMessageString)->toContain('Deployment failed: Failed to start container');
+    expect($errorMessageString)->toContain('Error type: App\Exceptions\DeploymentException');
+    expect($errorMessageString)->toContain('Error code: 500');
+    expect($errorMessageString)->toContain('Location:');
+    expect($errorMessageString)->toContain('Caused by:');
+    expect($errorMessageString)->toContain('RuntimeException: Connection refused');
+    expect($errorMessageString)->toContain('Stack trace');
+
+    // Verify stderr type is used for error logging
+    $stderrEntries = array_filter($logEntries, fn ($entry) => $entry['type'] === 'stderr');
+    expect(count($stderrEntries))->toBeGreaterThan(0);
+
+    // Verify that the main error message is NOT hidden
+    $mainErrorEntry = collect($logEntries)->first(fn ($entry) => str_contains($entry['message'], 'Deployment failed: Failed to start container'));
+    expect($mainErrorEntry['hidden'])->toBeFalse();
+
+    // Verify that technical details ARE hidden
+    $errorTypeEntry = collect($logEntries)->first(fn ($entry) => str_contains($entry['message'], 'Error type:'));
+    expect($errorTypeEntry['hidden'])->toBeTrue();
+
+    $errorCodeEntry = collect($logEntries)->first(fn ($entry) => str_contains($entry['message'], 'Error code:'));
+    expect($errorCodeEntry['hidden'])->toBeTrue();
+
+    $locationEntry = collect($logEntries)->first(fn ($entry) => str_contains($entry['message'], 'Location:'));
+    expect($locationEntry['hidden'])->toBeTrue();
+
+    $stackTraceEntry = collect($logEntries)->first(fn ($entry) => str_contains($entry['message'], 'Stack trace'));
+    expect($stackTraceEntry['hidden'])->toBeTrue();
+
+    $causedByEntry = collect($logEntries)->first(fn ($entry) => str_contains($entry['message'], 'Caused by:'));
+    expect($causedByEntry['hidden'])->toBeTrue();
+});
+
+it('handles exceptions with no message gracefully', function () {
+    $exception = new \Exception;
+
+    $mockQueue = Mockery::mock(ApplicationDeploymentQueue::class);
+    $logEntries = [];
+
+    $mockQueue->shouldReceive('addLogEntry')
+        ->withArgs(function ($message, $type = 'stdout', $hidden = false) use (&$logEntries) {
+            $logEntries[] = ['message' => $message, 'type' => $type, 'hidden' => $hidden];
+
+            return true;
+        })
+        ->atLeast()->once();
+
+    $mockQueue->shouldReceive('update')->andReturn(true);
+
+    $mockApplication = Mockery::mock(Application::class);
+    $mockApplication->shouldReceive('getAttribute')
+        ->with('build_pack')
+        ->andReturn('dockerfile');
+    $mockApplication->shouldReceive('setAttribute')
+        ->with('build_pack', 'dockerfile')
+        ->andReturnSelf();
+    $mockApplication->build_pack = 'dockerfile';
+
+    $mockSettings = Mockery::mock();
+    $mockSettings->shouldReceive('getAttribute')
+        ->with('is_consistent_container_name_enabled')
+        ->andReturn(false);
+    $mockSettings->shouldReceive('getAttribute')
+        ->with('custom_internal_name')
+        ->andReturn('');
+    $mockSettings->shouldReceive('setAttribute')
+        ->andReturnSelf();
+    $mockSettings->is_consistent_container_name_enabled = false;
+    $mockSettings->custom_internal_name = '';
+
+    $mockApplication->shouldReceive('getAttribute')
+        ->with('settings')
+        ->andReturn($mockSettings);
+
+    $job = Mockery::mock(ApplicationDeploymentJob::class)->makePartial();
+    $job->shouldAllowMockingProtectedMethods();
+
+    $reflection = new \ReflectionClass(ApplicationDeploymentJob::class);
+
+    $queueProperty = $reflection->getProperty('application_deployment_queue');
+    $queueProperty->setAccessible(true);
+    $queueProperty->setValue($job, $mockQueue);
+
+    $applicationProperty = $reflection->getProperty('application');
+    $applicationProperty->setAccessible(true);
+    $applicationProperty->setValue($job, $mockApplication);
+
+    $pullRequestProperty = $reflection->getProperty('pull_request_id');
+    $pullRequestProperty->setAccessible(true);
+    $pullRequestProperty->setValue($job, 0);
+
+    $containerNameProperty = $reflection->getProperty('container_name');
+    $containerNameProperty->setAccessible(true);
+    $containerNameProperty->setValue($job, 'test-container');
+
+    $job->shouldReceive('failDeployment')->andReturn();
+    $job->shouldReceive('execute_remote_command')->andReturn();
+
+    $failedMethod = $reflection->getMethod('failed');
+    $failedMethod->setAccessible(true);
+    $failedMethod->invoke($job, $exception);
+
+    $errorMessages = array_column($logEntries, 'message');
+    $errorMessageString = implode("\n", $errorMessages);
+
+    // Should log "Unknown error occurred" for empty messages
+    expect($errorMessageString)->toContain('Unknown error occurred');
+    expect($errorMessageString)->toContain('Error type:');
+});
+
+it('wraps exceptions in deployment methods with DeploymentException', function () {
+    // Verify that our deployment methods wrap exceptions properly
+    $originalException = new \RuntimeException('Container not found');
+
+    try {
+        throw new DeploymentException('Failed to start container', 0, $originalException);
