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authorThomas Voss <mail@thomasvoss.com> 2024-11-27 20:54:24 +0100
committerThomas Voss <mail@thomasvoss.com> 2024-11-27 20:54:24 +0100
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+Internet Engineering Task Force (IETF) J. Schaad
+Request for Comments: 8551 August Cellars
+Obsoletes: 5751 B. Ramsdell
+Category: Standards Track Brute Squad Labs, Inc.
+ISSN: 2070-1721 S. Turner
+ sn3rd
+ April 2019
+
+
+ Secure/Multipurpose Internet Mail Extensions (S/MIME) Version 4.0
+ Message Specification
+
+Abstract
+
+ This document defines Secure/Multipurpose Internet Mail Extensions
+ (S/MIME) version 4.0. 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 obsoletes RFC 5751.
+
+Status of This Memo
+
+ This is an Internet Standards Track document.
+
+ This document is a product of the Internet Engineering Task Force
+ (IETF). It represents the consensus of the IETF community. It has
+ received public review and has been approved for publication by the
+ Internet Engineering Steering Group (IESG). Further information on
+ Internet Standards is available in Section 2 of RFC 7841.
+
+ Information about the current status of this document, any errata,
+ and how to provide feedback on it may be obtained at
+ https://www.rfc-editor.org/info/rfc8551.
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+Schaad, et al. Standards Track [Page 1]
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+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+Copyright Notice
+
+ Copyright (c) 2019 IETF Trust and the persons identified as the
+ document authors. All rights reserved.
+
+ This document is subject to BCP 78 and the IETF Trust's Legal
+ Provisions Relating to IETF Documents
+ (https://trustee.ietf.org/license-info) in effect on the date of
+ publication of this document. Please review these documents
+ carefully, as they describe your rights and restrictions with respect
+ to this document. Code Components extracted from this document must
+ include Simplified BSD License text as described in Section 4.e of
+ the Trust Legal Provisions and are provided without warranty as
+ described in the Simplified BSD License.
+
+ This document may contain material from IETF Documents or IETF
+ Contributions published or made publicly available before November
+ 10, 2008. The person(s) controlling the copyright in some of this
+ material may not have granted the IETF Trust the right to allow
+ modifications of such material outside the IETF Standards Process.
+ Without obtaining an adequate license from the person(s) controlling
+ the copyright in such materials, this document may not be modified
+ outside the IETF Standards Process, and derivative works of it may
+ not be created outside the IETF Standards Process, except to format
+ it for publication as an RFC or to translate it into languages other
+ than English.
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+Schaad, et al. Standards Track [Page 2]
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+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+Table of Contents
+
+ 1. Introduction . . . . . . . . . . . . . . . . . . . . . . . . 5
+ 1.1. Specification Overview . . . . . . . . . . . . . . . . . 5
+ 1.2. Definitions . . . . . . . . . . . . . . . . . . . . . . . 6
+ 1.3. Conventions Used in This Document . . . . . . . . . . . . 7
+ 1.4. Compatibility with Prior Practice of S/MIME . . . . . . . 8
+ 1.5. Changes from S/MIME v3 to S/MIME v3.1 . . . . . . . . . . 9
+ 1.6. Changes from S/MIME v3.1 to S/MIME v3.2 . . . . . . . . . 9
+ 1.7. Changes for S/MIME v4.0 . . . . . . . . . . . . . . . . . 11
+ 2. CMS Options . . . . . . . . . . . . . . . . . . . . . . . . . 12
+ 2.1. DigestAlgorithmIdentifier . . . . . . . . . . . . . . . . 12
+ 2.2. SignatureAlgorithmIdentifier . . . . . . . . . . . . . . 12
+ 2.3. KeyEncryptionAlgorithmIdentifier . . . . . . . . . . . . 13
+ 2.4. General Syntax . . . . . . . . . . . . . . . . . . . . . 13
+ 2.4.1. Data Content Type . . . . . . . . . . . . . . . . . . 14
+ 2.4.2. SignedData Content Type . . . . . . . . . . . . . . . 14
+ 2.4.3. EnvelopedData Content Type . . . . . . . . . . . . . 14
+ 2.4.4. AuthEnvelopedData Content Type . . . . . . . . . . . 14
+ 2.4.5. CompressedData Content Type . . . . . . . . . . . . . 14
+ 2.5. Attributes and the SignerInfo Type . . . . . . . . . . . 15
+ 2.5.1. Signing Time Attribute . . . . . . . . . . . . . . . 15
+ 2.5.2. SMIMECapabilities Attribute . . . . . . . . . . . . . 16
+ 2.5.3. Encryption Key Preference Attribute . . . . . . . . . 17
+ 2.6. SignerIdentifier SignerInfo Type . . . . . . . . . . . . 19
+ 2.7. ContentEncryptionAlgorithmIdentifier . . . . . . . . . . 19
+ 2.7.1. Deciding Which Encryption Method to Use . . . . . . . 19
+ 2.7.2. Choosing Weak Encryption . . . . . . . . . . . . . . 21
+ 2.7.3. Multiple Recipients . . . . . . . . . . . . . . . . . 21
+ 3. Creating S/MIME Messages . . . . . . . . . . . . . . . . . . 21
+ 3.1. Preparing the MIME Entity for Signing, Enveloping, or
+ Compressing . . . . . . . . . . . . . . . . . . . . . . . 22
+ 3.1.1. Canonicalization . . . . . . . . . . . . . . . . . . 23
+ 3.1.2. Transfer Encoding . . . . . . . . . . . . . . . . . . 24
+ 3.1.3. Transfer Encoding for Signing Using multipart/signed 25
+ 3.1.4. Sample Canonical MIME Entity . . . . . . . . . . . . 25
+ 3.2. The application/pkcs7-mime Media Type . . . . . . . . . . 26
+ 3.2.1. The name and filename Parameters . . . . . . . . . . 27
+ 3.2.2. The smime-type Parameter . . . . . . . . . . . . . . 28
+ 3.3. Creating an Enveloped-Only Message . . . . . . . . . . . 29
+ 3.4. Creating an Authenticated Enveloped-Only Message . . . . 30
+ 3.5. Creating a Signed-Only Message . . . . . . . . . . . . . 31
+ 3.5.1. Choosing a Format for Signed-Only Messages . . . . . 32
+ 3.5.2. Signing Using application/pkcs7-mime with SignedData 32
+ 3.5.3. Signing Using the multipart/signed Format . . . . . . 33
+ 3.6. Creating a Compressed-Only Message . . . . . . . . . . . 36
+ 3.7. Multiple Operations . . . . . . . . . . . . . . . . . . . 37
+ 3.8. Creating a Certificate Management Message . . . . . . . . 38
+
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+Schaad, et al. Standards Track [Page 3]
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+RFC 8551 S/MIME 4.0 Message Specification April 2019
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+ 3.9. Registration Requests . . . . . . . . . . . . . . . . . . 38
+ 3.10. Identifying an S/MIME Message . . . . . . . . . . . . . . 39
+ 4. Certificate Processing . . . . . . . . . . . . . . . . . . . 39
+ 4.1. Key Pair Generation . . . . . . . . . . . . . . . . . . . 40
+ 4.2. Signature Generation . . . . . . . . . . . . . . . . . . 40
+ 4.3. Signature Verification . . . . . . . . . . . . . . . . . 40
+ 4.4. Encryption . . . . . . . . . . . . . . . . . . . . . . . 41
+ 4.5. Decryption . . . . . . . . . . . . . . . . . . . . . . . 41
+ 5. IANA Considerations . . . . . . . . . . . . . . . . . . . . . 41
+ 5.1. Media Type for application/pkcs7-mime . . . . . . . . . . 42
+ 5.2. Media Type for application/pkcs7-signature . . . . . . . 43
+ 5.3. authEnveloped-data smime-type . . . . . . . . . . . . . . 44
+ 5.4. Reference Updates . . . . . . . . . . . . . . . . . . . . 44
+ 6. Security Considerations . . . . . . . . . . . . . . . . . . . 44
+ 7. References . . . . . . . . . . . . . . . . . . . . . . . . . 48
+ 7.1. Reference Conventions . . . . . . . . . . . . . . . . . . 48
+ 7.2. Normative References . . . . . . . . . . . . . . . . . . 49
+ 7.3. Informative References . . . . . . . . . . . . . . . . . 52
+ Appendix A. ASN.1 Module . . . . . . . . . . . . . . . . . . . . 57
+ Appendix B. Historic Mail Considerations . . . . . . . . . . . . 59
+ B.1. DigestAlgorithmIdentifier . . . . . . . . . . . . . . . . 59
+ B.2. Signature Algorithms . . . . . . . . . . . . . . . . . . 59
+ B.3. ContentEncryptionAlgorithmIdentifier . . . . . . . . . . 61
+ B.4. KeyEncryptionAlgorithmIdentifier . . . . . . . . . . . . 62
+ Appendix C. Moving S/MIME v2 Message Specification to Historic
+ Status . . . . . . . . . . . . . . . . . . . . . . . 62
+ Acknowledgements . . . . . . . . . . . . . . . . . . . . . . . . 62
+ Authors' Addresses . . . . . . . . . . . . . . . . . . . . . . . 63
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+Schaad, et al. Standards Track [Page 4]
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+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+1. 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). As a supplementary service, S/MIME provides message
+ compression.
+
+ 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 or SIP.
+ 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.
+
+ This document defines version 4.0 of the S/MIME Message
+ Specification. As such, this document obsoletes version 3.2 of the
+ S/MIME Message Specification [RFC5751].
+
+ This specification contains a number of references to documents that
+ have been obsoleted or replaced. This is intentional, as the updated
+ documents often do not have the same information or protocol
+ requirements in them.
+
+1.1. 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 of Internet messages and
+ allows extensions for new applications based on content-type.
+
+ This specification defines how to create a MIME body part that has
+ been cryptographically enhanced according to the Cryptographic
+ Message Syntax (CMS) [CMS], which is derived from PKCS #7 [RFC2315].
+ This specification also defines the application/pkcs7-mime media
+ type, which can be used to transport those body parts.
