diff --git a/app/Jobs/Schedule/RunTaskJob.php b/app/Jobs/Schedule/RunTaskJob.php
index 8784a37c..ee3c3e16 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 ca8c3dec..5c34961a 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 = false): 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 +115,18 @@ class InitiateBackupService
             );
         }
 
+        // Check if the server has reached or exceeded it's backup limit
+        if (!$server->backup_limit || $server->backups()->where('is_successful', true)->count() >= $server->backup_limit) {
+            // Do not allow the user to continue if this server is already at its limit and can't override.
+            if (!$override || $server->backup_limit <= 0) {
+                throw new TooManyBackupsException($server->backup_limit);
+            }
+
+            // Remove oldest backup
+            $oldestBackup = $server->backups()->where('is_successful', true)->orderByDesc('created_at')->first();
+            $this->deleteBackupService->handle($oldestBackup);
+        }
+
         return $this->connection->transaction(function () use ($server, $name) {
             /** @var \Pterodactyl\Models\Backup $backup */
             $backup = $this->repository->create([
diff --git a/resources/scripts/components/server/schedules/TaskDetailsModal.tsx b/resources/scripts/components/server/schedules/TaskDetailsModal.tsx
index e1fca0cb..08f33b16 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. If you have reached your backup limit, the oldest backup will be rotated.'}
                             >
                                 <FormikField as={Textarea} name={'payload'} rows={6} />
                             </FormikFieldWrapper>