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Network Working Group                                B. Ramsdell, EditorRequest for Comments: 3851                                Sendmail, Inc.Obsoletes:2633                                                July 2004Category: Standards TrackSecure/Multipurpose Internet Mail Extensions (S/MIME) Version 3.1Message SpecificationStatus of this Memo   This document specifies an Internet standards track protocol for the   Internet community, and requests discussion and suggestions for   improvements.  Please refer to the current edition of the "Internet   Official Protocol Standards" (STD 1) for the standardization state   and status of this protocol.  Distribution of this memo is unlimited.Copyright Notice   Copyright (C) The Internet Society (2004).Abstract   This document defines Secure/Multipurpose Internet Mail Extensions   (S/MIME) version 3.1.  S/MIME provides a consistent way to send and   receive secure MIME data.  Digital signatures provide authentication,   message integrity, and non-repudiation with proof of origin.   Encryption provides data confidentiality.  Compression can be used to   reduce data size.  This document obsoletesRFC 2633.Table of Contents1.  Introduction . . . . . . . . . . . . . . . . . . . . . . . . .21.1.  Specification Overview . . . . . . . . . . . . . . . . .31.2.  Terminology. . . . . . . . . . . . . . . . . . . . . . .31.3.  Definitions. . . . . . . . . . . . . . . . . . . . . . .41.4.  Compatibility with Prior Practice of S/MIME. . . . . . .51.5.  Changes Since S/MIME v3. . . . . . . . . . . . . . . . .52.  CMS Options. . . . . . . . . . . . . . . . . . . . . . . . . .52.1.  DigestAlgorithmIdentifier. . . . . . . . . . . . . . . .52.2.  SignatureAlgorithmIdentifier . . . . . . . . . . . . . .62.3.  KeyEncryptionAlgorithmIdentifier . . . . . . . . . . . .62.4.  General Syntax . . . . . . . . . . . . . . . . . . . . .62.5.  Attributes and the SignerInfo Type . . . . . . . . . . .72.6.  SignerIdentifier SignerInfo Type . . . . . . . . . . . .112.7.  ContentEncryptionAlgorithmIdentifier . . . . . . . . . .123.  Creating S/MIME Messages . . . . . . . . . . . . . . . . . . .14Ramsdell                    Standards Track                     [Page 1]

RFC 3851            S/MIME 3.1 Message Specification           July 2004       3.1.  Preparing the MIME Entity for Signing, Enveloping             or Compressing . . . . . . . . . . . . . . . . . . . . .143.2.  The application/pkcs7-mime Type. . . . . . . . . . . . .193.3.  Creating an Enveloped-only Message . . . . . . . . . . .213.4.  Creating a Signed-only Message . . . . . . . . . . . . .223.5.  Creating an Compressed-only Message. . . . . . . . . . .263.6.  Multiple Operations. . . . . . . . . . . . . . . . . . .273.7.  Creating a Certificate Management Messagetoc . . . . . .273.8.  Registration Requests. . . . . . . . . . . . . . . . . .283.9.  Identifying an S/MIME Message. . . . . . . . . . . . . .284.  Certificate Processing . . . . . . . . . . . . . . . . . . . .294.1.  Key Pair Generation. . . . . . . . . . . . . . . . . . .295.  Security Considerations. . . . . . . . . . . . . . . . . . . .29A.  ASN.1 Module . . . . . . . . . . . . . . . . . . . . . . . . .31B.  References . . . . . . . . . . . . . . . . . . . . . . . . . .32B.1.  Normative References . . . . . . . . . . . . . . . . . .32B.2.  Informative References . . . . . . . . . . . . . . . . .34C.  Acknowledgements . . . . . . . . . . . . . . . . . . . . . . .35D.  Editor's Address . . . . . . . . . . . . . . . . . . . . . . .35       Full Copyright Statement . . . . . . . . . . . . . . . . . . .361.  Introduction   S/MIME (Secure/Multipurpose Internet Mail Extensions) provides a   consistent way to send and receive secure MIME data.  Based on the   popular Internet MIME standard, S/MIME provides the following   cryptographic security services for electronic messaging   applications:  authentication, message integrity and non-repudiation   of origin (using digital signatures), and data confidentiality (using   encryption).   S/MIME can be used by traditional mail user agents (MUAs) to add   cryptographic security services to mail that is sent, and to   interpret cryptographic security services in mail that is received.   However, S/MIME is not restricted to mail; it can be used with any   transport mechanism that transports MIME data, such as HTTP.  As   such, S/MIME takes advantage of the object-based features of MIME and   allows secure messages to be exchanged in mixed-transport systems.   Further, S/MIME can be used in automated message transfer agents that   use cryptographic security services that do not require any human   intervention, such as the signing of software-generated documents and   the encryption of FAX messages sent over the Internet.Ramsdell                    Standards Track                     [Page 2]

RFC 3851 S/MIME 3.1 Message Specification July 20041.1. Specification Overview This document describes a protocol for adding cryptographic signature and encryption services to MIME data. The MIME standard [MIME-SPEC] provides a general structure for the content type of Internet messages and allows extensions for new content type applications. This specification defines how to create a MIME body part that has been cryptographically enhanced according to CMS [CMS], which is derived from PKCS #7 [PKCS-7]. This specification also defines the application/pkcs7-mime MIME type that can be used to transport those body parts. This document also discusses how to use the multipart/signed MIME type defined in [MIME-SECURE] to transport S/MIME signed messages. multipart/signed is used in conjunction with the application/pkcs7- signature MIME type, which is used to transport a detached S/MIME signature. In order to create S/MIME messages, an S/MIME agent MUST follow the specifications in this document, as well as the specifications listed in the Cryptographic Message Syntax document [CMS] [CMSALG]. Throughout this specification, there are requirements and recommendations made for how receiving agents handle incoming messages. There are separate requirements and recommendations for how sending agents create outgoing messages. In general, the best strategy is to "be liberal in what you receive and conservative in what you send". Most of the requirements are placed on the handling of incoming messages while the recommendations are mostly on the creation of outgoing messages. The separation for requirements on receiving agents and sending agents also derives from the likelihood that there will be S/MIME systems that involve software other than traditional Internet mail clients. S/MIME can be used with any system that transports MIME data. An automated process that sends an encrypted message might not be able to receive an encrypted message at all, for example. Thus, the requirements and recommendations for the two types of agents are listed separately when appropriate.1.2. Terminology The key words "MUST", "MUST NOT", "REQUIRED", "SHALL", "SHALL NOT", "SHOULD", "SHOULD NOT", "RECOMMENDED", "MAY", and "OPTIONAL" in this document are to be interpreted as described in [MUSTSHOULD].Ramsdell Standards Track [Page 3]

