📄 rfc2311.txt
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messages SHOULD be used. - If the receiving agent has not yet created a list of capabilities for the sender's public key, then, after verifying the signature on the incoming message and checking the timestamp, the receiving agent SHOULD create a new list containing at least the signing time and the symmetric capabilities. - If such a list already exists, the receiving agent SHOULD verify that the signing time in the incoming message is greater than the signing time stored in the list and that the signature is valid. If so, the receiving agent SHOULD update both the signing time and capabilities in the list. Values of the signing time that lie far in the future (that is, a greater discrepancy than any reasonable clock skew), or a capabilitie lists in messages whose signature could not be verified, MUST NOT be accepted. The list of capabilities SHOULD be stored for future use in creating messages. Before sending a message, the sending agent MUST decide whether it is willing to use weak encryption for the particular data in theDusse, et. al. Informational [Page 7]RFC 2311 S/MIME Version 2 Message Specification March 1998 message. If the sending agent decides that weak encryption is unacceptable for this data, then the sending agent MUST NOT use a weak algorithm such as RC2/40. The decision to use or not use weak encryption overrides any other decision in this section about which encryption algorithm to use. Sections 2.6.2.1 through 2.6.2.4 describe the decisions a sending agent SHOULD use in deciding which type of encryption should be applied to a message. These rules are ordered, so the sending agent SHOULD make its decision in the order given.2.6.2.1 Rule 1: Known Capabilities If the sending agent has received a set of capabilities from the recipient for the message the agent is about to encrypt, then the sending agent SHOULD use that information by selecting the first capability in the list (that is, the capability most preferred by the intended recipient) for which the sending agent knows how to encrypt. The sending agent SHOULD use one of the capabilities in the list if the agent reasonably expects the recipient to be able to decrypt the message.2.6.2.2 Rule 2: Unknown Capabilities, Known Use of Encryption If: - the sending agent has no knowledge of the encryption capabilities of the recipient, - and the sending agent has received at least one message from the recipient, - and the last encrypted message received from the recipient had a trusted signature on it, then the outgoing message SHOULD use the same encryption algorithm as was used on the last signed and encrypted message received from the recipient.2.6.2.3 Rule 3: Unknown Capabilities, Risk of Failed Decryption If: - the sending agent has no knowledge of the encryption capabilities of the recipient, - and the sending agent is willing to risk that the recipient may not be able to decrypt the message, then the sending agent SHOULD use tripleDES.Dusse, et. al. Informational [Page 8]RFC 2311 S/MIME Version 2 Message Specification March 19982.6.2.4 Rule 4: Unknown Capabilities, No Risk of Failed Decryption If: - the sending agent has no knowledge of the encryption capabilities of the recipient, - and the sending agent is not willing to risk that the recipient may not be able to decrypt the message, then the sending agent MUST use RC2/40.2.6.3 Choosing Weak Encryption Like all algorithms that use 40 bit keys, RC2/40 is considered by many to be weak encryption. A sending agent that is controlled by a human SHOULD allow a human sender to determine the risks of sending data using RC2/40 or a similarly weak encryption algorithm before sending the data, and possibly allow the human to use a stronger encryption method such as tripleDES.2.6.4 Multiple Recipients If a sending agent is composing an encrypted message to a group of recipients where the encryption capabilities of some of the recipients do not overlap, the sending agent is forced to send more than one message. It should be noted that if the sending agent chooses to send a message encrypted with a strong algorithm, and then send the same message encrypted with a weak algorithm, someone watching the communications channel can decipher the contents of the strongly-encrypted message simply by decrypting the weakly-encrypted message.3. Creating S/MIME Messages This section describes the S/MIME message formats and how they are created. S/MIME messages are a combination of MIME bodies and PKCS objects. Several MIME types as well as several PKCS objects are used. The data to be secured is always a canonical MIME entity. The MIME entity and other data, such as certificates and algorithm identifiers, are given to PKCS processing facilities which produces a PKCS object. The PKCS object is then finally wrapped in MIME. S/MIME provides one format for enveloped-only data, several