The present invention discloses a solution for providing item bagging advisements to individuals bagging purchased items during a check-out situation. The solution can include a self-checkout system and/or a human assisted checkout system capable of providing bagging assistance. A bagged item can be detected based on information such as weight, barcode data, and the like. Based on a set of rules for preferred item grouping, items can be determined to be appropriately bagged or to be in conflict with another item. Item bagging assistance can include, but is not limited to, item conflict warning, item compatibility confirmation, and assistance based on item categorization. Visual and aural confirmation and/or warning notifications can be presented to a user based on item compatibility or incompatibility.