+
+
+
+
+
+Schaad, et al. Standards Track [Page 5]
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+RFC 8551 S/MIME 4.0 Message Specification April 2019
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+ This document also discusses how to use the multipart/signed media
+ type defined in [RFC1847] to transport S/MIME signed messages.
+ multipart/signed is used in conjunction with the
+ application/pkcs7-signature media 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 [CMS], [RFC3370], [RFC4056], [RFC3560], and [RFC5754].
+
+ 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 follow the Robustness Principle (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. Definitions
+
+ For the purposes of this specification, the following definitions
+ apply.
+
+ ASN.1:
+ Abstract Syntax Notation One, as defined in ITU-T Recommendations
+ X.680, X.681, X.682, and X.683 [ASN.1].
+
+ BER:
+ Basic Encoding Rules for ASN.1, as defined in ITU-T Recommendation
+ X.690 [X.690].
+
+ 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 ITU-T
+ Recommendation X.690 [X.690].
+
+
+
+Schaad, et al. Standards Track [Page 6]
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+RFC 8551 S/MIME 4.0 Message Specification April 2019
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+
+ 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.
+
+ Data integrity service:
+ A security service that protects against unauthorized changes to
+ data by ensuring that changes to the data are detectable
+ [RFC4949].
+
+ Data confidentiality:
+ The property that data is not disclosed to system entities unless
+ they have been authorized to know the data [RFC4949].
+
+1.3. Conventions Used in This Document
+
+ The key words "MUST", "MUST NOT", "REQUIRED", "SHALL", "SHALL NOT",
+ "SHOULD", "SHOULD NOT", "RECOMMENDED", "NOT RECOMMENDED", "MAY", and
+ "OPTIONAL" in this document are to be interpreted as described in
+ BCP 14 [RFC2119] [RFC8174] when, and only when, they appear in all
+ capitals, as shown here.
+
+
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+Schaad, et al. Standards Track [Page 7]
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+RFC 8551 S/MIME 4.0 Message Specification April 2019
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+ We define the additional requirement levels:
+
+ SHOULD+ This term means the same as SHOULD. However, the authors
+ expect that a requirement marked as SHOULD+ will be
+ promoted at some future time to be a MUST.
+
+ SHOULD- This term means the same as SHOULD. However, the authors
+ expect that a requirement marked as SHOULD- will be demoted
+ to a MAY in a future version of this document.
+
+ MUST- This term means the same as MUST. However, the authors
+ expect that this requirement will no longer be a MUST in a
+ future document. Although its status will be determined at
+ a later time, it is reasonable to expect that if a future
+ revision of a document alters the status of a MUST-
+ requirement, it will remain at least a SHOULD or a SHOULD-.
+
+ The term "RSA" in this document almost always refers to the
+ PKCS #1 v1.5 RSA [RFC2313] signature or encryption algorithms even
+ when not qualified as such. There are a couple of places where it
+ refers to the general RSA cryptographic operation; these can be
+ determined from the context where it is used.
+
+1.4. Compatibility with Prior Practice of S/MIME
+
+ S/MIME version 4.0 agents ought to attempt to have the greatest
+ interoperability possible with agents for prior versions of S/MIME.
+
+ - S/MIME version 2 is described in RFC 2311 through RFC 2315
+ inclusive [SMIMEv2].
+
+ - S/MIME version 3 is described in RFC 2630 through RFC 2634
+ inclusive and RFC 5035 [SMIMEv3].
+
+ - S/MIME version 3.1 is described in RFC 2634, RFC 3850, RFC 3851,
+ RFC 3852, and RFC 5035 [SMIMEv3.1].
+
+ - S/MIME version 3.2 is described in RFC 2634, RFC 5035, RFC 5652,
+ RFC 5750, and RFC 5751 [SMIMEv3.2].
+
+ - [RFC2311] also has historical information about the development of
+ S/MIME.
+
+
+
+
+
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+Schaad, et al. Standards Track [Page 8]
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+RFC 8551 S/MIME 4.0 Message Specification April 2019
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+1.5. Changes from S/MIME v3 to S/MIME v3.1
+
+ This section describes the changes made between S/MIME v3 and
+ S/MIME v3.1. Note that the requirement levels indicated by the
+ capitalized key words ("MUST", "SHOULD", etc.) may have changed in
+ later versions of S/MIME.
+
+ - The RSA public key algorithm was changed to a MUST implement. The
+ key wrap algorithm and the Diffie-Hellman (DH) algorithm [RFC2631]
+ were 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 media type
+ has been added.
+
+ - Use of the CompressedData CMS type is allowed, along with required
+ media type and file extension additions.
+
+1.6. Changes from S/MIME v3.1 to S/MIME v3.2
+
+ This section describes the changes made between S/MIME v3.1 and
+ S/MIME v3.2. Note that the requirement levels indicated by the
+ capitalized key words ("MUST", "SHOULD", etc.) may have changed in
+ later versions of S/MIME. Note that the section numbers listed here
+ (e.g., 3.4.3.2) are from [RFC5751].
+
+ - Made editorial changes, e.g., replaced "MIME type" with "media
+ type", "content-type" with "Content-Type".
+
+ - Moved "Conventions Used in This Document" to Section 1.3. Added
+ definitions for SHOULD+, SHOULD-, and MUST-.
+
+ - Section 1.1 and Appendix A: Added references to RFCs for
+ RSASSA-PSS, RSAES-OAEP, and SHA2 CMS algorithms. Added CMS
+ Multiple Signers Clarification to CMS reference.
+
+
+
+
+Schaad, et al. Standards Track [Page 9]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
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+
+ - Section 1.2: Updated references to ASN.1 to X.680, and BER and DER
+ to X.690.
+
+ - Section 1.4: Added references to S/MIME v3.1 RFCs.
+
+ - Section 2.1 (digest algorithm): SHA-256 added as MUST, SHA-1 and
+ MD5 made SHOULD-.
+
+ - Section 2.2 (signature algorithms): RSA with SHA-256 added as
+ MUST; DSA with SHA-256 added as SHOULD+; RSA with SHA-1, DSA with
+ SHA-1, and RSA with MD5 changed to SHOULD-; and RSASSA-PSS with
+ SHA-256 added as SHOULD+. Also added note about what S/MIME v3.1
+ clients support.
+
+ - Section 2.3 (key encryption): DH changed to SHOULD-, and RSAES-
+ OAEP added as SHOULD+. Elaborated on requirements for key wrap
+ algorithm.
+
+ - Section 2.5.1: Added requirement that receiving agents MUST
+ support both GeneralizedTime and UTCTime.
+
+ - Section 2.5.2: Replaced reference "sha1WithRSAEncryption" with
+ "sha256WithRSAEncryption", replaced "DES-3EDE-CBC" with "AES-128
+ CBC", and deleted the RC5 example.
+
+ - Section 2.5.2.1: Deleted entire section (discussed
+ deprecated RC2).
+
+ - Section 2.7, Section 2.7.1, and Appendix A: References to RC2/40
+ removed.
+
+ - Section 2.7 (content encryption): AES-128 CBC added as MUST,
+ AES-192 and AES-256 CBC SHOULD+, and tripleDES now SHOULD-.
+
+ - Section 2.7.1: Updated pointers from 2.7.2.1 through 2.7.2.4 to
+ 2.7.1.1 and 2.7.1.2.
+
+ - Section 3.1.1: Removed text about MIME character sets.
+
+ - Sections 3.2.2 and 3.6: Replaced "encrypted" with "enveloped".
+ Updated OID example to use AES-128 CBC OID.
+
+ - Section 3.4.3.2: Replaced "micalg" parameter for "SHA-1" with
+ "sha-1".
+
+ - Section 4: Updated reference to CERT v3.2.
+
+
+
+
+
+Schaad, et al. Standards Track [Page 10]
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+RFC 8551 S/MIME 4.0 Message Specification April 2019
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+
+ - Section 4.1: Updated RSA and DSA key size discussion. Moved last
+ four sentences to security considerations. Updated reference to
+ randomness requirements for security.
+
+ - Section 5: Added IANA registration templates to update media type
+ registry to point to this document as opposed to RFC 2311.
+
+ - Section 6: Updated security considerations.
+
+ - Section 7: Moved references from Appendix B to this section.
+ Updated references. Added informative references to SMIMEv2,
+ SMIMEv3, and SMIMEv3.1.
+
+ - Appendix B: Added Appendix B to move S/MIME v2 to Historic status.
+
+1.7. Changes for S/MIME v4.0
+
+ This section describes the changes made between S/MIME v3.2 and
+ S/MIME v4.0.
+
+ - Added the use of AuthEnvelopedData, including defining and
+ registering an smime-type value (Sections 2.4.4 and 3.4).
+
+ - Updated the content-encryption algorithms (Sections 2.7 and
+ 2.7.1.2): added AES-256 Galois/Counter Mode (GCM), added
+ ChaCha20-Poly1305, removed mention of AES-192 Cipher Block
+ Chaining (CBC), and marked tripleDES as historic.
+
+ - Updated the set of signature algorithms (Section 2.2): added the
+ Edwards-curve Digital Signature Algorithm (EdDSA), added the
+ Elliptic Curve Digital Signature Algorithm (ECDSA), and marked DSA
+ as historic.
+
+ - Updated the set of digest algorithms (Section 2.1): added SHA-512,
+ and marked SHA-1 as historic.
+
+ - Updated the size of keys to be used for RSA encryption and RSA
+ signing (Section 4).
+
+ - Created Appendix B, which discusses considerations for dealing
+ with historic email messages.
+
+
+
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+
+
+2. CMS Options
+
+ CMS allows for a wide variety of options in content, attributes, 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. [RFC3370] and
+ [RFC5754] provide additional details regarding the use of the
+ cryptographic algorithms. [ESS] provides additional details
+ regarding the use of additional attributes.
+
+2.1. DigestAlgorithmIdentifier
+
+ The algorithms here are used for digesting the body of the message
+ and are not the same as the digest algorithms used as part of the
+ signature algorithms. The result of this is placed in the
+ message-digest attribute of the signed attributes. It is RECOMMENDED
+ that the algorithm used for digesting the body of the message be of
+ similar strength to, or greater strength than, the signature
+ algorithm.
+
+ Sending and receiving agents:
+
+ - MUST support SHA-256.
+
+ - MUST support SHA-512.