RFC 3851            S/MIME 3.1 Message Specification           July 20041.3.  Definitions   For the purposes of this specification, the following definitions   apply.   ASN.1: Abstract Syntax Notation One, as defined in CCITT X.208   [X.208-88].   BER: Basic Encoding Rules for ASN.1, as defined in CCITT X.209   [X.209-88].   Certificate: A type that binds an entity's name to a public key with   a digital signature.   DER: Distinguished Encoding Rules for ASN.1, as defined in CCITT   X.509 [X.509-88].   7-bit data: Text data with lines less than 998 characters long, where   none of the characters have the 8th bit set, and there are no NULL   characters.  <CR> and <LF> occur only as part of a <CR><LF> end of   line delimiter.   8-bit data: Text data with lines less than 998 characters, and where   none of the characters are NULL characters. <CR> and <LF> occur only   as part of a <CR><LF> end of line delimiter.   Binary data: Arbitrary data.   Transfer Encoding: A reversible transformation made on data so 8-bit   or binary data can be sent via a channel that only transmits 7-bit   data.   Receiving agent: Software that interprets and processes S/MIME CMS   objects, MIME body parts that contain CMS content types, or both.   Sending agent: Software that creates S/MIME CMS content types, MIME   body parts that contain CMS content types, or both.   S/MIME agent: User software that is a receiving agent, a sending   agent, or both.Ramsdell                    Standards Track                     [Page 4]

RFC 3851            S/MIME 3.1 Message Specification           July 20041.4.  Compatibility with Prior Practice of S/MIME   S/MIME version 3.1 agents SHOULD attempt to have the greatest   interoperability possible with agents for prior versions of S/MIME.   S/MIME version 2 is described inRFC 2311 throughRFC 2315, inclusive   and S/MIME version 3 is described inRFC 2630 throughRFC 2634   inclusive.RFC 2311 also has historical information about the   development of S/MIME.1.5.  Changes Since S/MIME v3   The RSA public key algorithm was changed to a MUST implement key   wrapping algorithm, and the Diffie-Hellman algorithm changed to a   SHOULD implement.   The AES symmetric encryption algorithm has been included as a SHOULD   implement.   The RSA public key algorithm was changed to a MUST implement   signature algorithm.   Ambiguous language about the use of "empty" SignedData messages to   transmit certificates was clarified to reflect that transmission of   certificate revocation lists is also allowed.   The use of binary encoding for some MIME entities is now explicitly   discussed.   Header protection through the use of the message/rfc822 MIME type has   been added.   Use of the CompressedData CMS type is allowed, along with required   MIME type and file extension additions.2.  CMS Options   CMS allows for a wide variety of options in content and algorithm   support.  This section puts forth a number of support requirements   and recommendations in order to achieve a base level of   interoperability among all S/MIME implementations. [CMSALG] provides   additional details regarding the use of the cryptographic algorithms.2.1.  DigestAlgorithmIdentifier   Sending and receiving agents MUST support SHA-1 [CMSALG].  Receiving   agents SHOULD support MD5 [CMSALG] for the purpose of providing   backward compatibility with MD5-digested S/MIME v2 SignedData   objects.Ramsdell                    Standards Track                     [Page 5]

RFC 3851 S/MIME 3.1 Message Specification July 20042.2. SignatureAlgorithmIdentifier Receiving agents MUST support id-dsa-with-sha1 defined in [CMSALG]. The algorithm parameters MUST be absent (not encoded as NULL). Receiving agents MUST support rsaEncryption, defined in [CMSALG]. Sending agents MUST support either id-dsa-with-sha1 or rsaEncryption. If using rsaEncryption, sending and receiving agents MUST support the digest algorithms insection 2.1 as specified. Note that S/MIME v3 clients might only implement signing or signature verification using id-dsa-with-sha1, and might also use id-dsa as an AlgorithmIdentifier in this field. Receiving clients SHOULD recognize id-dsa as equivalent to id-dsa-with-sha1, and sending clients MUST use id-dsa-with-sha1 if using that algorithm. Also note that S/MIME v2 clients are only required to verify digital signatures using the rsaEncryption algorithm with SHA-1 or MD5, and might not implement id-dsa-with-sha1 or id-dsa at all.2.3. KeyEncryptionAlgorithmIdentifier Sending and receiving agents MUST support rsaEncryption, defined in [CMSALG]. Sending and receiving agents SHOULD support Diffie-Hellman defined in [CMSALG], using the ephemeral-static mode. Note that S/MIME v3 clients might only implement key encryption and decryption using the Diffie-Hellman algorithm. Also note that S/MIME v2 clients are only capable of decrypting content-encryption keys using the rsaEncryption algorithm.2.4. General Syntax There are several CMS content types. Of these, only the Data, SignedData, EnvelopedData, and CompressedData content types are currently used for S/MIME.2.4.1. Data Content Type Sending agents MUST use the id-data content type identifier to identify the "inner" MIME message content. For example, when applying a digital signature to MIME data, the CMS SignedData encapContentInfo eContentType MUST include the id-data object identifier and the MIME content MUST be stored in the SignedData encapContentInfo eContent OCTET STRING (unless the sending agent is using multipart/signed, in which case the eContent is absent, perRamsdell Standards Track [Page 6]

RFC 3851 S/MIME 3.1 Message Specification July 2004section 3.4.3 of this document). As another example, when applying encryption to MIME data, the CMS EnvelopedData encryptedContentInfo contentType MUST include the id-data object identifier and the encrypted MIME content MUST be stored in the EnvelopedData encryptedContentInfo encryptedContent OCTET STRING.2.4.2. SignedData Content Type Sending agents MUST use the SignedData content type to apply a digital signature to a message or, in a degenerate case where there is no signature information, to convey certificates. Applying a signature to a message provides authentication, message integrity, and non-repudiation of origin.2.4.3. EnvelopedData Content Type This content type is used to apply data confidentiality to a message. A sender needs to have access to a public key for each intended message recipient to use this service.2.4.4. CompressedData Content Type This content type is used to apply data compression to a message. This content type does not provide authentication, message integrity, non-repudiation, or data confidentiality, and is only used to reduce message size. Seesection 3.6 for further guidance on the use of this type in conjunction with other CMS types.2.5. Attributes and the SignerInfo Type The SignerInfo type allows the inclusion of unsigned and signed attributes to be included along with a signature. Receiving agents MUST be able to handle zero or one instance of each of the signed attributes listed here. Sending agents SHOULD generate one instance of each of the following signed attributes in each S/MIME message: - signingTime (section 2.5.1 in this document) - sMIMECapabilities (section 2.5.2 in this document) - sMIMEEncryptionKeyPreference (section 2.5.3 in this document) - id-messageDigest (section 11.2 in [CMS]) - id-contentType (section 11.1 in [CMS])Ramsdell Standards Track [Page 7]

RFC 3851 S/MIME 3.1 Message Specification July 2004 Further, receiving agents SHOULD be able to handle zero or one instance in the signingCertificate signed attribute, as defined in section 5 of [ESS]. Sending agents SHOULD generate one instance of the signingCertificate signed attribute in each SignerInfo structure. Additional attributes and values for these attributes might be defined in the future. Receiving agents SHOULD handle attributes or values that it does not recognize in a graceful manner. Interactive sending agents that include signed attributes that are not listed here SHOULD display those attributes to the user, so that the user is aware of all of the data being signed.2.5.1. Signing-Time Attribute The signing-time attribute is used to convey the time that a message was signed. The time of signing will most likely be created by a message originator and therefore is only as trustworthy as the originator. Sending agents MUST encode signing time through the year 2049 as UTCTime; signing times in 2050 or later MUST be encoded as GeneralizedTime. When the UTCTime CHOICE is used, S/MIME agents MUST interpret the year field (YY) as follows: if YY is greater than or equal to 50, the year is interpreted as 19YY; if YY is less than 50, the year is interpreted as 20YY.2.5.2. SMIMECapabilities Attribute The SMIMECapabilities attribute includes signature algorithms (such as "sha1WithRSAEncryption"), symmetric algorithms (such as "DES- EDE3-CBC"), and key encipherment algorithms (such as "rsaEncryption"). There are also several identifiers which indicate support for other optional features such as binary encoding and compression. The SMIMECapabilities were designed to be flexible and extensible so that, in the future, a means of identifying other capabilities and preferences such as certificates can be added in a way that will not cause current clients to break. If present, the SMIMECapabilities attribute MUST be a SignedAttribute; it MUST NOT be an UnsignedAttribute. CMS defines SignedAttributes as a SET OF Attribute. The SignedAttributes in a signerInfo MUST NOT include multiple instances of the SMIMECapabilities attribute. CMS defines the ASN.1 syntax for Attribute to include attrValues SET OF AttributeValue. ARamsdell Standards Track [Page 8]

