A method includes obtaining information identifying a predicted trajectory of material-based measurements associated with a transfer of material. The method also includes obtaining actual material-based measurements during the transfer of the material and determining whether the actual material-based measurements fall outside of the predicted trajectory. The method further includes identifying a problem with the transfer of the material if at least one of the actual material-based measurements falls outside of the predicted trajectory. The method may also include generating the predicted trajectory of the material-based measurements using historical data associated with one or more prior transfers, such as historical data associated with at least one pump to be used during the transfer of the material. The actual material-based measurements could include measurements of a level and/or a volume of the material in a tank.