+
+ [RFC5754] provides the details for using these algorithms with
+ S/MIME.
+
+2.2. SignatureAlgorithmIdentifier
+
+ There are different sets of requirements placed on receiving and
+ sending agents. By having the different requirements, the maximum
+ amount of interoperability is achieved, as it allows for specialized
+ protection of private key material but maximum signature validation.
+
+ Receiving agents:
+
+ - MUST support ECDSA with curve P-256 and SHA-256.
+
+ - MUST support EdDSA with curve25519 using PureEdDSA mode [RFC8419].
+
+ - MUST- support RSA PKCS #1 v1.5 with SHA-256.
+
+ - SHOULD support the RSA Probabilistic Signature Scheme (RSASSA-PSS)
+ with SHA-256.
+
+
+
+
+
+Schaad, et al. Standards Track [Page 12]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ Sending agents:
+
+ - MUST support at least one of the following algorithms: ECDSA with
+ curve P-256 and SHA-256, or EdDSA with curve25519 using PureEdDSA
+ mode.
+
+ - MUST- support RSA PKCS #1 v1.5 with SHA-256.
+
+ - SHOULD support RSASSA-PSS with SHA-256.
+
+ See Section 4.1 for information on key size and algorithm references.
+
+2.3. KeyEncryptionAlgorithmIdentifier
+
+ Receiving and sending agents:
+
+ - MUST support Elliptic Curve Diffie-Hellman (ECDH) ephemeral-static
+ mode for P-256, as specified in [RFC5753].
+
+ - MUST support ECDH ephemeral-static mode for X25519 using HKDF-256
+ ("HKDF" stands for "HMAC-based Key Derivation Function") for the
+ KDF, as specified in [RFC8418].
+
+ - MUST- support RSA encryption, as specified in [RFC3370].
+
+ - SHOULD+ support RSA Encryption Scheme - Optimal Asymmetric
+ Encryption Padding (RSAES-OAEP), as specified in [RFC3560].
+
+ When ECDH ephemeral-static is used, a key wrap algorithm is also
+ specified in the KeyEncryptionAlgorithmIdentifier [RFC5652]. The
+ underlying encryption functions for the key wrap and content-
+ encryption algorithms [RFC3370] [RFC3565] and the key sizes for the
+ two algorithms MUST be the same (e.g., AES-128 key wrap algorithm
+ with AES-128 content-encryption algorithm). As both 128-bit and
+ 256-bit AES modes are mandatory to implement as content-encryption
+ algorithms (Section 2.7), both the AES-128 and AES-256 key wrap
+ algorithms MUST be supported when ECDH ephemeral-static is used.
+ Recipients MAY enforce this but MUST use the weaker of the two as
+ part of any cryptographic strength computations they might do.
+
+ Appendix B provides information on algorithm support in older
+ versions of S/MIME.
+
+2.4. General Syntax
+
+ There are several CMS content types. Of these, only the Data,
+ SignedData, EnvelopedData, AuthEnvelopedData, and CompressedData
+ content types are currently used for S/MIME.
+
+
+
+Schaad, et al. Standards Track [Page 13]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+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 (OID), and the media type 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, per
+ Section 3.5.3 of this document). As another example, when applying
+ encryption to MIME data, the CMS EnvelopedData encryptedContentInfo
+ contentType MUST include the id-data OID 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.
+ In order to distribute the symmetric key, a sender needs to have
+ access to a public key for each intended message recipient to use
+ this service.
+
+2.4.4. AuthEnvelopedData Content Type
+
+ This content type is used to apply data confidentiality and message
+ integrity to a message. This content type does not provide
+ authentication or non-repudiation. In order to distribute the
+ symmetric key, a sender needs to have access to a public key for each
+ intended message recipient to use this service.
+
+2.4.5. 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; it is only used to reduce
+ the message's size.
+
+ See Section 3.7 for further guidance on the use of this type in
+ conjunction with other CMS types.
+
+
+
+
+Schaad, et al. Standards Track [Page 14]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+2.5. Attributes and the SignerInfo Type
+
+ The SignerInfo type allows the inclusion of unsigned and signed
+ attributes along with a signature. These attributes can be required
+ for the processing of messages (e.g., message digest), information
+ the signer supplied (e.g., SMIME capabilities) that should be
+ processed, or attributes that are not relevant to the current
+ situation (e.g., mlExpansionHistory [RFC2634] for mail viewers).
+
+ 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:
+
+ - Signing time (Section 2.5.1 in this document)
+
+ - SMIME capabilities (Section 2.5.2 in this document)
+
+ - Encryption key Preference (Section 2.5.3 in this document)
+
+ - Message digest (Section 11.2 in [RFC5652])
+
+ - Content type (Section 11.1 in [RFC5652])
+
+ Further, receiving agents SHOULD be able to handle zero or one
+ instance of the signingCertificate and signingCertificateV2 signed
+ attributes, as defined in Section 5 of RFC 2634 [ESS] and Section 3
+ of RFC 5035 [ESS], respectively.
+
+ Sending agents SHOULD generate one instance of the signingCertificate
+ or signingCertificateV2 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 they do 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 signingTime attribute is used to convey the time that a message
+ was signed. The time of signing will most likely be created by a
+ signer and therefore is only as trustworthy as that signer.
+
+
+
+
+
+Schaad, et al. Standards Track [Page 15]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ 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.
+
+ Receiving agents MUST be able to process signingTime attributes that
+ are encoded in either UTCTime or GeneralizedTime.
+
+2.5.2. SMIMECapabilities Attribute
+
+ The SMIMECapabilities attribute includes signature algorithms (such
+ as "sha256WithRSAEncryption"), symmetric algorithms (such as "AES-128
+ CBC"), authenticated symmetric algorithms (such as "AES-128 GCM"),
+ and key encipherment algorithms (such as "rsaEncryption"). The
+ presence of an SMIMECapability attribute containing an algorithm
+ implies that the sender can deal with the algorithm as well as
+ understand the ASN.1 structures associated with that algorithm.
+ There are also several identifiers that indicate support for other
+ optional features such as binary encoding and compression. The
+ SMIMECapabilities attribute was 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. CMS defines SignedAttributes as a SET OF Attribute.
+ The SignedAttributes in a signerInfo MUST include a single instance
+ of the SMIMECapabilities attribute. CMS defines the ASN.1 syntax for
+ Attribute to include attrValues SET OF AttributeValue. An
+ SMIMECapabilities attribute MUST only include a single instance of
+ AttributeValue. If a signature is detected as violating these
+ requirements, the signature SHOULD be treated as failing.
+
+ 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 it need not list all its capabilities so that the
+ capabilities list doesn't get too long. In an SMIMECapabilities
+ attribute, the 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.).
+
+
+
+
+
+
+Schaad, et al. Standards Track [Page 16]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ The structure of the SMIMECapabilities attribute is to facilitate
+ simple table lookups and binary comparisons in order to determine
+ matches. For instance, the encoding for the SMIMECapability for
+ sha256WithRSAEncryption includes rather than omits the NULL
+ parameter. 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.
+
+ The same OID that is used to identify an algorithm SHOULD also be
+ used in the SMIMECapability for that algorithm. There are cases
+ where a single OID can correspond to multiple algorithms. In these
+ cases, a single algorithm MUST be assigned to the SMIMECapability
+ using that OID. Additional OIDs from the smimeCapabilities OID tree
+ are then allocated for the other algorithms usages. 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. Additional values for
+ the SMIMECapabilities attribute might be defined in the future.
+ Receiving agents MUST handle an SMIMECapabilities object that has
+ values that it does not recognize in a graceful manner.
+
+ Section 2.7.1 explains a strategy for caching capabilities.
+
+2.5.3. 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.
+
+
+
+Schaad, et al. Standards Track [Page 17]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ If present, the SMIMEEncryptionKeyPreference attribute MUST be a
+ SignedAttribute. CMS defines SignedAttributes as a SET OF Attribute.
+ The SignedAttributes in a signerInfo MUST include a single instance
+ of the SMIMEEncryptionKeyPreference attribute. CMS defines the ASN.1
+ syntax for Attribute to include attrValues SET OF AttributeValue. An
+ SMIMEEncryptionKeyPreference attribute MUST only include a single
+ instance of AttributeValue. If a signature is detected as violating
+ these requirements, the signature SHOULD be treated as failing.
+
+ 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 encryption
+ 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 an X.509 certificate
+ with the same subject name as the signer of an X.509 certificate
+ that can be used for key management.
+
+
+
+
+
+
+
+Schaad, et al. Standards Track [Page 18]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ - Or, use some other method of determining the user's key management
+ key. If an 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 v4.0 implementations MUST support both issuerAndSerialNumber
+ and 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 each
+ matching certificate during signature verification before indicating
+ an error condition.
+
+2.7. ContentEncryptionAlgorithmIdentifier
+
+ Sending and receiving agents:
+
+ - MUST support encryption and decryption with AES-128 GCM and
+ AES-256 GCM [RFC5084].
+
+ - MUST- support encryption and decryption with AES-128 CBC
+ [RFC3565].
+
+ - SHOULD+ support encryption and decryption with ChaCha20-Poly1305
+ [RFC7905].
+
+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.
+
+
+
+
+Schaad, et al. Standards Track [Page 19]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ - 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 the
+ message. If the sending agent decides that weak encryption is
+ unacceptable for this data, then the sending agent MUST NOT use a
+ weak algorithm. The decision to use or not use weak encryption
+ overrides any other decision in this section about which encryption
+ algorithm to use.
+
+ Sections 2.7.1.1 and 2.7.1.2 describe the decisions a sending agent
+ SHOULD use when choosing 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 SHOULD use
+ AES-256 GCM, as AES-256 GCM is a stronger algorithm and is required
+ by S/MIME v4.0:
+
+
+
+
+Schaad, et al. Standards Track [Page 20]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ - The sending agent has no knowledge of the encryption capabilities
+ of the recipient.
+
+ - The sending agent has no knowledge of the version of S/MIME used
+ or supported by the recipient.
+
+ If the sending agent chooses not to use AES-256 GCM in this step,
+ given the presumption is that a client implementing AES-GCM would do
+ both AES-256 and AES-128, it SHOULD use AES-128 CBC.