RFC 3851            S/MIME 3.1 Message Specification           July 2004   SMIMECapabilities attribute MUST only include a single instance of   AttributeValue.  There MUST NOT be zero or multiple instances of   AttributeValue present in the attrValues SET OF AttributeValue.   The semantics of the SMIMECapabilities attribute specify a partial   list as to what the client announcing the SMIMECapabilities can   support.  A client does not have to list every capability it   supports, and need not list all its capabilities so that the   capabilities list doesn't get too long.  In an SMIMECapabilities   attribute, the object identifiers (OIDs) are listed in order of their   preference, but SHOULD be separated logically along the lines of   their categories (signature algorithms, symmetric algorithms, key   encipherment algorithms, etc.)   The structure of the SMIMECapabilities attribute is to facilitate   simple table lookups and binary comparisons in order to determine   matches.  For instance, the DER-encoding for the SMIMECapability for   DES EDE3 CBC MUST be identically encoded regardless of the   implementation.  Because of the requirement for identical encoding,   individuals documenting algorithms to be used in the   SMIMECapabilities attribute SHOULD explicitly document the correct   byte sequence for the common cases.   For any capability, the associated parameters for the OID MUST   specify all of the parameters necessary to differentiate between two   instances of the same algorithm.  For instance, the number of rounds   and the block size for RC5 needs to be specified in addition to the   key length.   The OIDs that correspond to algorithms SHOULD use the same OID as the   actual algorithm, except in the case where the algorithm usage is   ambiguous from the OID.  For instance, in an earlier specification,   rsaEncryption was ambiguous because it could refer to either a   signature algorithm or a key encipherment algorithm.  In the event   that an OID is ambiguous, it needs to be arbitrated by the maintainer   of the registered SMIMECapabilities list as to which type of   algorithm will use the OID, and a new OID MUST be allocated under the   smimeCapabilities OID to satisfy the other use of the OID.   The registered SMIMECapabilities list specifies the parameters for   OIDs that need them, most notably key lengths in the case of   variable-length symmetric ciphers.  In the event that there are no   differentiating parameters for a particular OID, the parameters MUST   be omitted, and MUST NOT be encoded as NULL.Ramsdell                    Standards Track                     [Page 9]

RFC 3851 S/MIME 3.1 Message Specification July 2004 Additional values for the SMIMECapabilities attribute might be defined in the future. Receiving agents MUST handle a SMIMECapabilities object that has values that it does not recognize in a graceful manner.Section 2.7.1 explains a strategy for caching capabilities.2.5.2.1. SMIMECapability For the RC2 Algorithm For the RC2 algorithm preference SMIMECapability, the capabilityID MUST be set to the value rc2-cbc as defined in [CMSALG]. The parameters field MUST contain SMIMECapabilitiesParametersForRC2CBC (seeappendix A). Please note that the SMIMECapabilitiesParametersForRC2CBC is a single INTEGER which contains the effective key length (NOT the corresponding RC2 parameter version value). So, for example, for RC2 with a 128-bit effective key length, the parameter would be encoded as the INTEGER value 128, NOT the corresponding parameter version of 58.2.5.3. Encryption Key Preference Attribute The encryption key preference attribute allows the signer to unambiguously describe which of the signer's certificates has the signer's preferred encryption key. This attribute is designed to enhance behavior for interoperating with those clients that use separate keys for encryption and signing. This attribute is used to convey to anyone viewing the attribute which of the listed certificates is appropriate for encrypting a session key for future encrypted messages. If present, the SMIMEEncryptionKeyPreference attribute MUST be a SignedAttribute; it MUST NOT be an UnsignedAttribute. CMS defines SignedAttributes as a SET OF Attribute. The SignedAttributes in a signerInfo MUST NOT include multiple instances of the SMIMEEncryptionKeyPreference attribute. CMS defines the ASN.1 syntax for Attribute to include attrValues SET OF AttributeValue. A SMIMEEncryptionKeyPreference attribute MUST only include a single instance of AttributeValue. There MUST NOT be zero or multiple instances of AttributeValue present in the attrValues SET OF AttributeValue. The sending agent SHOULD include the referenced certificate in the set of certificates included in the signed message if this attribute is used. The certificate MAY be omitted if it has been previously made available to the receiving agent. Sending agents SHOULD use this attribute if the commonly used or preferred encryptionRamsdell Standards Track [Page 10]

RFC 3851            S/MIME 3.1 Message Specification           July 2004   certificate is not the same as the certificate used to sign the   message.   Receiving agents SHOULD store the preference data if the signature on   the message is valid and the signing time is greater than the   currently stored value. (As with the SMIMECapabilities, the clock   skew SHOULD be checked and the data not used if the skew is too   great.)  Receiving agents SHOULD respect the sender's encryption key   preference attribute if possible.  This, however, represents only a   preference and the receiving agent can use any certificate in   replying to the sender that is valid.Section 2.7.1 explains a strategy for caching preference data.2.5.3.1.  Selection of Recipient Key Management Certificate   In order to determine the key management certificate to be used when   sending a future CMS EnvelopedData message for a particular   recipient, the following steps SHOULD be followed:   -  If an SMIMEEncryptionKeyPreference attribute is found in a      SignedData object received from the desired recipient, this      identifies the X.509 certificate that SHOULD be used as the X.509      key management certificate for the recipient.   -  If an SMIMEEncryptionKeyPreference attribute is not found in a      SignedData object received from the desired recipient, the set of      X.509 certificates SHOULD be searched for a X.509 certificate with      the same subject name as the signing of a X.509 certificate which      can be used for key management.   -  Or use some other method of determining the user's key management      key.  If a X.509 key management certificate is not found, then      encryption cannot be done with the signer of the message.  If      multiple X.509 key management certificates are found, the S/MIME      agent can make an arbitrary choice between them.2.6.  SignerIdentifier SignerInfo Type   S/MIME v3.1 implementations MUST support both issuerAndSerialNumber   as well as subjectKeyIdentifier.  Messages that use the   subjectKeyIdentifier choice cannot be read by S/MIME v2 clients.   It is important to understand that some certificates use a value for   subjectKeyIdentifier that is not suitable for uniquely identifying a   certificate.  Implementations MUST be prepared for multiple   certificates for potentially different entities to have the same   value for subjectKeyIdentifier, and MUST be prepared to try eachRamsdell                    Standards Track                    [Page 11]

