diff --git a/app/Jobs/ApplicationDeploymentJob.php b/app/Jobs/ApplicationDeploymentJob.php
index 9721d8267..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);
             }
         }
     }
@@ -1655,7 +1655,7 @@ private function rolling_update()
                 }
             }
         } catch (Exception $e) {
-            throw new DeploymentException("Rolling update failed: {$e->getMessage()}", $e->getCode(), $e);
+            throw new DeploymentException('Rolling update failed ('.get_class($e).'): '.$e->getMessage(), $e->getCode(), $e);
         }
     }
 
@@ -1734,8 +1734,7 @@ private function health_check()
                 }
             }
         } catch (Exception $e) {
-            $this->newVersionIsHealthy = false;
-            throw new DeploymentException("Health check failed: {$e->getMessage()}", $e->getCode(), $e);
+            throw new DeploymentException('Health check failed ('.get_class($e).'): '.$e->getMessage(), $e->getCode(), $e);
         }
     }
 
@@ -3846,7 +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);
     }
@@ -3862,28 +3861,28 @@ public function failed(Throwable $exception): void
 
         $this->application_deployment_queue->addLogEntry('========================================', 'stderr');
         $this->application_deployment_queue->addLogEntry("Deployment failed: {$errorMessage}", 'stderr');
-        $this->application_deployment_queue->addLogEntry("Error type: {$errorClass}", 'stderr');
-        $this->application_deployment_queue->addLogEntry("Error code: {$errorCode}", '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');
+        $this->application_deployment_queue->addLogEntry("Location: {$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');
+            $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');
-            $this->application_deployment_queue->addLogEntry("  at {$previous->getFile()}:{$previous->getLine()}", 'stderr');
+            $this->application_deployment_queue->addLogEntry("  {$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');
+        $this->application_deployment_queue->addLogEntry('Stack trace (first 5 lines):', 'stderr', hidden: true);
         foreach (array_slice($traceLines, 0, 5) as $traceLine) {
-            $this->application_deployment_queue->addLogEntry("  {$traceLine}", 'stderr');
+            $this->application_deployment_queue->addLogEntry("  {$traceLine}", 'stderr', hidden: true);
         }
         $this->application_deployment_queue->addLogEntry('========================================', 'stderr');
 
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
index b2557c4f3..c6210639a 100644
--- a/tests/Unit/ApplicationDeploymentErrorLoggingTest.php
+++ b/tests/Unit/ApplicationDeploymentErrorLoggingTest.php
@@ -4,7 +4,6 @@
 use App\Jobs\ApplicationDeploymentJob;
 use App\Models\Application;
 use App\Models\ApplicationDeploymentQueue;
-use Mockery;
 
 /**
  * Test to verify that deployment errors are properly logged with comprehensive details.
@@ -33,8 +32,8 @@
 
     // Capture all log entries
     $mockQueue->shouldReceive('addLogEntry')
-        ->withArgs(function ($message, $type = 'stdout') use (&$logEntries) {
-            $logEntries[] = ['message' => $message, 'type' => $type];
+        ->withArgs(function ($message, $type = 'stdout', $hidden = false) use (&$logEntries) {
+            $logEntries[] = ['message' => $message, 'type' => $type, 'hidden' => $hidden];
 
             return true;
         })
@@ -47,6 +46,9 @@
     $mockApplication->shouldReceive('getAttribute')
         ->with('build_pack')
         ->andReturn('dockerfile');
+    $mockApplication->shouldReceive('setAttribute')
+        ->with('build_pack', 'dockerfile')
+        ->andReturnSelf();
     $mockApplication->build_pack = 'dockerfile';
 
     $mockSettings = Mockery::mock();
@@ -56,6 +58,8 @@
     $mockSettings->shouldReceive('getAttribute')
         ->with('custom_internal_name')
         ->andReturn('');
+    $mockSettings->shouldReceive('setAttribute')
+        ->andReturnSelf();
     $mockSettings->is_consistent_container_name_enabled = false;
     $mockSettings->custom_internal_name = '';
 