formats for signed-only data, and several formats for signed and enveloped data. Several formats are required to accommodate several environments, in particular for signed messages. The criteria for choosing among these formats are also described. The reader of this section is expected to understand MIME as described in [MIME-SPEC] and [MIME-SECURE].Dusse, et. al. Informational [Page 9]RFC 2311 S/MIME Version 2 Message Specification March 19983.1 Preparing the MIME Entity for Signing or Enveloping S/MIME is used to secure MIME entities. A MIME entity may be a sub- part, sub-parts of a message, or the whole message with all its sub- parts. A MIME entity that is the whole message includes only the MIME headers and MIME body, and does not include the RFC-822 headers. Note that S/MIME can also be used to secure MIME entities used in applications other than Internet mail. The MIME entity that is secured and described in this section can be thought of as the "inside" MIME entity. That is, it is the "innermost" object in what is possibly a larger MIME message. Processing "outside" MIME entities into PKCS #7 objects is described in Section 3.2, 3.4 and elsewhere. The procedure for preparing a MIME entity is given in [MIME-SPEC]. The same procedure is used here with some additional restrictions when signing. Description of the procedures from [MIME-SPEC] are repeated here, but the reader should refer to that document for the exact procedure. This section also describes additional requirements. A single procedure is used for creating MIME entities that are to be signed, enveloped, or both signed and enveloped. Some additional steps are recommended to defend against known corruptions that can occur during mail transport that are of particular importance for clear-signing using the multipart/signed format. It is recommended that these additional steps be performed on enveloped messages, or signed and enveloped messages in order that the message can be forwarded to any environment without modification. These steps are descriptive rather than prescriptive. The implementor is free to use any procedure as long as the result is the same. Step 1. The MIME entity is prepared according to the local conventions Step 2. The leaf parts of the MIME entity are converted to canonical form Step 3. Appropriate transfer encoding is applied to the leaves of the MIME entity When an S/MIME message is received, the security services on the message are removed, and the result is the MIME entity. That MIME entity is typically passed to a MIME-capable user agent where, it is further decoded and presented to the user or receiving application.Dusse, et. al. Informational [Page 10]RFC 2311 S/MIME Version 2 Message Specification March 19983.1.1 Canonicalization Each MIME entity MUST be converted to a canonical form that is uniquely and unambiguously representable in the environment where the signature is created and the environment where the signature will be verified. MIME entities MUST be canonicalized for enveloping as well as signing. The exact details of canonicalization depend on the actual MIME type and subtype of an entity, and are not described here. Instead, the standard for the particular MIME type should be consulted. For example, canonicalization of type text/plain is different from canonicalization of audio/basic. Other than text types, most types have only one representation regardless of computing platform or environment which can be considered their canonical representation. In general, canonicalization will be performed by the sending agent rather than the S/MIME implementation. The most common and important canonicalization is for text, which is often represented differently in different environments. MIME entities of major type "text" must have both their line endings and character set canonicalized. The line ending must be the pair of characters <CR><LF>, and the charset should be a registered charset [CHARSETS]. The details of the canonicalization are specified in [MIME-SPEC]. The chosen charset SHOULD be named in the charset parameter so that the receiving agent can unambiguously determine the charset used. Note that some charsets such as ISO-2022 have multiple representations for the same characters. When preparing such text for signing, the canonical representation specified for the charset MUST be used.3.1.2 Transfer Encoding When generating any of the secured MIME entities below, except the signing using the multipart/signed format, no transfer encoding at all is required. S/MIME implementations MUST be able to deal with binary MIME objects. If no Content-Transfer-Encoding header is present, the transfer encoding should be considered 7BIT. S/MIME implementations SHOULD however use transfer encoding described in section 3.1.3 for all MIME entities they secure. The reason for securing only 7-bit MIME entities, even for enveloped data that are not