+
+2.7.2. Choosing Weak Encryption
+
+ Algorithms such as RC2 are considered to be weak encryption
+ algorithms. Algorithms such as TripleDES are not state of the art
+ and are considered to be weaker algorithms than AES. A sending agent
+ that is controlled by a human SHOULD allow a human sender to
+ determine the risks of sending data using a weaker encryption
+ algorithm before sending the data, and possibly allow the human to
+ use a stronger encryption algorithm such as AES GCM or AES CBC even
+ if there is a possibility that the recipient will not be able to
+ process that algorithm.
+
+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 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 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 media 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 that
+ produce a CMS object. Finally, the CMS object is wrapped in MIME.
+ The "Enhanced Security Services for S/MIME" documents [ESS] provide
+ 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.
+
+
+
+
+Schaad, et al. Standards Track [Page 21]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ 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.
+
+ Anyone reading this section is expected to understand MIME as
+ described in [MIME-SPEC] and [RFC1847].
+
+3.1. Preparing the MIME Entity for Signing, Enveloping, or Compressing
+
+ S/MIME is used to secure MIME entities. A MIME message is composed
+ of a MIME header and a MIME body. A body can consist of a single
+ MIME entity or a tree of MIME entities (rooted with a multipart).
+ S/MIME can be used to secure either a single MIME entity or a tree of
+ MIME entities. These entities can be in locations other than the
+ root. S/MIME can be applied multiple times to different entities in
+ a single message. A MIME entity that is the whole message includes
+ only the MIME message headers and MIME body and does not include the
+ rfc822 header. Note that S/MIME can also be used to secure MIME
+ entities used in applications other than Internet mail. For cases
+ where protection of the rfc822 header is required, the use of the
+ message/rfc822 media 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 EnvelopedData,
+ CompressedData, and AuthEnvelopedData content types is described in
+ Sections 3.2 and 3.5. Other documents define additional CMS content
+ types; those documents should be consulted for processing those CMS
+ content types.
+
+ The procedure for preparing a MIME entity is given in [MIME-SPEC].
+ The same procedure is used here with some additional restrictions
+ when signing. The description of the procedures from [MIME-SPEC] is
+ repeated here, but it is suggested that the reader refer to those
+ documents for the exact procedures. 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
+ messages can be forwarded to any environment without modification.
+
+
+
+Schaad, et al. Standards Track [Page 22]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ 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 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 header fields
+ (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 header
+ fields. It is up to the receiving client to decide how to present
+ this "inner" header along with the unprotected "outer" header. Given
+ the security difference between headers, it is RECOMMENDED that the
+ receiving client provide a distinction between header fields,
+ depending on where they are located.
+
+ 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.
+
+3.1.1. 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 media type
+ and subtype of an entity and are not described here. Instead, the
+ standard for the particular media 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, that can be considered their canonical representation.
+
+
+
+Schaad, et al. Standards Track [Page 23]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ 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].
+
+ 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 field is
+ present, the transfer encoding is presumed to be 7BIT.
+
+ As a rule, S/MIME implementations SHOULD use transfer encoding as
+ 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 is 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 end 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.
+
+ In the case where S/MIME implementations can determine that all
+ intended recipients are capable of handling inner (all but the
+ outermost) binary MIME objects, implementations 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)
+ unnecessarily expands the message size. Implementations MAY
+ determine that recipient implementations are capable of
+ handling inner binary MIME entities by (1) interpreting the
+ id-cap-preferBinaryInside SMIMECapabilities attribute, (2) prior
+ agreement, or (3) other means.
+
+
+
+
+Schaad, et al. Standards Track [Page 24]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ 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 as
+ described in Section 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 already
+ 7-bit data need no transfer encoding. Entities such as 8-bit text
+ and binary data can be encoded with quoted-printable or base64
+ 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 cannot 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.
+
+ [RFC1847] prohibits an agent from changing the transfer encoding of
+ the first part of a multipart/signed message. If a compliant agent
+ that cannot transmit 8-bit or binary data encountered 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 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
+ the transfer-encoded parts all MUST be <CR><LF>.
+
+
+
+
+Schaad, et al. Standards Track [Page 25]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ Note that this example is not an example 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--
+
+3.2. The application/pkcs7-mime Media Type
+
+ The application/pkcs7-mime media type is used to carry CMS content
+ types, including EnvelopedData, SignedData, and CompressedData. The
+ details of constructing these entities are described in subsequent
+ sections. This section describes the general characteristics of the
+ application/pkcs7-mime media type.
+
+ The carried CMS object always contains a MIME entity that is prepared
+ as described in Section 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 base64
+ transfer encoding is appropriate -- in particular, when used with
+ SMTP transport. The transfer encoding used depends on the transport
+
+
+
+Schaad, et al. Standards Track [Page 26]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ through which the object is to be sent and is not a characteristic of
+ the media 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 in Section 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 Content-Type header
+ field 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 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 [RFC2183] with the "filename" parameter.
+ If a sending agent emits the above parameters, the value of the
+ parameters SHOULD be a filename with the appropriate extension:
+
+ File
+ Media Type Extension
+ -------------------------------------------------------------------
+ application/pkcs7-mime (SignedData, EnvelopedData, .p7m
+ AuthEnvelopedData)
+ application/pkcs7-mime (degenerate SignedData certificate .p7c
+ management message)
+ application/pkcs7-mime (CompressedData) .p7z
+ application/pkcs7-signature (SignedData) .p7s
+
+ In addition, the filename 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 filename 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 media type
+ to application/octet-stream and treat it as a generic attachment,
+ thus losing the type information. However, the suggested filename
+
+
+
+Schaad, et al. Standards Track [Page 27]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ 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 standalone 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 media 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.
+
+ Name CMS Type Inner Content
+ ----------------------------------------------------------
+ enveloped-data EnvelopedData id-data
+ signed-data SignedData id-data
+ certs-only SignedData id-data
+ compressed-data CompressedData id-data
+ authEnveloped-data AuthEnvelopedData 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 three values for smime-type SHOULD be assigned: "signed-*",
+ "authEnv-*", and "enveloped-*". 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.2.16.840.1.101.3.4.1.2" would be AES-128 CBC).
+
+ It is explicitly intended that this field be a suitable hint for mail
+ client applications to indicate whether a message is "signed",
+ "authEnveloped", or "enveloped" without having to tunnel into the CMS
+ payload.
+
+
+
+
+
+Schaad, et al. Standards Track [Page 28]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ A registry for additional smime-type parameter values has been
+ defined in [RFC7114].
+
+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. The
+ "enveloped-only" structure does not support authenticated symmetric
+ algorithms. Use the "authenticated enveloped" structure for these
+ algorithms. Thus, 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 to
+ Section 3.1.
+
+ Step 2. The MIME entity and other required data are processed into a
+ CMS object of type EnvelopedData. In addition to encrypting
+ a copy of the content-encryption key (CEK) for each
+ recipient, a copy of the CEK SHOULD be encrypted for the
+ originator and included in the EnvelopedData (see [RFC5652],
+ Section 6).
+
+ 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; name=smime.p7m;
+ smime-type=enveloped-data
+ Content-Transfer-Encoding: base64
+ Content-Disposition: attachment; filename=smime.p7m
+
+ MIIBHgYJKoZIhvcNAQcDoIIBDzCCAQsCAQAxgcAwgb0CAQAwJjASMRAwDgYDVQQDEw
+ dDYXJsUlNBAhBGNGvHgABWvBHTbi7NXXHQMA0GCSqGSIb3DQEBAQUABIGAC3EN5nGI
+ iJi2lsGPcP2iJ97a4e8kbKQz36zg6Z2i0yx6zYC4mZ7mX7FBs3IWg+f6KgCLx3M1eC
+ bWx8+MDFbbpXadCDgO8/nUkUNYeNxJtuzubGgzoyEd8Ch4H/dd9gdzTd+taTEgS0ip
+ dSJuNnkVY4/M652jKKHRLFf02hosdR8wQwYJKoZIhvcNAQcBMBQGCCqGSIb3DQMHBA
+ gtaMXpRwZRNYAgDsiSf8Z9P43LrY4OxUk660cu1lXeCSFOSOpOJ7FuVyU=
+
+
+
+
+Schaad, et al. Standards Track [Page 29]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+3.4. Creating an Authenticated Enveloped-Only Message
+
+ This section describes the format for enveloping a MIME entity
+ without signing it. Authenticated enveloped messages provide
+ confidentiality and data integrity. It is important to note that
+ sending authenticated enveloped messages does not provide for proof
+ of origination when using S/MIME. It is possible for a third party
+ to replace ciphertext in such a way that the processed message will
+ still be valid, but the meaning can be altered. However, this is
+ substantially more difficult than it is for an enveloped-only
+ message, as the algorithm does provide a level of authentication.
+ Any recipient for whom the message is encrypted can replace it
+ without detection.
+
+ Step 1. The MIME entity to be enveloped is prepared according to
+ Section 3.1.
+
+ Step 2. The MIME entity and other required data are processed into a
+ CMS object of type AuthEnvelopedData. In addition to
+ encrypting a copy of the CEK for each recipient, a copy of
+ the CEK SHOULD be encrypted for the originator and included
+ in the AuthEnvelopedData (see [RFC5083]).
+
+ Step 3. The AuthEnvelopedData 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 authenticated enveloped-only messages is
+ "authEnveloped-data". The file extension for this type of message
+ is ".p7m".
