A print driver's feature selection GUI can thus be utilized by a user to initiate a special, private print job when the user selects a feature, such as a picture Watermark, which is dependent on one or more files which are only present on the client (e.g., a client PC or other client computing device in a client-server printing environment). That private print job is used in a novel way as disclosed herein to “shuttle” the file to the print server. The print server interprets these private jobs in a special manner and caches the files contained within for use by subsequent normal print jobs. Unlike a normal print job, nothing will be sent to the printer in the case of these private print jobs.