Provided are computer program product, system, and method for assessing a backup image comprising a backup of a source computer system to recover to a target computer system. A point-in-time backup image is selected from a plurality of backup images taken of an image on the source computer system, wherein the selected backup is to be applied to the target computer system. A determination is made from a plurality of retention policies applicable to files included in the source computer system a most restrictive retention policy. A determination is made as to whether the selected backup image satisfies the most restrictive retention policy. A retention status of the backup image is set based on whether the determined version of the selected backup satisfies the most restrictive retention policy. The retention status is presented for use in determining whether to use the selected backup image.