exposed to the transport, is that it allows the MIME entity to be handled in any environment without changing it. For example, a trusted gateway might remove the envelope, but not the signature, of a message, and then forward the signed message on to the endDusse, et. al. Informational [Page 11]RFC 2311 S/MIME Version 2 Message Specification March 1998 recipient so that they can verify the signatures directly. If the transport internal to the site is not 8-bit clean, such as on a wide-area network with a single mail gateway, verifying the signature will not be possible unless the original MIME entity was only 7-bit data.3.1.3 Transfer Encoding for Signing Using multipart/signed If a multipart/signed entity is EVER to be transmitted over the standard Internet SMTP infrastructure or other transport that is constrained to 7-bit text, it MUST have transfer encoding applied so that it is represented as 7-bit text. MIME entities that are 7-bit data already need no transfer encoding. Entities such as 8-bit text and binary data can be encoded with quoted-printable or base-64 transfer encoding. The primary reason for the 7-bit requirement is that the Internet mail transport infrastructure cannot guarantee transport of 8-bit or binary data. Even though many segments of the transport infrastructure now handle 8-bit and even binary data, it is sometimes not possible to know whether the transport path is 8-bit clear. If a mail message with 8-bit data were to encounter a message transfer agent that can not transmit 8-bit or binary data, the agent has three options, none of which are acceptable for a clear-signed message: - The agent could change the transfer encoding; this would invalidate the signature. - The agent could transmit the data anyway, which would most likely result in the 8th bit being corrupted; this too would invalidate the signature. - The agent could return the message to the sender. [MIME-SECURE] prohibits an agent from changing the transfer encoding of the first part of a multipart/signed message. If a compliant agent that can not transmit 8-bit or binary data encounters a multipart/signed message with 8-bit or binary data in the first part, it would have to return the message to the sender as undeliverable.3.1.4 Sample Canonical MIME Entity This example shows a multipart/mixed message with full transfer encoding. This message contains a text part and an attachment. The sample message text includes characters that are not US-ASCII and thus must be transfer encoded. Though not shown here, the end of each line is <CR><LF>. The line ending of the MIME headers, the text, and transfer encoded parts, all must be <CR><LF>. Note that this example is not of an S/MIME message.Dusse, et. al. Informational [Page 12]RFC 2311 S/MIME Version 2 Message Specification March 1998 Content-Type: multipart/mixed; boundary=bar --bar Content-Type: text/plain; charset=iso-8859-1 Content-Transfer-Encoding: quoted-printable =A1Hola Michael! How do you like the new S/MIME specification? I agree. It's generally a good idea to encode lines that begin with From=20because some mail transport agents will insert a greater- than (>) sign, thus invalidating the signature. Also, in some cases it might be desirable to encode any =20 trailing whitespace that occurs on lines in order to ensure =20 that the message signature is not invalidated when passing =20 a gateway that modifies such whitespace (like BITNET). =20 --bar Content-Type: image/jpeg Content-Transfer-Encoding: base64 iQCVAwUBMJrRF2N9oWBghPDJAQE9UQQAtl7LuRVndBjrk4EqYBIb3h5QXIX/LC// jJV5bNvkZIGPIcEmI5iFd9boEgvpirHtIREEqLQRkYNoBActFBZmh9GC3C041WGq uMbrbxc+nIs1TIKlA08rVi9ig/2Yh7LFrK5Ein57U/W72vgSxLhe/zhdfolT9Brn HOxEa44b+EI= --bar--3.2 The application/pkcs7-mime Type The application/pkcs7-mime type is used to carry PKCS #7 objects of several types including envelopedData and signedData. The details of constructing these entities is described in subsequent sections. This section describes the general characteristics of the application/pkcs7-mime type. This MIME type always carries a single PKCS #7 object. The PKCS #7 object must always be BER encoding of the ASN.1 syntax describing the object. The contentInfo field of the carried PKCS #7 object always contains a MIME entity that is prepared as described in section 3.1. The contentInfo field must never be empty. Since PKCS #7 objects are binary data, in most cases base-64 transfer encoding is appropriate, in particular when used with SMTP transport. The transfer encoding used depends on the transport through which the object is to be sent, and is not a characteristic of the MIME type.Dusse, et. al. Informational [Page 13]RFC 2311 S/MIME Version 2 Message Specification March 1998 Note that this discussion refers to the transfer encoding of the PKCS #7 object or "outside" MIME entity. It is completely distinct from,
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