RFC 3851            S/MIME 3.1 Message Specification           July 2004   matching certificate during signature verification before indicating   an error condition.2.7.  ContentEncryptionAlgorithmIdentifier   Sending and receiving agents MUST support encryption and decryption   with DES EDE3 CBC, hereinafter called "tripleDES" [CMSALG].   Receiving agents SHOULD support encryption and decryption using the   RC2 [CMSALG] or a compatible algorithm at a key size of 40 bits,   hereinafter called "RC2/40".  Sending and receiving agents SHOULD   support encryption and decryption with AES [CMSAES] at a key size of   128, 192, and 256 bits.2.7.1.  Deciding Which Encryption Method To Use   When a sending agent creates an encrypted message, it has to decide   which type of encryption to use.  The decision process involves using   information garnered from the capabilities lists included in messages   received from the recipient, as well as out-of-band information such   as private agreements, user preferences, legal restrictions, and so   on.Section 2.5.2 defines a method by which a sending agent can   optionally announce, among other things, its decrypting capabilities   in its order of preference.  The following method for processing and   remembering the encryption capabilities attribute in incoming signed   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 capabilities list 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 theRamsdell                    Standards Track                    [Page 12]

RFC 3851            S/MIME 3.1 Message Specification           July 2004   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.   Sections2.7.2.1 through2.7.2.4 describe the decisions a sending   agent SHOULD use in deciding which type of encryption will be applied   to a message.  These rules are ordered, so the sending agent SHOULD   make its decision in the order given.2.7.1.1.  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) that 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.2.7.1.2.  Rule 2: Unknown Capabilities, Unknown Version of S/MIME   If the following two conditions are met:   -  the sending agent has no knowledge of the encryption capabilities      of the recipient,   -  and the sending agent has no knowledge of the version of S/MIME of      the recipient,   then the sending agent SHOULD use tripleDES because it is a stronger   algorithm and is required by S/MIME v3.  If the sending agent chooses   not to use tripleDES in this step, it SHOULD use RC2/40.2.7.2.  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.2.7.3.  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.  Please note that if the sending agent chooses toRamsdell                    Standards Track                    [Page 13]

RFC 3851 S/MIME 3.1 Message Specification July 2004 send a message encrypted with a strong algorithm, and then send the same message encrypted with a weak algorithm, someone watching the communications channel could learn 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 CMS content types. Several MIME types as well as several CMS content types 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 CMS processing facilities which produce a CMS object. Finally, the CMS object is wrapped in MIME. The Enhanced Security Services for S/MIME [ESS] document provides descriptions of how nested, secured S/MIME messages are formatted. ESS provides a description of how a triple-wrapped S/MIME message is formatted using multipart/signed and application/pkcs7-mime for the signatures. 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].3.1. Preparing the MIME Entity for Signing, Enveloping or Compressing S/MIME is used to secure MIME entities. A MIME entity can 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 theRFC-822 headers. Note that S/MIME can also be used to secure MIME entities used in applications other than Internet mail. If protection of theRFC-822 headers is required, the use of the message/rfc822 MIME type is explained later in this section. 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 CMS content types is described inSection 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 restrictionsRamsdell Standards Track [Page 14]

RFC 3851 S/MIME 3.1 Message Specification July 2004 when signing. Description of the procedures from [MIME-SPEC] are repeated here, but it is suggested that the reader 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 have any combination of signing, enveloping, and compressing applied. 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, so that the message can be forwarded to any environment without modification. These steps are descriptive rather than prescriptive. The implementer 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 processed, 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. In order to protect outer, non-content related message headers (for instance, the "Subject", "To", "From" and "CC" fields), the sending client MAY wrap a full MIME message in a message/rfc822 wrapper in order to apply S/MIME security services to these headers. It is up to the receiving client to decide how to present these "inner" headers along with the unprotected "outer" headers. When an S/MIME message is received, if the top-level protected MIME entity has a Content-Type of message/rfc822, it can be assumed that the intent was to provide header protection. This entity SHOULD be presented as the top-level message, taking into account header merging issues as previously discussed.Ramsdell Standards Track [Page 15]

RFC 3851 S/MIME 3.1 Message Specification July 20043.1.1. 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 and compressing 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 non-security part of 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 is required at all. S/MIME implementations MUST be able to deal with binary MIME objects. If no Content-Transfer-Encoding header is present, the transfer encoding is presumed to be 7BIT. S/MIME implementations SHOULD however use transfer encoding described insection 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 endRamsdell Standards Track [Page 16]

RFC 3851            S/MIME 3.1 Message Specification           July 2004   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.   S/MIME implementations which "know" that all intended recipient(s)   are capable of handling inner (all but the outermost) binary MIME   objects SHOULD use binary encoding as opposed to a 7-bit-safe   transfer encoding for the inner entities.  The use of a 7-bit-safe   encoding (such as base64) would unnecessarily expand the message   size.  Implementations MAY "know" that recipient implementations are   capable of handling inner binary MIME entities either by interpreting   the id-cap-preferBinaryInside sMIMECapabilities attribute, by prior   agreement, or by other means.   If one or more intended recipients are unable to handle inner binary   MIME objects, or if this capability is unknown for any of the   intended recipients, S/MIME implementations SHOULD use transfer   encoding described insection 3.1.3 for all MIME entities they   secure.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 clean.  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.Ramsdell                    Standards Track                    [Page 17]

RFC 3851 S/MIME 3.1 Message Specification July 2004 [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 need to 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. 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? 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--Ramsdell Standards Track [Page 18]

RFC 3851 S/MIME 3.1 Message Specification July 20043.2. The application/pkcs7-mime Type The application/pkcs7-mime type is used to carry CMS content types including EnvelopedData, SignedData, and CompressedData. The details of constructing these entities is described in subsequent sections. This section describes the general characteristics of the application/pkcs7-mime type. The carried CMS object always contains a MIME entity that is prepared as described insection 3.1 if the eContentType is id-data. Other contents MAY be carried when the eContentType contains different values. See [ESS] for an example of this with signed receipts. Since CMS content types 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. Note that this discussion refers to the transfer encoding of the CMS object or "outside" MIME entity. It is completely distinct from, and unrelated to, the transfer encoding of the MIME entity secured by the CMS object, the "inside" object, which is described insection 3.1. Because there are several types of application/pkcs7-mime objects, a sending agent SHOULD do as much as possible to help a receiving agent know about the contents of the object without forcing the receiving agent to decode the ASN.1 for the object. The MIME headers of all application/pkcs7-mime objects SHOULD include the optional "smime- type" parameter, as described in the following sections.3.2.1. The name and filename Parameters For the application/pkcs7-mime, sending agents SHOULD emit the optional "name" parameter to the Content-Type field for compatibility with older systems. Sending agents SHOULD also emit the optional Content-Disposition field [CONTDISP] with the "filename" parameter. If a sending agent emits the above parameters, the value of the parameters SHOULD be a file name with the appropriate extension:Ramsdell Standards Track [Page 19]

