There is provided systems and methods for intelligent adjustment of shipping data based on past cubing tendencies. A user may access a service provider to request generation of shipping labels for one or more future packages to be shipped. The user may provide shipping data required to generate the labels, including a value for each label that is used to purchase shipping services using the label when the label is affixed or associated with a package. The provider may review past shipping data for the user and/or similar packages, and may determine whether the entered shipping data accurately estimates the user's shipping needs. If the past shipping data indicates that the user may require different shipping needs, such as additional value, the provider may adjust the value. Any over or under charge may then be refunded to the user on actual shipping of the package.