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be received by a recipient that is not S/MIME-compliant, rendering the original content unusable. To counter this problem, S/MIME uses an alternative structure, the multipart/signed MIME type. The body of the multipart/signed MIME type is made up of two parts. The first part, which can be of any MIME content type, is left in the clear and placed in the final message. The contents of the second part are a special case of signed data, known as a detached signature, which omits the copy of the plaintext that may be contained within the signed data. Figure 8-4 illustrates the S/MIME clear-signed data process.
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Figure 8-4 S/MIME clearsigned data process
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S/MIME also supports both encryption and signing. To provide this service, you can nest enveloped-only and signed-only data. In other words, you either sign a message first or envelope the message first. The decision of which process to perform first is up to the implementer and the user.
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The S/MIMEv3 specification (RFC2633) describes security risks involved with each technique (envelope first or signing first).
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In addition to security functions, S/MIME defines a format for conveying a request to have a public-key certificate issued. A MIME content type, application/x-pkcs10, is used to request a certificate from a certification authority.
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The specification does not mandate the use of any specific technique for requesting a certificate, whether it is through a certificate authority, a hardware token, or manual distribution. The specification does, however, mandate that every sending agent have a certificate.
Certificates-Only Messages
A certificates-only message is an application/pkcs7-mime and is prepared in much the same way as a signed-data message. This message, which is used to transport certificates to an S/MIME-compliant end entity, may be needed from time to time after a certification authority receives a certificate request. The certificates-only message can also be used for the transport of certificate revocation lists (CRLs).
Enhanced Security Services
Currently there are three optional enhanced security services that can be used to extend the current S/MIMEv3 security and certificate processing services.
Signed receipts A signed receipt is an optional service that allows for proof of message delivery. The receipt provides the originator a means of demonstrating to a third party that the recipient not only received but also verified the signature of the original message (hopefully, this means that the recipient also read the message). Ultimately, the recipient signs the entire message and its corresponding signature for proof of receipt. Note that this service is used only for signed data. Security labels Security labels can be used in a couple of ways. The first and probably most easily recognizable approach is to describe the sensitivity of data. A ranked list of labels is used (confidential, secret, restricted, and so on). Another technique is to use the labels to control authorization and access, describing which kind of recipient should have access to the data (such as a patient s doctor, medical billing agents, and so on). Secure mailing lists When S/MIME provides its services, sending agents must create recipient-specific data structures for each
Application-Layer Security Protocols
recipient. As the number of recipients grows for a given message, this processing can impair performance for messages sent out. Thus, mail list agents (MLAs) can take a single message and perform the recipient-specific encryption for every recipient.
Interoperability
Since the S/MIME standard first entered the public eye, a number of vendors have made efforts to incorporate it. However, a lack of interoperability is one pitfall that end users should take into account. For example, many vendors are still S/MIMEv2-compliant, whereas others have moved to S/MIMEv3 without supporting backward compatibility. Other problems include limits on the certificate processing available in various products. To help promote product interoperability, the RSA Interoperability Test Center was established. This S/MIME test center allows vendors to perform interoperability testing on their products and to have the results published. The following Web address provides interoperability information as well as products that have been found to be S/MIME-compliant: http://www.rsasecurity.com/standards/smime/interop_center.html.
Secure Electronic Transaction (SET)
The Internet has made it easier than ever for consumers to shop, money to be transferred, and bills to be paid over the Internet at the press of a button. The price we pay for this ease of use, however, is increased opportunity for fraud. For example, Figure 8-5 illustrates how easy it is for those with very little character to fraudulently generate credit cards used for online payment, known in the industry as payment cards. The Secure Electronic Transaction (SET) specification provides a framework for protecting payment cards used in Internet e-commerce transactions against fraud. SET protects payment cards by ensuring the confidentiality and integrity of the cardholder s data while at the same time providing a means of authentication of the card. The current version of the specification (SETv1) was initiated by MasterCard and Visa in February 1996 and was completed in May 1997. SET is defined in three books. The first book, Business Description, describes the specification in business terms (that is, goals, participants,
Figure 8-5
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