RFC 3851 S/MIME 3.1 Message Specification July 2004 MIME Type File Extension application/pkcs7-mime (SignedData, EnvelopedData) .p7m application/pkcs7-mime (degenerate SignedData .p7c certificate management message) application/pkcs7-mime (CompressedData) .p7z application/pkcs7-signature (SignedData) .p7s In addition, the file name SHOULD be limited to eight characters followed by a three letter extension. The eight character filename base can be any distinct name; the use of the filename base "smime" SHOULD be used to indicate that the MIME entity is associated with S/MIME. Including a file name serves two purposes. It facilitates easier use of S/MIME objects as files on disk. It also can convey type information across gateways. When a MIME entity of type application/pkcs7-mime (for example) arrives at a gateway that has no special knowledge of S/MIME, it will default the entity's MIME type to application/octet-stream and treat it as a generic attachment, thus losing the type information. However, the suggested filename for an attachment is often carried across a gateway. This often allows the receiving systems to determine the appropriate application to hand the attachment off to, in this case, a stand-alone S/MIME processing application. Note that this mechanism is provided as a convenience for implementations in certain environments. A proper S/MIME implementation MUST use the MIME types and MUST NOT rely on the file extensions.3.2.2. The smime-type parameter The application/pkcs7-mime content type defines the optional "smime- type" parameter. The intent of this parameter is to convey details about the security applied (signed or enveloped) along with information about the contained content. This specification defines the following smime-types.Ramsdell Standards Track [Page 20]

RFC 3851 S/MIME 3.1 Message Specification July 2004 Name CMS type Inner Content enveloped-data EnvelopedData id-data signed-data SignedData id-data certs-only SignedData none compressed-data CompressedData id-data In order for consistency to be obtained with future specifications, the following guidelines SHOULD be followed when assigning a new smime-type parameter. 1. If both signing and encryption can be applied to the content, then two values for smime-type SHOULD be assigned "signed-*" and "encrypted-*". If one operation can be assigned then this can be omitted. Thus since "certs-only" can only be signed, "signed-" is omitted. 2. A common string for a content OID SHOULD be assigned. We use "data" for the id-data content OID when MIME is the inner content. 3. If no common string is assigned. Then the common string of "OID.<oid>" is recommended (for example, "OID.1.3.6.1.5.5.7.6.1" would be DES40). It is explicitly intended that this field be a suitable hint for mail client applications to indicate whether a message is "signed" or "encrypted" without having to tunnel into the CMS payload.3.3. Creating an Enveloped-only Message This section describes the format for enveloping a MIME entity without signing it. It is important to note that sending enveloped but not signed messages does not provide for data integrity. It is possible to replace ciphertext in such a way that the processed message will still be valid, but the meaning can be altered. Step 1. The MIME entity to be enveloped is prepared according tosection 3.1. Step 2. The MIME entity and other required data is processed into a CMS object of type EnvelopedData. In addition to encrypting a copy of the content-encryption key for each recipient, a copy of the content-encryption key SHOULD be encrypted for the originator and included in the EnvelopedData (see [CMS]Section 6).Ramsdell Standards Track [Page 21]

RFC 3851 S/MIME 3.1 Message Specification July 2004 Step 3. The EnvelopedData object is wrapped in a CMS ContentInfo object. Step 4. The ContentInfo object is inserted into an application/pkcs7-mime MIME entity. The smime-type parameter for enveloped-only messages is "enveloped- data". The file extension for this type of message is ".p7m". A sample message would be: Content-Type: application/pkcs7-mime; smime-type=enveloped-data; name=smime.p7m Content-Transfer-Encoding: base64 Content-Disposition: attachment; filename=smime.p7m rfvbnj756tbBghyHhHUujhJhjH77n8HHGT9HG4VQpfyF467GhIGfHfYT6 7n8HHGghyHhHUujhJh4VQpfyF467GhIGfHfYGTrfvbnjT6jH7756tbB9H f8HHGTrfvhJhjH776tbB9HG4VQbnj7567GhIGfHfYT6ghyHhHUujpfyF4 0GhIGfHfQbnj756YT64V3.4. Creating a Signed-only Message There are two formats for signed messages defined for S/MIME: application/pkcs7-mime with SignedData, and multipart/signed. In general, the multipart/signed form is preferred for sending, and receiving agents MUST be able to handle both.3.4.1. Choosing a Format for Signed-only Messages There are no hard-and-fast rules when a particular signed-only format is chosen because it depends on the capabilities of all the receivers and the relative importance of receivers with S/MIME facilities being able to verify the signature versus the importance of receivers without S/MIME software being able to view the message. Messages signed using the multipart/signed format can always be viewed by the receiver whether they have S/MIME software or not. They can also be viewed whether they are using a MIME-native user agent or they have messages translated by a gateway. In this context, "be viewed" means the ability to process the message essentially as if it were not a signed message, including any other MIME structure the message might have.Ramsdell Standards Track [Page 22]

RFC 3851 S/MIME 3.1 Message Specification July 2004 Messages signed using the SignedData format cannot be viewed by a recipient unless they have S/MIME facilities. However, the SignedData format protects the message content from being changed by benign intermediate agents. Such agents might do line wrapping or content-transfer encoding changes which would break the signature.3.4.2. Signing Using application/pkcs7-mime with SignedData This signing format uses the application/pkcs7-mime MIME type. The steps to create this format are: Step 1. The MIME entity is prepared according tosection 3.1. Step 2. The MIME entity and other required data is processed into a CMS object of type SignedData. Step 3. The SignedData object is wrapped in a CMS ContentInfo object. Step 4. The ContentInfo object is inserted into an application/pkcs7-mime MIME entity. The smime-type parameter for messages using application/pkcs7-mime with SignedData is "signed-data". The file extension for this type of message is ".p7m". A sample message would be: Content-Type: application/pkcs7-mime; smime-type=signed-data; name=smime.p7m Content-Transfer-Encoding: base64 Content-Disposition: attachment; filename=smime.p7m 567GhIGfHfYT6ghyHhHUujpfyF4f8HHGTrfvhJhjH776tbB9HG4VQbnj7 77n8HHGT9HG4VQpfyF467GhIGfHfYT6rfvbnj756tbBghyHhHUujhJhjH HUujhJh4VQpfyF467GhIGfHfYGTrfvbnjT6jH7756tbB9H7n8HHGghyHh 6YT64V0GhIGfHfQbnj753.4.3. Signing Using the multipart/signed Format This format is a clear-signing format. Recipients without any S/MIME or CMS processing facilities are able to view the message. It makes use of the multipart/signed MIME type described in [MIME-SECURE]. The multipart/signed MIME type has two parts. The first part contains the MIME entity that is signed; the second part contains the "detached signature" CMS SignedData object in which the encapContentInfo eContent field is absent.Ramsdell Standards Track [Page 23]

