A processing system is provided for regulatory or tax status certification of investors. Certificates are generated and synchronized with data. The certificates are indicative of entitlements to own or receive income on securities in accord with various governmental, tax or contractually determined constraints. Interest or dividend income can be paid to eligible investors free (or at reduced rates) of withholding tax once a valid certificate is obtained. Certificates can also be provided to permit a certified entity to purchase investments that are otherwise restricted from sale. Investors or investor banking representatives can introduce investor details into the system for use in generating certificates. Such certificates are sent out for execution (e.g., signature), and electronically transmitted back into the system. Tracking elements are provided to allow the certificates to be automatically matched to electronically stored investor data, thus forming the basis of an executed certification.