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+Schaad, et al. Standards Track [Page 30]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ A sample message would be:
+
+ Content-Type: application/pkcs7-mime; smime-type=authEnveloped-data;
+ name=smime.p7m
+ Content-Transfer-Encoding: base64
+ Content-Disposition: attachment; filename=smime.p7m
+
+ MIIDWQYLKoZIhvcNAQkQARegggNIMIIDRAIBADGBvjCBuwIBADAmMBIxEDAO
+ BgNVBAMTB0NhcmxSU0ECEEY0a8eAAFa8EdNuLs1dcdAwCwYJKoZIhvcNAQEB
+ BIGAgyZJo0ERTxA4xdTri5P5tVMyh0RARepTUCORZvlUbcUlaI8IpJZH3/J1
+ Fv6MxTRS4O/K+ZcTlQmYeWLQvwdltQdOIP3mhpqXzTnOYhTK1IDtF2zx75Lg
+ vE+ilpcLIzXfJB4RCBPtBWaHAof4Wb+VMQvLkk9OolX4mRSH1LPktgAwggJq
+ BgkqhkiG9w0BBwEwGwYJYIZIAWUDBAEGMA4EDGPizioC9OHSsnNx4oCCAj7Y
+ Cb8rOy8+55106newEJohC/aDgWbJhrMKzSOwa7JraXOV3HXD3NvKbl665dRx
+ vmDwSCNaLCRU5q8/AxQx2SvnAbM+JKcEfC/VFdd4SiHNiUECAApLku2rMi5B
+ WrhW/FXmx9d+cjum2BRwB3wj0q1wajdB0/kVRbQwg697dnlYyUog4vpJERjr
+ 7KAkawZx1RMHaM18wgZjUNpCBXFS3chQi9mTBp2i2Hf5iZ8OOtTx+rCQUmI6
+ Jhy03vdcPCCARBjn3v0d3upZYDZddMA41CB9fKnnWFjadV1KpYwv80tqsEfx
+ Vo0lJQ5VtJ8MHJiBpLVKadRIZ4iH2ULC0JtN5mXE1SrFKh7cqbJ4+7nqSRL3
+ oBTud3rX41DGshOjpqcYHT4sqYlgZkc6dp0g1+hF1p3cGmjHdpysV2NVSUev
+ ghHbvSqhIsXFzRSWKiZOigmlkv3R5LnjpYyP4brM62Jl7y0qborvV4dNMz7m
+ D+5YxSlH0KAe8z6TT3LHuQdN7QCkFoiUSCaNhpAFaakkGIpqcqLhpOK4lXxt
+ kptCG93eUwNCcTxtx6bXufPR5TUHohvZvfeqMp42kL37FJC/A8ZHoOxXy8+X
+ X5QYxCQNuofWlvnIWv0Nr8w65x6lgVjPYmd/cHwzQKBTBMXN6pBud/PZL5zF
+ tw3QHlQkBR+UflMWZKeN9L0KdQ27mQlCo5gQS85aifxoiiA2v9+0hxZw91rP
+ IW4D+GS7oMMoKj8ZNyCJJsyf5smRZ+WxeBoolb3+TiGcBBCsRnfe6noLZiFO
+ 6Zeu2ZwE
+
+3.5. Creating a Signed-Only Message
+
+ There are two formats for signed messages defined for S/MIME:
+
+ - application/pkcs7-mime with SignedData.
+
+ - multipart/signed.
+
+ In general, the multipart/signed form is preferred for sending, and
+ receiving agents MUST be able to handle both.
+
+
+
+
+
+
+
+
+
+
+
+
+
+Schaad, et al. Standards Track [Page 31]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+3.5.1. Choosing a Format for Signed-Only Messages
+
+ There are no hard-and-fast rules as to when a particular signed-only
+ format is chosen. 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 or not they have S/MIME software.
+ 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.
+
+ 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 that would break the signature.
+
+3.5.2. Signing Using application/pkcs7-mime with SignedData
+
+ This signing format uses the application/pkcs7-mime media type. The
+ steps to create this format are as follows:
+
+ Step 1. The MIME entity is prepared according to Section 3.1.
+
+ Step 2. The MIME entity and other required data are 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".
+
+
+
+
+
+
+
+
+
+
+Schaad, et al. Standards Track [Page 32]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ 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
+
+ MIIDmQYJKoZIhvcNAQcCoIIDijCCA4YCAQExCTAHBgUrDgMCGjAtBgkqhkiG9w0BBw
+ GgIAQeDQpUaGlzIGlzIHNvbWUgc2FtcGxlIGNvbnRlbnQuoIIC4DCCAtwwggKboAMC
+ AQICAgDIMAkGByqGSM44BAMwEjEQMA4GA1UEAxMHQ2FybERTUzAeFw05OTA4MTcwMT
+ EwNDlaFw0zOTEyMzEyMzU5NTlaMBMxETAPBgNVBAMTCEFsaWNlRFNTMIIBtjCCASsG
+ ByqGSM44BAEwggEeAoGBAIGNze2D6gqeOT7CSCij5EeT3Q7XqA7sU8WrhAhP/5Thc0
+ h+DNbzREjR/p+vpKGJL+HZMMg23j+bv7dM3F9piuR10DcMkQiVm96nXvn89J8v3UOo
+ i1TxP7AHCEdNXYjDw7Wz41UIddU5dhDEeL3/nbCElzfy5FEbteQJllzzflvbAhUA4k
+ emGkVmuBPG2o+4NyErYov3k80CgYAmONAUiTKqOfs+bdlLWWpMdiM5BAI1XPLLGjDD
+ HlBd3ZtZ4s2qBT1YwHuiNrhuB699ikIlp/R1z0oIXks+kPht6pzJIYo7dhTpzi5dow
+ fNI4W4LzABfG1JiRGJNkS9+MiVSlNWteL5c+waYTYfEX/Cve3RUP+YdMLRgUpgObo2
+ OQOBhAACgYBc47ladRSWC6l63eM/qeysXty9txMRNKYWiSgRI9k0hmd1dRMSPUNbb+
+ VRv/qJ8qIbPiR9PQeNW2PIu0WloErjhdbOBoA/6CN+GvIkq1MauCcNHu8Iv2YUgFxi
+ rGX6FYvxuzTU0pY39mFHssQyhPB+QUD9RqdjTjPypeL08oPluKOBgTB/MAwGA1UdEw
+ EB/wQCMAAwDgYDVR0PAQH/BAQDAgbAMB8GA1UdIwQYMBaAFHBEPoIub4feStN14z0g
+ vEMrk/EfMB0GA1UdDgQWBBS+bKGz48H37UNwpM4TAeL945f+zTAfBgNVHREEGDAWgR
+ RBbGljZURTU0BleGFtcGxlLmNvbTAJBgcqhkjOOAQDAzAAMC0CFFUMpBkfQiuJcSIz
+ jYNqtT1na79FAhUAn2FTUlQLXLLd2ud2HeIQUltDXr0xYzBhAgEBMBgwEjEQMA4GA1
+ UEAxMHQ2FybERTUwICAMgwBwYFKw4DAhowCQYHKoZIzjgEAwQuMCwCFD1cSW6LIUFz
+ eXle3YI5SKSBer/sAhQmCq7s/CTFHOEjgASeUjbMpx5g6A==
+
+3.5.3. 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 media type described in [RFC1847]. The
+ multipart/signed media 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.
+
+3.5.3.1. The application/pkcs7-signature Media Type
+
+ This media 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".
+
+
+
+
+
+Schaad, et al. Standards Track [Page 33]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+3.5.3.2. Creating a multipart/signed Message
+
+ Step 1. The MIME entity to be signed is prepared according to
+ Section 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 in Section 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.
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+Schaad, et al. Standards Track [Page 34]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ 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 [RFC1847].
+ The values to be placed in the micalg parameter SHOULD be from the
+ following:
+
+ Algorithm Value Used
+ -----------------------------------------------------------
+ MD5* md5
+ SHA-1* sha-1
+ SHA-224 sha-224
+ SHA-256 sha-256
+ SHA-384 sha-384
+ SHA-512 sha-512
+ Any other (defined separately in the algorithm profile
+ or "unknown" if not defined)
+
+ *Note: MD5 and SHA-1 are historical and no longer considered secure.
+ See Appendix B for details.
+
+ (Historical note: Some early implementations of S/MIME emitted and
+ expected "rsa-md5", "rsa-sha1", and "sha1" for the micalg parameter.)
+ Receiving agents SHOULD be able to recover gracefully from a micalg
+ parameter value that they do not recognize. Future values for this
+ parameter will be taken from the IANA "Hash Function Textual Names"
+ registry.
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+Schaad, et al. Standards Track [Page 35]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+3.5.3.3. Sample multipart/signed Message
+
+ Content-Type: multipart/signed;
+ micalg=sha-256;
+ boundary="----=_NextBoundary____Fri,_06_Sep_2002_00:25:21";
+ protocol="application/pkcs7-signature"
+
+ This is a multipart message in MIME format.
+
+ ------=_NextBoundary____Fri,_06_Sep_2002_00:25:21
+
+ This is some sample content.
+ ------=_NextBoundary____Fri,_06_Sep_2002_00:25:21
+ Content-Type: application/pkcs7-signature; name=smime.p7s
+ Content-Transfer-Encoding: base64
+ Content-Disposition: attachment; filename=smime.p7s
+
+ MIIBJgYJKoZIhvcNAQcCoIIBFzCCARMCAQExADALBgkqhkiG9w0BBwExgf4w
+ gfsCAQIwJjASMRAwDgYDVQQDEwdDYXJsUlNBAhBGNGvHgABWvBHTbi7EELOw
+ MAsGCWCGSAFlAwQCAaAxMC8GCSqGSIb3DQEJBDEiBCCxwpZGNZzTSsugsn+f
+ lEidzQK4mf/ozKqfmbxhcIkKqjALBgkqhkiG9w0BAQsEgYB0XJV7fjPa5Nuh
+ oth5msDfP8A5urYUMjhNpWgXG8ae3XpppqVrPi2nVO41onHnkByjkeD/wc31
+ A9WH8MzFQgSTsrJ65JvffTTXkOpRPxsSHn3wJFwP/atWHkh8YK/jR9bULhUl
+ Mv5jQEDiwVX5DRasxu6Ld8zv9u5/TsdBNiufGw==
+
+ ------=_NextBoundary____Fri,_06_Sep_2002_00:25:21--
+
+ The content that is digested (the first part of the multipart/signed)
+ consists of the bytes:
+
+ 54 68 69 73 20 69 73 20 73 6f 6d 65 20 73 61 6d 70 6c 65 20 63 6f 6e
+ 74 65 6e 74 2e 0d 0a
+
+3.6. Creating a Compressed-Only Message
+
+ This section describes the format for compressing a MIME entity.
+ Please note that versions of S/MIME prior to version 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 [RFC3274] and is the preferred method for compatibility.
+
+ Step 1. The MIME entity to be compressed is prepared according to
+ Section 3.1.