RFC 3851 S/MIME 3.1 Message Specification July 20043.4.3.1. The application/pkcs7-signature MIME Type This MIME type always contains a CMS ContentInfo containing a single CMS object of type SignedData. The SignedData encapContentInfo eContent field MUST be absent. The signerInfos field contains the signatures for the MIME entity. The file extension for signed-only messages using application/pkcs7- signature is ".p7s".3.4.3.2. Creating a multipart/signed Message Step 1. The MIME entity to be signed is prepared according tosection 3.1, taking special care for clear-signing. Step 2. The MIME entity is presented to CMS processing in order to obtain an object of type SignedData in which the encapContentInfo eContent field is absent. Step 3. The MIME entity is inserted into the first part of a multipart/signed message with no processing other than that described insection 3.1. Step 4. Transfer encoding is applied to the "detached signature" CMS SignedData object and it is inserted into a MIME entity of type application/pkcs7-signature. Step 5. The MIME entity of the application/pkcs7-signature is inserted into the second part of the multipart/signed entity. The multipart/signed Content type has two required parameters: the protocol parameter and the micalg parameter. The protocol parameter MUST be "application/pkcs7-signature". Note that quotation marks are required around the protocol parameter because MIME requires that the "/" character in the parameter value MUST be quoted. The micalg parameter allows for one-pass processing when the signature is being verified. The value of the micalg parameter is dependent on the message digest algorithm(s) used in the calculation of the Message Integrity Check. If multiple message digest algorithms are used they MUST be separated by commas per [MIME- SECURE]. The values to be placed in the micalg parameter SHOULD be from the following:Ramsdell Standards Track [Page 24]

RFC 3851            S/MIME 3.1 Message Specification           July 2004   Algorithm   Value   used   MD5         md5   SHA-1       sha1   SHA-256     sha256   SHA-384     sha384   SHA-512     sha512   Any other   (defined separately in algorithm profile or "unknown"                if not defined)   (Historical note: some early implementations of S/MIME emitted and   expected "rsa-md5" and "rsa-sha1" for the micalg parameter.)   Receiving agents SHOULD be able to recover gracefully from a micalg   parameter value that they do not recognize.   The SHA-256, SHA-384, and SHA-512 algorithms [FIPS180-2] are not   currently recommended in S/MIME, and are included here for   completeness.3.4.3.3.  Sample multipart/signed Message       Content-Type: multipart/signed;          protocol="application/pkcs7-signature";          micalg=sha1; boundary=boundary42       --boundary42       Content-Type: text/plain       This is a clear-signed message.       --boundary42       Content-Type: application/pkcs7-signature; name=smime.p7s       Content-Transfer-Encoding: base64       Content-Disposition: attachment; filename=smime.p7s       ghyHhHUujhJhjH77n8HHGTrfvbnj756tbB9HG4VQpfyF467GhIGfHfYT6       4VQpfyF467GhIGfHfYT6jH77n8HHGghyHhHUujhJh756tbB9HGTrfvbnj       n8HHGTrfvhJhjH776tbB9HG4VQbnj7567GhIGfHfYT6ghyHhHUujpfyF4       7GhIGfHfYT64VQbnj756       --boundary42--Ramsdell                    Standards Track                    [Page 25]

RFC 3851            S/MIME 3.1 Message Specification           July 2004   The content that is digested (the first part of the multipart/signed)   are the bytes:   43 6f 6e 74 65 6e 74 2d 54 79 70 65 3a 20 74 65 78 74 2f 70 6c 61 69   6e 0d 0a 0d 0a 54 68 69 73 20 69 73 20 61 20 63 6c 65 61 72 2d 73 69   67 6e 65 64 20 6d 65 73 73 61 67 65 2e 0d 0a3.5.  Creating an Compressed-only Message   This section describes the format for compressing a MIME entity.   Please note that versions of S/MIME prior to 3.1 did not specify any   use of CompressedData, and will not recognize it.  The use of a   capability to indicate the ability to receive CompressedData is   described in [CMSCOMPR] and is the preferred method for   compatibility.   Step 1.  The MIME entity to be compressed is prepared according tosection 3.1.   Step 2.  The MIME entity and other required data is processed into a   CMS object of type CompressedData.   Step 3.  The CompressedData object is wrapped in a CMS ContentInfo   object.   Step 4.  The ContentInfo object is inserted into an   application/pkcs7-mime MIME entity.   The smime-type parameter for compressed-only messages is   "compressed-data".  The file extension for this type of message is   ".p7z".   A sample message would be:       Content-Type: application/pkcs7-mime; smime-type=compressed-data;            name=smime.p7z       Content-Transfer-Encoding: base64       Content-Disposition: attachment; filename=smime.p7z       rfvbnj756tbBghyHhHUujhJhjH77n8HHGT9HG4VQpfyF467GhIGfHfYT6       7n8HHGghyHhHUujhJh4VQpfyF467GhIGfHfYGTrfvbnjT6jH7756tbB9H       f8HHGTrfvhJhjH776tbB9HG4VQbnj7567GhIGfHfYT6ghyHhHUujpfyF4       0GhIGfHfQbnj756YT64VRamsdell                    Standards Track                    [Page 26]

RFC 3851 S/MIME 3.1 Message Specification July 20043.6. Multiple Operations The signed-only, encrypted-only, and compressed-only MIME formats can be nested. This works because these formats are all MIME entities that encapsulate other MIME entities. An S/MIME implementation MUST be able to receive and process arbitrarily nested S/MIME within reasonable resource limits of the recipient computer. It is possible to apply any of the signing, encrypting, and compressing operations in any order. It is up to the implementer and the user to choose. When signing first, the signatories are then securely obscured by the enveloping. When enveloping first the signatories are exposed, but it is possible to verify signatures without removing the enveloping. This can be useful in an environment were automatic signature verification is desired, as no private key material is required to verify a signature. There are security ramifications to choosing whether to sign first or encrypt first. A recipient of a message that is encrypted and then signed can validate that the encrypted block was unaltered, but cannot determine any relationship between the signer and the unencrypted contents of the message. A recipient of a message that is signed-then-encrypted can assume that the signed message itself has not been altered, but that a careful attacker could have changed the unauthenticated portions of the encrypted message. When using compression, keep the following guidelines in mind: - Compression of binary encoded encrypted data is discouraged, since it will not yield significant compression. Base64 encrypted data could very well benefit, however. - If a lossy compression algorithm is used with signing, you will need to compress first, then sign.3.7. Creating a Certificate Management Message The certificate management message or MIME entity is used to transport certificates and/or certificate revocation lists, such as in response to a registration request. Step 1. The certificates and/or certificate revocation lists are made available to the CMS generating process which creates a CMS object of type SignedData. The SignedData encapContentInfo eContent field MUST be absent and signerInfos field MUST be empty.Ramsdell Standards Track [Page 27]

RFC 3851 S/MIME 3.1 Message Specification July 2004 Step 2. The SignedData object is wrapped in a CMS ContentInfo object. Step 3. The ContentInfo object is enclosed in an application/pkcs7- mime MIME entity. The smime-type parameter for a certificate management message is "certs-only". The file extension for this type of message is ".p7c".3.8. Registration Requests A sending agent that signs messages MUST have a certificate for the signature so that a receiving agent can verify the signature. There are many ways of getting certificates, such as through an exchange with a certificate authority, through a hardware token or diskette, and so on. S/MIME v2 [SMIMEV2] specified a method for "registering" public keys with certificate authorities using an application/pkcs10 body part. Since that time, the IETF PKIX Working Group has developed other methods for requesting certificates. However, S/MIME v3.1 does not require a particular certificate request mechanism.3.9. Identifying an S/MIME Message Because S/MIME takes into account interoperation in non-MIME environments, several different mechanisms are employed to carry the type information, and it becomes a bit difficult to identify S/MIME messages. The following table lists criteria for determining whether or not a message is an S/MIME message. A message is considered an S/MIME message if it matches any of the criteria listed below. The file suffix in the table below comes from the "name" parameter in the content-type header, or the "filename" parameter on the content- disposition header. These parameters that give the file suffix are not listed below as part of the parameter section. MIME type: application/pkcs7-mime parameters: any file suffix: any MIME type: multipart/signed parameters: protocol="application/pkcs7-signature" file suffix: any MIME type: application/octet-stream parameters: any file suffix: p7m, p7s, p7c, p7zRamsdell Standards Track [Page 28]

