Packaging for retaining an article to be personalized in a predetermined position relative to the packaging may include a first container defining an interior cavity and an insert designed to retain the article in a predetermined position and orientation relative to the insert. The insert may be positioned within the interior cavity so that the article retained by the insert is within the interior cavity. At least one of the first container may define an opening designed to provide access to a personalization system for personalizing a predetermined surface of the article while the article is retained by the insert and the insert and article are positioned within the interior cavity so that the predetermined surface can be personalized based on the position of the first container relative to the personalization system.