Abstract: Embodiments of an envelope that is reusable and allows for efficient rerouting between intended recipients of the item in the envelope are disclosed. The envelope may be constructed of a durable material and may have various features that allow the envelope to be automatically sent via a carrier from one recipient to another. Thus, when a recipient of the item returns the envelope via the carrier, the envelope can be correctly processed and forwarded on to the next recipient with the same item, without the need of sending the item back to a return center or other entity. The term envelope generally includes envelopes, mailers and packages. Embodiments may include an envelope that facilitates multiple sorting and delivery cycles by the delivery service without the need for reconfiguration, repair, or replacement of the envelope.