RFC 3851            S/MIME 3.1 Message Specification           July 20044.  Certificate Processing   A receiving agent MUST provide some certificate retrieval mechanism   in order to gain access to certificates for recipients of digital   envelopes.  This specification does not cover how S/MIME agents   handle certificates, only what they do after a certificate has been   validated or rejected.  S/MIME certificate issues are covered in   [CERT31].   At a minimum, for initial S/MIME deployment, a user agent could   automatically generate a message to an intended recipient requesting   that recipient's certificate in a signed return message.  Receiving   and sending agents SHOULD also provide a mechanism to allow a user to   "store and protect" certificates for correspondents in such a way so   as to guarantee their later retrieval.4.1.  Key Pair Generation   All generated key pairs MUST be generated from a good source of non-   deterministic random input [RANDOM] and the private key MUST be   protected in a secure fashion.   If an S/MIME agent needs to generate an RSA key pair, then the S/MIME   agent or some related administrative utility or function SHOULD   generate RSA key pairs using the following guidelines.  A user agent   SHOULD generate RSA key pairs at a minimum key size of 768 bits.  A   user agent MUST NOT generate RSA key pairs less than 512 bits long.   Creating keys longer than 1024 bits can cause some older S/MIME   receiving agents to not be able to verify signatures, but gives   better security and is therefore valuable.  A receiving agent SHOULD   be able to verify signatures with keys of any size over 512 bits.   Some agents created in the United States have chosen to create 512   bit keys in order to get more advantageous export licenses.  However,   512 bit keys are considered by many to be cryptographically insecure.   Implementers SHOULD be aware that multiple (active) key pairs can be   associated with a single individual.  For example, one key pair can   be used to support confidentiality, while a different key pair can be   used for authentication.5.  Security Considerations   40-bit encryption is considered weak by most cryptographers.  Using   weak cryptography in S/MIME offers little actual security over   sending plaintext.  However, other features of S/MIME, such as the   specification of tripleDES and the ability to announce stronger   cryptographic capabilities to parties with whom you communicate,   allow senders to create messages that use strong encryption.  Using   weak cryptography is never recommended unless the only alternative isRamsdell                    Standards Track                    [Page 29]

RFC 3851 S/MIME 3.1 Message Specification July 2004 no cryptography. When feasible, sending and receiving agents SHOULD inform senders and recipients of the relative cryptographic strength of messages. It is impossible for most software or people to estimate the value of a message. Further, it is impossible for most software or people to estimate the actual cost of decrypting a message that is encrypted with a key of a particular size. Further, it is quite difficult to determine the cost of a failed decryption if a recipient cannot decode a message. Thus, choosing between different key sizes (or choosing whether to just use plaintext) is also impossible. However, decisions based on these criteria are made all the time, and therefore this specification gives a framework for using those estimates in choosing algorithms. If a sending agent is sending the same message using different strengths of cryptography, an attacker watching the communications channel might be able to determine the contents of the strongly- encrypted message by decrypting the weakly-encrypted version. In other words, a sender SHOULD NOT send a copy of a message using weaker cryptography than they would use for the original of the message. Modification of the ciphertext can go undetected if authentication is not also used, which is the case when sending EnvelopedData without wrapping it in SignedData or enclosing SignedData within it. SeeRFC 3218 [MMA] for more information about thwarting the adaptive chosen ciphertext vulnerability in PKCS #1 Version 1.5 implementations. In some circumstances the use of the Diffie-Hellman key agreement scheme in a prime order subgroup of a large prime p is vulnerable to certain attacks known as "small-subgroup" attacks. Methods exist, however, to prevent these attacks. These methods are described inRFC 2785 [DHSUB].Ramsdell Standards Track [Page 30]

RFC 3851            S/MIME 3.1 Message Specification           July 2004A.  ASN.1 ModuleSecureMimeMessageV3dot1  { iso(1) member-body(2) us(840) rsadsi(113549)         pkcs(1) pkcs-9(9) smime(16) modules(0) msg-v3dot1(21) }DEFINITIONS IMPLICIT TAGS ::=BEGINIMPORTS-- Cryptographic Message Syntax    SubjectKeyIdentifier, IssuerAndSerialNumber,    RecipientKeyIdentifier        FROM    CryptographicMessageSyntax               { iso(1) member-body(2) us(840) rsadsi(113549)                 pkcs(1) pkcs-9(9) smime(16) modules(0) cms-2001(14) };--  id-aa is the arc with all new authenticated and unauthenticated--  attributes produced the by S/MIME Working Groupid-aa OBJECT IDENTIFIER ::= {iso(1) member-body(2) usa(840)        rsadsi(113549) pkcs(1) pkcs-9(9) smime(16) attributes(2)}-- S/MIME Capabilities provides a method of broadcasting the symmetric-- capabilities understood.  Algorithms SHOULD be ordered by-- preference and grouped by typesmimeCapabilities OBJECT IDENTIFIER ::=   {iso(1) member-body(2) us(840) rsadsi(113549) pkcs(1) pkcs-9(9) 15}SMIMECapability ::= SEQUENCE {   capabilityID OBJECT IDENTIFIER,   parameters ANY DEFINED BY capabilityID OPTIONAL }SMIMECapabilities ::= SEQUENCE OF SMIMECapability-- Encryption Key Preference provides a method of broadcasting the-- preferred encryption certificate.id-aa-encrypKeyPref OBJECT IDENTIFIER ::= {id-aa 11}SMIMEEncryptionKeyPreference ::= CHOICE {   issuerAndSerialNumber   [0] IssuerAndSerialNumber,   receipentKeyId          [1] RecipientKeyIdentifier,   subjectAltKeyIdentifier [2] SubjectKeyIdentifier}Ramsdell                    Standards Track                    [Page 31]

RFC 3851            S/MIME 3.1 Message Specification           July 2004id-smime OBJECT IDENTIFIER ::= { iso(1) member-body(2)   us(840) rsadsi(113549) pkcs(1) pkcs9(9) 16 }id-cap  OBJECT IDENTIFIER ::= { id-smime 11 }-- The preferBinaryInside indicates an ability to receive messages-- with binary encoding inside the CMS wrapperid-cap-preferBinaryInside  OBJECT IDENTIFIER ::= { id-cap 1 }--  The following list the OIDs to be used with S/MIME V3-- Signature Algorithms Not Found in [CMSALG]---- md2WithRSAEncryption OBJECT IDENTIFIER ::=--    {iso(1) member-body(2) us(840) rsadsi(113549) pkcs(1) pkcs-1(1)--     2}---- Other Signed Attributes---- signingTime OBJECT IDENTIFIER ::=--    {iso(1) member-body(2) us(840) rsadsi(113549) pkcs(1) pkcs-9(9)--     5}--    See [CMS] for a description of how to encode the attribute--    value.SMIMECapabilitiesParametersForRC2CBC ::= INTEGER--        (RC2 Key Length (number of bits))ENDB.  ReferencesB.1.  Normative References   [CERT31]      Ramsdell, B., Ed., "S/MIME Version 3.1 Certificate                 Handling",RFC 3850, July 2004.   [CHARSETS]    Character sets assigned by IANA.  Seehttp://www.iana.org/assignments/character-sets   [CMS]         Housley, R., "Cryptographic Message Syntax (CMS)",RFC3852, July 2004.   [CMSAES]      Schaad, J., "Use of the Advanced Encryption Standard                 (AES) Encryption Algorithm in Cryptographic Message                 Syntax (CMS)",RFC 3565, July 2003.Ramsdell                    Standards Track                    [Page 32]