+    } catch (DeploymentException $e) {
+        expect($e->getMessage())->toBe('Failed to start container');
+        expect($e->getPrevious())->toBe($originalException);
+        expect($e->getPrevious()->getMessage())->toBe('Container not found');
+    }
+});
+
+it('logs error code 0 correctly', function () {
+    // Verify that error code 0 is logged (previously skipped due to falsy check)
+    $exception = new \Exception('Test error', 0);
+
+    $mockQueue = Mockery::mock(ApplicationDeploymentQueue::class);
+    $logEntries = [];
+
+    $mockQueue->shouldReceive('addLogEntry')
+        ->withArgs(function ($message, $type = 'stdout', $hidden = false) use (&$logEntries) {
+            $logEntries[] = ['message' => $message, 'type' => $type, 'hidden' => $hidden];
+
+            return true;
+        })
+        ->atLeast()->once();
+
+    $mockQueue->shouldReceive('update')->andReturn(true);
+
+    $mockApplication = Mockery::mock(Application::class);
+    $mockApplication->shouldReceive('getAttribute')
+        ->with('build_pack')
+        ->andReturn('dockerfile');
+    $mockApplication->shouldReceive('setAttribute')
+        ->with('build_pack', 'dockerfile')
+        ->andReturnSelf();
+    $mockApplication->build_pack = 'dockerfile';
+
+    $mockSettings = Mockery::mock();
+    $mockSettings->shouldReceive('getAttribute')
+        ->with('is_consistent_container_name_enabled')
+        ->andReturn(false);
+    $mockSettings->shouldReceive('getAttribute')
+        ->with('custom_internal_name')
+        ->andReturn('');
+    $mockSettings->shouldReceive('setAttribute')
+        ->andReturnSelf();
+    $mockSettings->is_consistent_container_name_enabled = false;
+    $mockSettings->custom_internal_name = '';
+
+    $mockApplication->shouldReceive('getAttribute')
+        ->with('settings')
+        ->andReturn($mockSettings);
+
+    $job = Mockery::mock(ApplicationDeploymentJob::class)->makePartial();
+    $job->shouldAllowMockingProtectedMethods();
+
+    $reflection = new \ReflectionClass(ApplicationDeploymentJob::class);
+
+    $queueProperty = $reflection->getProperty('application_deployment_queue');
+    $queueProperty->setAccessible(true);
+    $queueProperty->setValue($job, $mockQueue);
+
+    $applicationProperty = $reflection->getProperty('application');
+    $applicationProperty->setAccessible(true);
+    $applicationProperty->setValue($job, $mockApplication);
+
+    $pullRequestProperty = $reflection->getProperty('pull_request_id');
+    $pullRequestProperty->setAccessible(true);
+    $pullRequestProperty->setValue($job, 0);
+
+    $containerNameProperty = $reflection->getProperty('container_name');
+    $containerNameProperty->setAccessible(true);
+    $containerNameProperty->setValue($job, 'test-container');
+
+    $job->shouldReceive('failDeployment')->andReturn();
+    $job->shouldReceive('execute_remote_command')->andReturn();
+
+    $failedMethod = $reflection->getMethod('failed');
+    $failedMethod->setAccessible(true);
+    $failedMethod->invoke($job, $exception);
+
+    $errorMessages = array_column($logEntries, 'message');
+    $errorMessageString = implode("\n", $errorMessages);
+
+    // Should log error code 0 (not skip it)
+    expect($errorMessageString)->toContain('Error code: 0');
+});
+
+it('preserves original exception type in wrapped DeploymentException messages', function () {
+    // Verify that when wrapping exceptions, the original exception type is included in the message
+    $originalException = new \RuntimeException('Connection timeout');
+
+    // Test rolling update scenario
+    $wrappedException = new DeploymentException(
+        'Rolling update failed ('.get_class($originalException).'): '.$originalException->getMessage(),
+        $originalException->getCode(),
+        $originalException
+    );
+
+    expect($wrappedException->getMessage())->toContain('RuntimeException');
+    expect($wrappedException->getMessage())->toContain('Connection timeout');
+    expect($wrappedException->getPrevious())->toBe($originalException);
+
+    // Test health check scenario
+    $healthCheckException = new \InvalidArgumentException('Invalid health check URL');
+    $wrappedHealthCheck = new DeploymentException(
+        'Health check failed ('.get_class($healthCheckException).'): '.$healthCheckException->getMessage(),
+        $healthCheckException->getCode(),
+        $healthCheckException
+    );
+
+    expect($wrappedHealthCheck->getMessage())->toContain('InvalidArgumentException');
+    expect($wrappedHealthCheck->getMessage())->toContain('Invalid health check URL');
+    expect($wrappedHealthCheck->getPrevious())->toBe($healthCheckException);
+
+    // Test docker registry push scenario
+    $registryException = new \RuntimeException('Failed to authenticate');
+    $wrappedRegistry = new DeploymentException(
+        get_class($registryException).': '.$registryException->getMessage(),
+        $registryException->getCode(),
+        $registryException
+    );
+
+    expect($wrappedRegistry->getMessage())->toContain('RuntimeException');
+    expect($wrappedRegistry->getMessage())->toContain('Failed to authenticate');
+    expect($wrappedRegistry->getPrevious())->toBe($registryException);
+});