+
+ Step 2. The MIME entity and other required data are processed into a
+ CMS object of type CompressedData.
+
+
+
+
+
+Schaad, et al. Standards Track [Page 36]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ 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
+
+ eNoLycgsVgCi4vzcVIXixNyCnFSF5Py8ktS8Ej0AlCkKVA==
+
+3.7. Multiple Operations
+
+ The signed-only, enveloped-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 where automatic signature verification is desired, as no
+ private key material is required to verify a signature.
+
+ There are security ramifications related 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 and 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.
+
+
+
+
+
+Schaad, et al. Standards Track [Page 37]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ When using compression, keep the following guidelines in mind:
+
+ - Compression of encrypted data that is transferred as binary data
+ is discouraged, since it will not yield significant compression.
+ Encrypted data that is transferred as base64-encoded data could
+ benefit as well.
+
+ - If a lossy compression algorithm is used with signing, you will
+ need to compress first, then sign.
+
+3.8. Creating a Certificate Management Message
+
+ The certificate management message or MIME entity is used to
+ transport certificates and/or Certificate Revocation Lists (CRLs),
+ such as in response to a registration request.
+
+ Step 1. The certificates and/or CRLs are made available to the CMS
+ generating process that creates a CMS object of type
+ SignedData. The SignedData encapContentInfo eContent field
+ MUST be absent, and the signerInfos field MUST be empty.
+
+ 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".
+
+3.9. 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 certification 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 v4.0 does not
+ require a particular certificate request mechanism.
+
+
+
+
+
+
+
+
+Schaad, et al. Standards Track [Page 38]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+3.10. 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 field or the "filename" parameter in the
+ Content-Disposition header field. The MIME parameters that carry the
+ file suffix are not listed below.
+
+ Media Type Parameters File Suffix
+ ---------------------------------------------------------------------
+ application/pkcs7-mime N/A N/A
+
+ multipart/signed protocol= N/A
+ "application/pkcs7-signature"
+
+ application/octet-stream N/A p7m, p7s,
+ p7c, p7z
+
+4. 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
+ [RFC5750].
+
+ 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 as
+ to guarantee their later retrieval.
+
+
+
+
+
+
+
+
+
+
+
+
+Schaad, et al. Standards Track [Page 39]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+4.1. Key Pair Generation
+
+ All key pairs MUST be generated from a good source of
+ non-deterministic random input [RFC4086], and the private key MUST be
+ protected in a secure fashion.
+
+ An S/MIME user agent MUST NOT generate asymmetric keys less than
+ 2048 bits for use with an RSA signature algorithm.
+
+ For 2048-bit through 4096-bit RSA with SHA-256, see [RFC5754] and
+ [FIPS186-4]. The first reference provides the signature algorithm's
+ OID, and the second provides the signature algorithm's definition.
+
+ For RSASSA-PSS with SHA-256, see [RFC4056]. For RSAES-OAEP, see
+ [RFC3560].
+
+4.2. Signature Generation
+
+ The following are the requirements for an S/MIME agent when
+ generating RSA and RSASSA-PSS signatures:
+
+ key size <= 2047 : SHOULD NOT (Note 2)
+ 2048 <= key size <= 4096 : SHOULD (Note 1)
+ 4096 < key size : MAY (Note 1)
+
+ Note 1: See Security Considerations in Section 6.
+ Note 2: See Historical Mail Considerations in Appendix B.
+
+ Key sizes for ECDSA and EdDSA are fixed by the curve.
+
+4.3. Signature Verification
+
+ The following are the requirements for S/MIME receiving agents during
+ verification of RSA and RSASSA-PSS signatures:
+
+ key size <= 2047 : SHOULD NOT (Note 2)
+ 2048 <= key size <= 4096 : MUST (Note 1)
+ 4096 < key size : MAY (Note 1)
+
+ Note 1: See Security Considerations in Section 6.
+ Note 2: See Historical Mail Considerations in Appendix B.
+
+ Key sizes for ECDSA and EdDSA are fixed by the curve.
+
+
+
+
+
+
+
+
+Schaad, et al. Standards Track [Page 40]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+4.4. Encryption
+
+ The following are the requirements for an S/MIME agent when
+ establishing keys for content encryption using the RSA and RSA-OAEP
+ algorithms:
+
+ key size <= 2047 : SHOULD NOT (Note 2)
+ 2048 <= key size <= 4096 : SHOULD (Note 1)
+ 4096 < key size : MAY (Note 1)
+
+ Note 1: See Security Considerations in Section 6.
+ Note 2: See Historical Mail Considerations in Appendix B.
+
+ Key sizes for ECDH are fixed by the curve.
+
+4.5. Decryption
+
+ The following are the requirements for an S/MIME agent when
+ establishing keys for content decryption using the RSA and RSAES-OAEP
+ algorithms:
+
+ key size <= 2047 : MAY (Note 2)
+ 2048 <= key size <= 4096 : MUST (Note 1)
+ 4096 < key size : MAY (Note 1)
+
+ Note 1: See Security Considerations in Section 6.
+ Note 2: See Historical Mail Considerations in Appendix B.
+
+ Key sizes for ECDH are fixed by the curve.
+
+5. IANA Considerations
+
+ This section (1) updates the media type registrations for
+ application/pkcs7-mime and application/pkcs7-signature to refer to
+ this document as opposed to RFC 5751, (2) adds authEnveloped-data to
+ the list of values for smime-type, and (3) updates references from
+ RFC 5751 to this document in general.
+
+ Note that other documents can define additional media types for
+ S/MIME.
+
+
+
+
+
+
+
+
+
+
+
+Schaad, et al. Standards Track [Page 41]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+5.1. Media Type for application/pkcs7-mime
+
+ Type name: application
+
+ Subtype Name: pkcs7-mime
+
+ Required Parameters: NONE
+
+ Optional Parameters: smime-type
+ name
+
+ Encoding Considerations: See Section 3 of this document
+
+ Security Considerations: See Section 6 of this document
+
+ Interoperability Considerations: See Sections 1-6 of this document
+
+ Published Specification: RFC 2311, RFC 2633, RFC 5751,
+ and this document
+
+ Applications that use this media type: Security applications
+
+ Fragment identifier considerations: N/A
+
+ Additional information:
+ Deprecated alias names for this type: N/A
+ Magic number(s): N/A
+ File extensions(s): See Section 3.2.1 of this document
+ Macintosh file type code(s): N/A
+
+ Person & email address to contact for further information:
+ The IESG <iesg@ietf.org>
+
+ Intended usage: COMMON
+
+ Restrictions on usage: NONE
+
+ Author: Sean Turner
+
+ Change Controller: LAMPS working group delegated from the IESG
+
+
+
+
+
+
+
+
+
+
+
+Schaad, et al. Standards Track [Page 42]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+5.2. Media Type for application/pkcs7-signature
+
+ Type name: application
+
+ Subtype Name: pkcs7-signature
+
+ Required Parameters: N/A
+
+ Optional Parameters: N/A
+
+ Encoding Considerations: See Section 3 of this document
+
+ Security Considerations: See Section 6 of this document
+
+ Interoperability Considerations: See Sections 1-6 of this document
+
+ Published Specification: RFC 2311, RFC 2633, RFC 5751,
+ and this document
+
+ Applications that use this media type: Security applications
+
+ Fragment identifier considerations: N/A
+
+ Additional information:
+ Deprecated alias names for this type: N/A
+ Magic number(s): N/A
+ File extensions(s): See Section 3.2.1 of this document
+ Macintosh file type code(s): N/A
+
+ Person & email address to contact for further information:
+ The IESG <iesg@ietf.org>
+
+ Intended usage: COMMON
+
+ Restrictions on usage: N/A
+
+ Author: Sean Turner
+
+ Change Controller: LAMPS working group delegated from the IESG
+
+
+
+
+
+
+
+
+
+
+
+
+Schaad, et al. Standards Track [Page 43]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+5.3. authEnveloped-data smime-type
+
+ IANA has registered the following value in the "Parameter Values for
+ the smime-type Parameter" registry.
+
+ smime-type value: authEnveloped-data
+
+ Reference: RFC 8551, Section 3.2.2
+
+5.4. Reference Updates
+
+ IANA is to update all references to RFC 5751 to this document. Known
+ registries to be updated are "CoAP Content-Formats" and "media-
+ types".
+
+6. Security Considerations
+
+ Cryptographic algorithms will be broken or weakened over time.
+ Implementers and users need to check that the cryptographic
+ algorithms listed in this document continue to provide the expected
+ level of security. The IETF from time to time may issue documents
+ dealing with the current state of the art. For example:
+
+ - The Million Message Attack described in RFC 3218 [RFC3218].
+
+ - The Diffie-Hellman "small-subgroup" attacks described in RFC 2785
+ [RFC2785].
+
+ - The attacks against hash algorithms described in RFC 4270
+ [RFC4270].
+
+ This specification uses Public-Key Cryptography technologies. It is
+ assumed that the private key is protected to ensure that it is not
+ accessed or altered by unauthorized parties.
+
+ It is impossible for most people or software to estimate the value of
+ a message's content. Further, it is impossible for most people or
+ software to estimate the actual cost of recovering an encrypted
+ message's content 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 process a message's content. Thus,
+ choosing between different key sizes (or choosing whether to just use
+ plaintext) is also impossible for most people or software. 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.
+
+
+
+
+
+Schaad, et al. Standards Track [Page 44]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ The choice of 2048 bits as an RSA asymmetric key size in this
+ specification is based on the desire to provide at least 100 bits of
+ security. The key sizes that must be supported to conform to this
+ specification seem appropriate for the Internet, based on [RFC3766].
+ Of course, there are environments, such as financial and medical
+ systems, that may select different key sizes. For this reason, an
+ implementation MAY support key sizes beyond those recommended in this
+ specification.
+
+ Receiving agents that validate signatures and sending agents that
+ encrypt messages need to be cautious of cryptographic processing
+ usage when validating signatures and encrypting messages using keys
+ larger than those mandated in this specification. An attacker could
+ send certificates with keys that would result in excessive
+ cryptographic processing -- for example, keys larger than those
+ mandated in this specification, as such keys could swamp the
+ processing element. Agents that use such keys without first
+ validating the certificate to a trust anchor are advised to have some
+ sort of cryptographic resource management system to prevent such
+ attacks.
