diff --git a/app/Jobs/Schedule/RunTaskJob.php b/app/Jobs/Schedule/RunTaskJob.php
index 8784a37cb..ee3c3e16d 100644
--- a/app/Jobs/Schedule/RunTaskJob.php
+++ b/app/Jobs/Schedule/RunTaskJob.php
@@ -69,7 +69,7 @@ class RunTaskJob extends Job implements ShouldQueue
                 $commandRepository->setServer($server)->send($this->task->payload);
                 break;
             case 'backup':
-                $backupService->setIgnoredFiles(explode(PHP_EOL, $this->task->payload))->handle($server, null);
+                $backupService->setIgnoredFiles(explode(PHP_EOL, $this->task->payload))->handle($server, null, true);
                 break;
             default:
                 throw new InvalidArgumentException('Cannot run a task that points to a non-existent action.');
diff --git a/app/Services/Backups/InitiateBackupService.php b/app/Services/Backups/InitiateBackupService.php
index ca8c3decd..9b6ae9a6f 100644
--- a/app/Services/Backups/InitiateBackupService.php
+++ b/app/Services/Backups/InitiateBackupService.php
@@ -13,6 +13,7 @@ use Pterodactyl\Repositories\Eloquent\BackupRepository;
 use Pterodactyl\Repositories\Wings\DaemonBackupRepository;
 use Pterodactyl\Exceptions\Service\Backup\TooManyBackupsException;
 use Symfony\Component\HttpKernel\Exception\TooManyRequestsHttpException;
+use Pterodactyl\Services\Backups\DeleteBackupService;
 
 class InitiateBackupService
 {
@@ -41,24 +42,32 @@ class InitiateBackupService
      */
     private $backupManager;
 
+    /**
+     * @var \Pterodactyl\Services\Backups\DeleteBackupService
+     */
+    private $deleteBackupService;
+
     /**
      * InitiateBackupService constructor.
      *
      * @param \Pterodactyl\Repositories\Eloquent\BackupRepository $repository
      * @param \Illuminate\Database\ConnectionInterface $connection
      * @param \Pterodactyl\Repositories\Wings\DaemonBackupRepository $daemonBackupRepository
+     * @param \Pterodactyl\Services\Backups\DeleteBackupService $deleteBackupService
      * @param \Pterodactyl\Extensions\Backups\BackupManager $backupManager
      */
     public function __construct(
         BackupRepository $repository,
         ConnectionInterface $connection,
         DaemonBackupRepository $daemonBackupRepository,
+        DeleteBackupService $deleteBackupService,
         BackupManager $backupManager
     ) {
         $this->repository = $repository;
         $this->connection = $connection;
         $this->daemonBackupRepository = $daemonBackupRepository;
         $this->backupManager = $backupManager;
+        $this->deleteBackupService = $deleteBackupService;
     }
 
     /**
@@ -96,13 +105,8 @@ class InitiateBackupService
      * @throws \Pterodactyl\Exceptions\Service\Backup\TooManyBackupsException
      * @throws \Symfony\Component\HttpKernel\Exception\TooManyRequestsHttpException
      */
-    public function handle(Server $server, string $name = null): Backup
+    public function handle(Server $server, string $name = null, bool $override = null): Backup
     {
-        // Do not allow the user to continue if this server is already at its limit.
-        if (! $server->backup_limit || $server->backups()->where('is_successful', true)->count() >= $server->backup_limit) {
-            throw new TooManyBackupsException($server->backup_limit);
-        }
-
         $previous = $this->repository->getBackupsGeneratedDuringTimespan($server->id, 10);
         if ($previous->count() >= 2) {
             throw new TooManyRequestsHttpException(
@@ -111,6 +115,17 @@ class InitiateBackupService
             );
         }
 
+        if (! $server->backup_limit || $server->backups()->where('is_successful', true)->count() >= $server->backup_limit) {
+            if($override){
+                // Remove latest backup
+                $last_backup = $server->backups()->where('is_successful', true)->oldest()->first();
+                $this->deleteBackupService->handle($last_backup);
+            }else{
+                // Do not allow the user to continue if this server is already at its limit.
+                throw new TooManyBackupsException($server->backup_limit);
+            }
+        }        
+
         return $this->connection->transaction(function () use ($server, $name) {
             /** @var \Pterodactyl\Models\Backup $backup */
             $backup = $this->repository->create([
@@ -121,9 +136,7 @@ class InitiateBackupService
                 'disk' => $this->backupManager->getDefaultAdapter(),
             ], true, true);
 
-            $this->daemonBackupRepository->setServer($server)
-                ->setBackupAdapter($this->backupManager->getDefaultAdapter())
-                ->backup($backup);
+            $this->daemonBackupRepository->setServer($server)->setBackupAdapter($this->backupManager->getDefaultAdapter())->backup($backup);
 
             return $backup;
         });
diff --git a/resources/scripts/components/server/schedules/TaskDetailsModal.tsx b/resources/scripts/components/server/schedules/TaskDetailsModal.tsx
index e1fca0cb0..5ff75555d 100644
--- a/resources/scripts/components/server/schedules/TaskDetailsModal.tsx
+++ b/resources/scripts/components/server/schedules/TaskDetailsModal.tsx
@@ -91,7 +91,7 @@ const TaskDetailsForm = ({ isEditingTask }: { isEditingTask: boolean }) => {
                             <Label>Ignored Files</Label>
                             <FormikFieldWrapper
                                 name={'payload'}
-                                description={'Optional. Include the files and folders to be excluded in this backup. By default, the contents of your .pteroignore file will be used.'}
+                                description={'Optional. Include the files and folders to be excluded in this backup. By default, the contents of your .pteroignore file will be used.\nIf you dont have more backups spaces it will OVERRIDE the oldest.'}
                             >
                                 <FormikField as={Textarea} name={'payload'} rows={6} />
                             </FormikFieldWrapper>