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S/MIMEv3 implements support for several symmetric content-encryption algorithms. However, some S/MIME implementations still incorporate RC2 with a key size of 40 bits, and by today s standards, a 40-bit key is too weak. However, in most current S/MIMEv3 implementations, the user can choose from various content-encryption algorithms, such as DES, Triple DES, or RC2 with a key size greater than 40; see 2.
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The specification does, however, spell out all algorithms to be used for security services within S/MIMEv3. Some of them are optional, and others are required. They are as follows:
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Digest and hashing algorithms These must support MD5 and SHA-1; however, SHA-1 should be used. Digital signature algorithms Both sending and receiving agents must support DSA and should also support RSA. Key encryption algorithms Sending and receiving agents must support Diffie-Hellman and should also support RSA encryption. Data encryption (session key) algorithms Sending agents should support RC2/40-bit key, RC2/128-bit key, and Triple DES. Receiving agents should support RC2/128 and Triple DES but must support RC2/40.
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Which algorithm is best It s a simple matter of looking at key length; the bigger the key, the greater the security. However, sending and receiving agents are not always at the same level. For instance, the sending agent may be attempting to encrypt something with RC2/128 for added security; however, the receiving agent may only have the ability to decrypt messages with RC2/40. For this reason, the S/MIME specification defines a process for deciding which algorithm is best when you re sending S/MIME messages. The following are the specified rules that a sending agent should use in making its decision: 1. Known capabilities. If the sending agent has previously received a list of cryptographic capabilities of the recipient, the sender should choose the first (most preferred) capability listed to encrypt the outgoing message. 2. Unknown capabilities but known use of encryption. This rule applies when the sending agent has no idea of the encryption capabilities of the recipient but has received at least one previously encrypted message from that recipient. In this case, the sending agent should encrypt the outgoing message using that algorithm. 3. Unknown capabilities and unknown version of S/MIME. This rule applies when a sending agent has had no previous contact with the recipient and does not know its capabilities. The sending agent should use Triple DES because of its strength and because it is required by S/MIMEv3. However, if Triple DES is not used, the sending agent should use RC2/40.
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Application-Layer Security Protocols
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S/MIME messages are made up of the MIME bodies and CMS objects. The latter are derived from PKCS #7 data structures. Before any cryptographic processing takes place, a MIME entity must be prepared. A MIME entity may be a subpart of a message or the whole message, including all its subparts. The latter type of MIME entity is made up only of the MIME headers and MIME body and does not include the RFC822 headers (To:, From:, and so on). This MIME entity is then converted to canonical form, and the appropriate transfer encoding is applied (both processes are discussed in the following sections). After the MIME entity has been created and all proper encoding has taken place, the MIME entity is sent to security services, where the chosen security function is provided (enveloping, signing, or both). This process yields a CMS (or PKCS #7) object, which in turn is wrapped up in MIME and placed with the original message, according to the selected S/MIME content type.
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Canonicalization
As stated in the preceding section, each MIME entity must be converted to a canonical form. This conversion allows the MIME entity to be uniquely and unambiguously represented in the environments where the signature is created and where the signature will be verified. This same process is performed for MIME entities that will be digitally enveloped as well as signed. Canonicalization provides a standard means by which data from various platforms can be exchanged.
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