+
+ Some cryptographic algorithms such as RC2 offer little actual
+ security over sending plaintext. Other algorithms such as TripleDES
+ provide security but are no longer considered to be state of the art.
+ S/MIME requires the use of current state-of-the-art algorithms such
+ as AES and provides the ability to announce cryptographic
+ capabilities to parties with whom you communicate. This allows the
+ sender to create messages that can use the strongest common
+ encryption algorithm. Using algorithms such as RC2 is never
+ recommended unless the only alternative is no cryptography.
+
+ RSA and DSA keys of less than 2048 bits are now considered by many
+ experts to be cryptographically insecure (due to advances in
+ computing power) and should no longer be used to protect messages.
+ Such keys were previously considered secure, so processing previously
+ received signed and encrypted mail will often result in the use of
+ weak keys. Implementations that wish to support previous versions of
+ S/MIME or process old messages need to consider the security risks
+ that result from smaller key sizes (e.g., spoofed messages) versus
+ the costs of denial of service. If an implementation supports
+ verification of digital signatures generated with RSA and DSA keys of
+ less than 1024 bits, it MUST warn the user. Implementers should
+ consider providing different warnings for newly received messages and
+ previously stored messages. Server implementations (e.g., secure
+ mail list servers) where user warnings are not appropriate SHOULD
+ reject messages with weak signatures.
+
+
+
+
+
+Schaad, et al. Standards Track [Page 45]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ 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 digital signatures.
+
+ 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 in EnvelopedData 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. This is one of the reasons for moving from
+ EnvelopedData to AuthEnvelopedData, as the authenticated encryption
+ algorithms provide the authentication without needing the SignedData
+ layer.
+
+ If an implementation is concerned about compliance with National
+ Institute of Standards and Technology (NIST) key size
+ recommendations, then see [SP800-57].
+
+ If messaging environments make use of the fact that a message is
+ signed to change the behavior of message processing (examples would
+ be running rules or UI display hints), without first verifying that
+ the message is actually signed and knowing the state of the
+ signature, this can lead to incorrect handling of the message.
+ Visual indicators on messages may need to have the signature
+ validation code checked periodically if the indicator is supposed to
+ give information on the current status of a message.
+
+ Many people assume that the use of an authenticated encryption
+ algorithm is all that is needed for the sender of the message to be
+ authenticated. In almost all cases, this is not a correct statement.
+ There are a number of preconditions that need to hold for an
+ authenticated encryption algorithm to provide this service:
+
+ - The starting key must be bound to a single entity. The use of a
+ group key only would allow for the statement that a message was
+ sent by one of the entities that held the key but will not
+ identify a specific entity.
+
+
+
+
+
+
+
+Schaad, et al. Standards Track [Page 46]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ - The message must have exactly one sender and one recipient.
+ Having more than one recipient would allow for the second
+ recipient to create a message that the first recipient would
+ believe is from the sender by stripping the second recipient from
+ the message.
+
+ - A direct path needs to exist from the starting key to the key used
+ as the CEK. That path needs to guarantee that no third party
+ could have seen the resulting CEK. This means that one needs to
+ be using an algorithm that is called a "Direct Encryption" or a
+ "Direct Key Agreement" algorithm in other contexts. This means
+ that the starting key is (1) used directly as the CEK or (2) used
+ to create a secret that is then transformed into the CEK via a
+ KDF step.
+
+ S/MIME implementations almost universally use ephemeral-static rather
+ than static-static key agreement and do not use a shared secret for
+ encryption. This means that the first precondition is not met.
+ [RFC6278] defines how to use static-static key agreement with CMS, so
+ the first precondition can be met. Currently, all S/MIME key
+ agreement methods derive a key-encryption key (KEK) and wrap a CEK.
+ This violates the third precondition above. New key agreement
+ algorithms that directly created the CEK without creating an
+ intervening KEK would need to be defined.
+
+ Even when all of the preconditions are met and origination of a
+ message is established by the use of an authenticated encryption
+ algorithm, users need to be aware that there is no way to prove this
+ to a third party. This is because either of the parties can
+ successfully create the message (or just alter the content) based on
+ the fact that the CEK is going to be known to both parties. Thus,
+ the origination is always built on a presumption that "I did not send
+ this message to myself."
+
+ All of the authenticated encryption algorithms in this document use
+ counter mode for the encryption portion of the algorithm. This means
+ that the length of the plaintext will always be known, as the
+ ciphertext length and the plaintext length are always the same. This
+ information can enable passive observers to infer information based
+ solely on the length of the message. Applications for which this is
+ a concern need to provide some type of padding so that the length of
+ the message does not provide this information.
+
+ When compression is used with encryption, it has the potential to
+ provide an additional layer of security. However, care needs to be
+ taken when designing a protocol that relies on using compression, so
+ as not to create a compression oracle. Compression oracle attacks
+ require an adaptive input to the process and attack the unknown
+
+
+
+Schaad, et al. Standards Track [Page 47]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ content of a message based on the length of the compressed output.
+ This means that no attack on the encryption key is necessarily
+ required.
+
+ A recent paper on S/MIME and OpenPGP email security [Efail] has
+ pointed out a number of problems with the current S/MIME
+ specifications and how people have implemented mail clients. Due to
+ the nature of how CBC mode operates, the modes allow for malleability
+ of plaintexts. This malleability allows for attackers to make
+ changes in the ciphertext and, if parts of the plaintext are known,
+ create arbitrary blocks of plaintext. These changes can be made
+ without the weak integrity check in CBC mode being triggered. This
+ type of attack can be prevented by the use of an Authenticated
+ Encryption with Associated Data (AEAD) algorithm with a more robust
+ integrity check on the decryption process. It is therefore
+ recommended that mail systems migrate to using AES-GCM as quickly as
+ possible and that the decrypted content not be acted on prior to
+ finishing the integrity check.
+
+ The other attack that is highlighted in [Efail] is due to an error in
+ how mail clients deal with HTML and multipart/mixed messages.
+ Clients MUST require that a text/html content type be a complete HTML
+ document (per [RFC1866]). Clients SHOULD treat each of the different
+ pieces of the multipart/mixed construct as being of different
+ origins. Clients MUST treat each encrypted or signed piece of a MIME
+ message as being of different origins both from unprotected content
+ and from each other.
+
+7. References
+
+7.1. Reference Conventions
+
+ [ASN.1] refers to [X.680], [X.681], [X.682], and [X.683].
+
+ [CMS] refers to [RFC5083] and [RFC5652].
+
+ [ESS] refers to [RFC2634] and [RFC5035].
+
+ [MIME-SPEC] refers to [RFC2045], [RFC2046], [RFC2047], [RFC2049],
+ [RFC6838], and [RFC4289].
+
+ [SMIMEv2] refers to [RFC2311], [RFC2312], [RFC2313], [RFC2314], and
+ [RFC2315].
+
+ [SMIMEv3] refers to [RFC2630], [RFC2631], [RFC2632], [RFC2633],
+ [RFC2634], and [RFC5035].
+
+
+
+
+
+Schaad, et al. Standards Track [Page 48]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ [SMIMEv3.1] refers to [RFC2634], [RFC5035], [RFC5652], [RFC5750], and
+ [RFC5751].
+
+ [SMIMEv3.2] refers to [RFC2634], [RFC3850], [RFC3851], [RFC3852], and
+ [RFC5035].
+
+ [SMIMEv4] refers to [RFC2634], [RFC5035], [RFC5652], [RFC8550], and
+ this document.
+
+7.2. Normative References
+
+ [CHARSETS] IANA, "Character sets assigned by IANA",
+ <http://www.iana.org/assignments/character-sets>.
+
+ [FIPS186-4]
+ National Institute of Standards and Technology (NIST),
+ "Digital Signature Standard (DSS)", Federal Information
+ Processing Standards Publication 186-4,
+ DOI 10.6028/NIST.FIPS.186-4, July 2013,
+ <https://nvlpubs.nist.gov/nistpubs/fips/
+ nist.fips.186-4.pdf>.
+
+ [RFC1847] Galvin, J., Murphy, S., Crocker, S., and N. Freed,
+ "Security Multiparts for MIME: Multipart/Signed and
+ Multipart/Encrypted", RFC 1847, DOI 10.17487/RFC1847,
+ October 1995, <https://www.rfc-editor.org/info/rfc1847>.
+
+ [RFC2045] Freed, N. and N. Borenstein, "Multipurpose Internet Mail
+ Extensions (MIME) Part One: Format of Internet Message
+ Bodies", RFC 2045, DOI 10.17487/RFC2045, November 1996,
+ <https://www.rfc-editor.org/info/rfc2045>.
+
+ [RFC2046] Freed, N. and N. Borenstein, "Multipurpose Internet Mail
+ Extensions (MIME) Part Two: Media Types", RFC 2046,
+ DOI 10.17487/RFC2046, November 1996,
+ <https://www.rfc-editor.org/info/rfc2046>.
+
+ [RFC2047] Moore, K., "MIME (Multipurpose Internet Mail Extensions)
+ Part Three: Message Header Extensions for Non-ASCII Text",
+ RFC 2047, DOI 10.17487/RFC2047, November 1996,
+ <https://www.rfc-editor.org/info/rfc2047>.
+
+ [RFC2049] Freed, N. and N. Borenstein, "Multipurpose Internet Mail
+ Extensions (MIME) Part Five: Conformance Criteria and
+ Examples", RFC 2049, DOI 10.17487/RFC2049, November 1996,
+ <https://www.rfc-editor.org/info/rfc2049>.
+
+
+
+
+
+Schaad, et al. Standards Track [Page 49]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ [RFC2119] Bradner, S., "Key words for use in RFCs to Indicate
+ Requirement Levels", BCP 14, RFC 2119,
+ DOI 10.17487/RFC2119, March 1997,
+ <https://www.rfc-editor.org/info/rfc2119>.
+
+ [RFC2183] Troost, R., Dorner, S., and K. Moore, Ed., "Communicating
+ Presentation Information in Internet Messages: The
+ Content-Disposition Header Field", RFC 2183,
+ DOI 10.17487/RFC2183, August 1997,
+ <https://www.rfc-editor.org/info/rfc2183>.