RFC 3851            S/MIME 3.1 Message Specification           July 2004   [CMSALG]      Housley, R., "Cryptographic Message Syntax (CMS)                 Algorithms",RFC 3370, August 2002.   [CMSCOMPR]    Gutmann, P., "Compressed Data Content Type for                 Cryptographic Message Syntax (CMS)",RFC 3274, June                 2002.   [CONTDISP]    Troost, R., Dorner, S., and K. Moore, "Communicating                 Presentation Information in Internet Messages: The                 Content-Disposition Header Field",RFC 2183, August                 1997.   [ESS]         Hoffman, P., "Enhanced Security Services for S/MIME",RFC 2634, June 1999.   [FIPS180-2]   "Secure Hash Signature Standard (SHS)", National                 Institute of Standards and Technology (NIST).  FIPS                 Publication 180-2.   [MIME-SPEC]   Freed, N. and N. Borenstein, "Multipurpose Internet                 Mail Extensions (MIME) Part One: Format of Internet                 Message Bodies",RFC 2045, November 1996.                 Freed, N. and N. Borenstein, "Multipurpose Internet                 Mail Extensions (MIME) Part Two: Media Types",RFC2046, November 1996.                 Moore, K., "MIME (Multipurpose Internet Mail                 Extensions) Part Three:  Message Header Extensions for                 Non-ASCII Text",RFC 2047, November 1996.                 Freed, N., Klensin, J., and J. Postel, "Multipurpose                 Internet Mail Extensions (MIME) Part Four: Registration                 Procedures",BCP 13,RFC 2048, November 1996.                 Freed, N. and N. Borenstein, "Multipurpose Internet                 Mail Extensions (MIME) Part Five: Conformance Criteria                 and Examples",RFC 2049, November 1996.   [MIME-SECURE] Galvin, J., Murphy, S., Crocker, S., and N. Freed,                 "Security Multiparts for MIME: Multipart/Signed and                 Multipart/Encrypted",RFC 1847, October 1995.   [MUSTSHOULD]  Bradner, S., "Key words for use in RFCs to Indicate                 Requirement Levels",BCP 14,RFC 2119, March 1997.   [X.208-88]    CCITT.  Recommendation X.208: Specification of Abstract                 Syntax Notation One (ASN.1).  1988.Ramsdell                    Standards Track                    [Page 33]

RFC 3851            S/MIME 3.1 Message Specification           July 2004   [X.209-88]    CCITT.  Recommendation X.209: Specification of Basic                 Encoding Rules for Abstract Syntax Notation One                 (ASN.1).  1988.   [X.509-88]    CCITT.  Recommendation X.509: The Directory -                 Authentication Framework.  1988.B.2.  Informative References   [DHSUB]       Zuccherato, R., "Methods for Avoiding the "Small-                 Subgroup" Attacks on the Diffie-Hellman Key Agreement                 Method for S/MIME",RFC 2785, March 2000.   [MMA]         Rescorla, E., "Preventing the Million Message Attack on                 Cryptographic Message Syntax",RFC 3218, January 2002.   [PKCS-7]      Kaliski, B., "PKCS #7: Cryptographic Message Syntax                 Version 1.5",RFC 2315, March 1998.   [RANDOM]      Eastlake 3rd, D., Crocker, S., and J. Schiller,                 "Randomness Recommendations for Security",RFC 1750,                 December 1994.   [SMIMEV2]     Dusse, S., Hoffman, P., Ramsdell, B., Lundblade, L.,                 and L. Repka, "S/MIME Version 2 Message Specification",RFC 2311, March 1998.Ramsdell                    Standards Track                    [Page 34]

RFC 3851            S/MIME 3.1 Message Specification           July 2004C.  Acknowledgements   Many thanks go out to the other authors of the S/MIME Version 2   Message Specification RFC: Steve Dusse, Paul Hoffman, Laurence   Lundblade and Lisa Repka.   A number of the members of the S/MIME Working Group have also worked   very hard and contributed to this document.  Any list of people is   doomed to omission, and for that I apologize.  In alphabetical order,   the following people stand out in my mind due to the fact that they   made direct contributions to this document.   Tony Capel   Piers Chivers   Dave Crocker   Bill Flanigan   Peter Gutmann   Paul Hoffman   Russ Housley   William Ottaway   John Pawling   Jim SchaadD.  Editor's Address   Blake Ramsdell   Sendmail, Inc.   704 228th Ave NE #775   Sammamish, WA  98074   EMail: blake@sendmail.comRamsdell                    Standards Track                    [Page 35]

RFC 3851            S/MIME 3.1 Message Specification           July 2004Full Copyright Statement   Copyright (C) The Internet Society (2004).  This document is subject   to the rights, licenses and restrictions contained inBCP 78, and   except as set forth therein, the authors retain all their rights.   This document and the information contained herein are provided on an   "AS IS" basis and THE CONTRIBUTOR, THE ORGANIZATION HE/SHE REPRESENTS   OR IS SPONSORED BY (IF ANY), THE INTERNET SOCIETY AND THE INTERNET   ENGINEERING TASK FORCE DISCLAIM ALL WARRANTIES, EXPRESS OR IMPLIED,   INCLUDING BUT NOT LIMITED TO ANY WARRANTY THAT THE USE OF THE   INFORMATION HEREIN WILL NOT INFRINGE ANY RIGHTS OR ANY IMPLIED   WARRANTIES OF MERCHANTABILITY OR FITNESS FOR A PARTICULAR PURPOSE.Intellectual Property   The IETF takes no position regarding the validity or scope of any   Intellectual Property Rights or other rights that might be claimed to   pertain to the implementation or use of the technology described in   this document or the extent to which any license under such rights   might or might not be available; nor does it represent that it has   made any independent effort to identify any such rights.  Information   on the procedures with respect to rights in RFC documents can be   found inBCP 78 andBCP 79.   Copies of IPR disclosures made to the IETF Secretariat and any   assurances of licenses to be made available, or the result of an   attempt made to obtain a general license or permission for the use of   such proprietary rights by implementers or users of this   specification can be obtained from the IETF on-line IPR repository athttp://www.ietf.org/ipr.   The IETF invites any interested party to bring to its attention any   copyrights, patents or patent applications, or other proprietary   rights that may cover technology that may be required to implement   this standard.  Please address the information to the IETF at ietf-   ipr@ietf.org.Acknowledgement   Funding for the RFC Editor function is currently provided by the   Internet Society.Ramsdell                    Standards Track                    [Page 36]

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