Various systems and methods are described for insertion of optional stops in delivery routes. To this end, a plurality of delivery routes is provided in a computing device, where each delivery route has a plurality of stops. A determination is made in the computing devices as to whether an optional stop can be inserted between a pair of the stops in at least one of the delivery routes without violating a predefined set of criteria. The optional stop is ultimately inserted between a respective pair of stops in a selected one of the delivery routes.