When does a shipping label expire? | Pirate Ship Support It's important to remember that Pirate Ship will automatically refund you for any USPS or UPS label purchases that don't have tracking updates after 28 days 💰 By that point, you will want to recreate and repurchase it. Note that this only applies to any prepaid shipping labels! Our Pay-on-Use USPS Return Labels are valid for up to 90 days 😃