A printing system includes one or more of information processing apparatuses, an image forming apparatus, a storage storing pieces of job information on print jobs, and circuitry. The circuitry is configured to execute: receiving the print target data from the information processing apparatus; receiving a history of pieces of job information corresponding to user identification information corresponding to the target data from the storage; estimating, based on the history, a type of a PDL to which the target data is converted; generating PDL data by converting the target data to the PDL of which the type is estimated; transmitting the PDL data to the image forming apparatus when the estimated PDL is available for the image forming apparatus; and selecting, when the estimated PDL is not available for the image forming apparatus, a PDL available for the image forming apparatus and re-converting the print target data to the selected PDL.