diff --git a/app/Services/Backups/InitiateBackupService.php b/app/Services/Backups/InitiateBackupService.php
index 3246328c9..aa53b88ae 100644
--- a/app/Services/Backups/InitiateBackupService.php
+++ b/app/Services/Backups/InitiateBackupService.php
@@ -116,16 +116,16 @@ 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() >= $server->backup_limit) {
-            if($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.
+        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 latest backup
+            $lastBackup = $server->backups()->where('is_successful', true)->orderByDesc('created_at')->first();
+            $this->deleteBackupService->handle($lastBackup);
+        }
 
         return $this->connection->transaction(function () use ($server, $name) {
             /** @var \Pterodactyl\Models\Backup $backup */
diff --git a/resources/scripts/components/server/schedules/TaskDetailsModal.tsx b/resources/scripts/components/server/schedules/TaskDetailsModal.tsx
index 65c647219..08f33b161 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.\nIf you have reached your backup limit, the oldest backup will be rotated.'}
+                                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>