Systems and methods are described for better assessing risk associated with cashing second-party checks and other negotiable instruments. The systems and methods make use of information about authenticating marks, such as watermarks, bar codes, insignia, background patterns, and the like, from a check in order to better assess the legitimacy and cashability of the check. In various embodiments, information about an authenticating mark may be compared to stored information about an expected configuration for the authenticating mark. In various embodiments, a gradated risk score may be generated, based at least in part on the comparison. In various embodiments, the risk score may be combined with risk scores that are descriptive of other aspects of a check cashing transaction to calculate a risk score for the transaction as a whole. In some embodiments, the transaction risk score may be used to generate an accept/decline recommendation for the transaction.