@@ -67,7 +71,7 @@
     $job = Mockery::mock(ApplicationDeploymentJob::class)->makePartial();
     $job->shouldAllowMockingProtectedMethods();
 
-    $reflection = new \ReflectionClass($job);
+    $reflection = new \ReflectionClass(ApplicationDeploymentJob::class);
 
     $queueProperty = $reflection->getProperty('application_deployment_queue');
     $queueProperty->setAccessible(true);
@@ -81,6 +85,10 @@
     $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();
@@ -106,6 +114,26 @@
     // 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 () {
@@ -115,8 +143,8 @@
     $logEntries = [];
 
     $mockQueue->shouldReceive('addLogEntry')
-        ->withArgs(function ($message, $type = 'stdout') use (&$logEntries) {
-            $logEntries[] = ['message' => $message, 'type' => $type];
+        ->withArgs(function ($message, $type = 'stdout', $hidden = false) use (&$logEntries) {
+            $logEntries[] = ['message' => $message, 'type' => $type, 'hidden' => $hidden];
 
             return true;
         })
@@ -128,6 +156,9 @@
     $mockApplication->shouldReceive('getAttribute')
         ->with('build_pack')
         ->andReturn('dockerfile');
+    $mockApplication->shouldReceive('setAttribute')
+        ->with('build_pack', 'dockerfile')
+        ->andReturnSelf();
     $mockApplication->build_pack = 'dockerfile';
 
     $mockSettings = Mockery::mock();
@@ -137,6 +168,8 @@
     $mockSettings->shouldReceive('getAttribute')
         ->with('custom_internal_name')
         ->andReturn('');
+    $mockSettings->shouldReceive('setAttribute')
+        ->andReturnSelf();
     $mockSettings->is_consistent_container_name_enabled = false;
     $mockSettings->custom_internal_name = '';
 
@@ -147,7 +180,7 @@
     $job = Mockery::mock(ApplicationDeploymentJob::class)->makePartial();
     $job->shouldAllowMockingProtectedMethods();
 
-    $reflection = new \ReflectionClass($job);
+    $reflection = new \ReflectionClass(ApplicationDeploymentJob::class);
 
     $queueProperty = $reflection->getProperty('application_deployment_queue');
     $queueProperty->setAccessible(true);
@@ -161,6 +194,10 @@
     $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();
 
@@ -197,8 +234,8 @@
     $logEntries = [];
 
     $mockQueue->shouldReceive('addLogEntry')
-        ->withArgs(function ($message, $type = 'stdout') use (&$logEntries) {
-            $logEntries[] = ['message' => $message, 'type' => $type];
+        ->withArgs(function ($message, $type = 'stdout', $hidden = false) use (&$logEntries) {
+            $logEntries[] = ['message' => $message, 'type' => $type, 'hidden' => $hidden];
 
             return true;
         })
@@ -210,6 +247,9 @@
     $mockApplication->shouldReceive('getAttribute')
         ->with('build_pack')
         ->andReturn('dockerfile');
+    $mockApplication->shouldReceive('setAttribute')
+        ->with('build_pack', 'dockerfile')
+        ->andReturnSelf();
     $mockApplication->build_pack = 'dockerfile';
 
     $mockSettings = Mockery::mock();
@@ -219,6 +259,8 @@
     $mockSettings->shouldReceive('getAttribute')
         ->with('custom_internal_name')
         ->andReturn('');
+    $mockSettings->shouldReceive('setAttribute')
+        ->andReturnSelf();
     $mockSettings->is_consistent_container_name_enabled = false;
     $mockSettings->custom_internal_name = '';
 
@@ -229,7 +271,7 @@
     $job = Mockery::mock(ApplicationDeploymentJob::class)->makePartial();
     $job->shouldAllowMockingProtectedMethods();
 
-    $reflection = new \ReflectionClass($job);
+    $reflection = new \ReflectionClass(ApplicationDeploymentJob::class);
 
     $queueProperty = $reflection->getProperty('application_deployment_queue');
     $queueProperty->setAccessible(true);
@@ -243,6 +285,10 @@
     $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();
 
@@ -256,3 +302,43 @@
     // 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);
+});