+
+ [RFC2634] Hoffman, P., Ed., "Enhanced Security Services for S/MIME",
+ RFC 2634, DOI 10.17487/RFC2634, June 1999,
+ <https://www.rfc-editor.org/info/rfc2634>.
+
+ [RFC3274] Gutmann, P., "Compressed Data Content Type for
+ Cryptographic Message Syntax (CMS)", RFC 3274,
+ DOI 10.17487/RFC3274, June 2002,
+ <https://www.rfc-editor.org/info/rfc3274>.
+
+ [RFC3370] Housley, R., "Cryptographic Message Syntax (CMS)
+ Algorithms", RFC 3370, DOI 10.17487/RFC3370, August 2002,
+ <https://www.rfc-editor.org/info/rfc3370>.
+
+ [RFC3560] Housley, R., "Use of the RSAES-OAEP Key Transport
+ Algorithm in Cryptographic Message Syntax (CMS)",
+ RFC 3560, DOI 10.17487/RFC3560, July 2003,
+ <https://www.rfc-editor.org/info/rfc3560>.
+
+ [RFC3565] Schaad, J., "Use of the Advanced Encryption Standard (AES)
+ Encryption Algorithm in Cryptographic Message Syntax
+ (CMS)", RFC 3565, DOI 10.17487/RFC3565, July 2003,
+ <https://www.rfc-editor.org/info/rfc3565>.
+
+ [RFC4289] Freed, N. and J. Klensin, "Multipurpose Internet Mail
+ Extensions (MIME) Part Four: Registration Procedures",
+ BCP 13, RFC 4289, DOI 10.17487/RFC4289, December 2005,
+ <https://www.rfc-editor.org/info/rfc4289>.
+
+ [RFC4056] Schaad, J., "Use of the RSASSA-PSS Signature Algorithm in
+ Cryptographic Message Syntax (CMS)", RFC 4056,
+ DOI 10.17487/RFC4056, June 2005,
+ <https://www.rfc-editor.org/info/rfc4056>.
+
+ [RFC4086] Eastlake 3rd, D., Schiller, J., and S. Crocker,
+ "Randomness Requirements for Security", BCP 106, RFC 4086,
+ DOI 10.17487/RFC4086, June 2005,
+ <https://www.rfc-editor.org/info/rfc4086>.
+
+
+
+Schaad, et al. Standards Track [Page 50]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ [RFC5083] Housley, R., "Cryptographic Message Syntax (CMS)
+ Authenticated-Enveloped-Data Content Type", RFC 5083,
+ DOI 10.17487/RFC5083, November 2007,
+ <https://www.rfc-editor.org/info/rfc5083>.
+
+ [RFC5084] Housley, R., "Using AES-CCM and AES-GCM Authenticated
+ Encryption in the Cryptographic Message Syntax (CMS)",
+ RFC 5084, DOI 10.17487/RFC5084, November 2007,
+ <https://www.rfc-editor.org/info/rfc5084>.
+
+ [RFC5652] Housley, R., "Cryptographic Message Syntax (CMS)", STD 70,
+ RFC 5652, DOI 10.17487/RFC5652, September 2009,
+ <https://www.rfc-editor.org/info/rfc5652>.
+
+ [RFC5753] Turner, S. and D. Brown, "Use of Elliptic Curve
+ Cryptography (ECC) Algorithms in Cryptographic Message
+ Syntax (CMS)", RFC 5753, DOI 10.17487/RFC5753,
+ January 2010, <https://www.rfc-editor.org/info/rfc5753>.
+
+ [RFC5754] Turner, S., "Using SHA2 Algorithms with Cryptographic
+ Message Syntax", RFC 5754, DOI 10.17487/RFC5754,
+ January 2010, <https://www.rfc-editor.org/info/rfc5754>.
+
+ [RFC6838] Freed, N., Klensin, J., and T. Hansen, "Media Type
+ Specifications and Registration Procedures", BCP 13,
+ RFC 6838, DOI 10.17487/RFC6838, January 2013,
+ <https://www.rfc-editor.org/info/rfc6838>.
+
+ [RFC8174] Leiba, B., "Ambiguity of Uppercase vs Lowercase in RFC
+ 2119 Key Words", BCP 14, RFC 8174, DOI 10.17487/RFC8174,
+ May 2017, <https://www.rfc-editor.org/info/rfc8174>.
+
+ [RFC8418] Housley, R., "Use of the Elliptic Curve Diffie-Hellman Key
+ Agreement Algorithm with X25519 and X448 in the
+ Cryptographic Message Syntax (CMS)", RFC 8418,
+ DOI 10.17487/RFC8418, August 2018,
+ <https://www.rfc-editor.org/info/rfc8418>.
+
+ [RFC8419] Housley, R., "Use of Edwards-Curve Digital Signature
+ Algorithm (EdDSA) Signatures in the Cryptographic Message
+ Syntax (CMS)", RFC 8419, DOI 10.17487/RFC8419,
+ August 2018, <https://www.rfc-editor.org/info/rfc8419>.
+
+ [RFC8550] Schaad, J., Ramsdell, B., and S. Turner,
+ "Secure/Multipurpose Internet Mail Extensions (S/MIME)
+ Version 4.0 Certificate Handling", RFC 8550,
+ DOI 10.17487/RFC8550, April 2019,
+ <https://www.rfc-editor.org/info/rfc8550>.
+
+
+
+Schaad, et al. Standards Track [Page 51]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ [X.680] "Information Technology - Abstract Syntax Notation One
+ (ASN.1): Specification of basic notation", ITU-T
+ Recommendation X.680, ISO/IEC 8824-1:2015, August 2015,
+ <https://www.itu.int/rec/T-REC-X.680>.
+
+ [X.681] "Information Technology - Abstract Syntax Notation One
+ (ASN.1): Information object specification", ITU-T
+ Recommendation X.681, ISO/IEC 8824-2:2015, August 2015,
+ <https://www.itu.int/rec/T-REC-X.681>.
+
+ [X.682] "Information Technology - Abstract Syntax Notation One
+ (ASN.1): Constraint specification", ITU-T
+ Recommendation X.682, ISO/IEC 8824-3:2015, August 2015,
+ <https://www.itu.int/rec/T-REC-X.682>.
+
+ [X.683] "Information Technology - Abstract Syntax Notation One
+ (ASN.1): Parameterization of ASN.1 specifications", ITU-T
+ Recommendation X.683, ISO/IEC 8824-4:2015, August 2015,
+ <https://www.itu.int/rec/T-REC-X.683>.
+
+ [X.690] "Information Technology - ASN.1 encoding rules:
+ Specification of Basic Encoding Rules (BER), Canonical
+ Encoding Rules (CER) and Distinguished Encoding Rules
+ (DER)", ITU-T Recommendation X.690, ISO/IEC 8825-1:2015,
+ August 2015, <https://www.itu.int/rec/T-REC-X.690>.
+
+7.3. Informative References
+
+ [Efail] Poddebniak, D., Dresen, C., Muller, J., Ising, F.,
+ Schinzel, S., Friedberger, S., Somorovsky, J., and J.
+ Schwenk, "Efail: Breaking S/MIME and OpenPGP Email
+ Encryption using Exfiltration Channels",
+ UsenixSecurity 2018, August 2018,
+ <https://www.usenix.org/system/files/conference/
+ usenixsecurity18/sec18-poddebniak.pdf>.
+
+ [FIPS186-2]
+ National Institute of Standards and Technology (NIST),
+ "Digital Signature Standard (DSS) (also with Change
+ Notice 1)", Federal Information Processing Standards
+ Publication 186-2, January 2000,
+ <https://csrc.nist.gov/publications/detail/fips/186/2/
+ archive/2000-01-27>.
+
+ [RFC1866] Berners-Lee, T. and D. Connolly, "Hypertext Markup
+ Language - 2.0", RFC 1866, DOI 10.17487/RFC1866,
+ November 1995, <https://www.rfc-editor.org/info/rfc1866>.
+
+
+
+
+Schaad, et al. Standards Track [Page 52]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ [RFC2268] Rivest, R., "A Description of the RC2(r) Encryption
+ Algorithm", RFC 2268, DOI 10.17487/RFC2268, March 1998,
+ <https://www.rfc-editor.org/info/rfc2268>.
+
+ [RFC2311] Dusse, S., Hoffman, P., Ramsdell, B., Lundblade, L., and
+ L. Repka, "S/MIME Version 2 Message Specification",
+ RFC 2311, DOI 10.17487/RFC2311, March 1998,
+ <https://www.rfc-editor.org/info/rfc2311>.
+
+ [RFC2312] Dusse, S., Hoffman, P., Ramsdell, B., and J. Weinstein,
+ "S/MIME Version 2 Certificate Handling", RFC 2312, DOI
+ 10.17487/RFC2312, March 1998,
+ <https://www.rfc-editor.org/info/rfc2312>.
+
+ [RFC2313] Kaliski, B., "PKCS #1: RSA Encryption Version 1.5",
+ RFC 2313, DOI 10.17487/RFC2313, March 1998,
+ <https://www.rfc-editor.org/info/rfc2313>.
+
+ [RFC2314] Kaliski, B., "PKCS #10: Certification Request Syntax
+ Version 1.5", RFC 2314, DOI 10.17487/RFC2314, March 1998,
+ <https://www.rfc-editor.org/info/rfc2314>.
+
+ [RFC2315] Kaliski, B., "PKCS #7: Cryptographic Message Syntax
+ Version 1.5", RFC 2315, DOI 10.17487/RFC2315, March 1998,
+ <https://www.rfc-editor.org/info/rfc2315>.
+
+ [RFC2630] Housley, R., "Cryptographic Message Syntax", RFC 2630,
+ DOI 10.17487/RFC2630, June 1999,
+ <https://www.rfc-editor.org/info/rfc2630>.
+
+ [RFC2631] Rescorla, E., "Diffie-Hellman Key Agreement Method",
+ RFC 2631, DOI 10.17487/RFC2631, June 1999,
+ <https://www.rfc-editor.org/info/rfc2631>.
+
+ [RFC2632] Ramsdell, B., Ed., "S/MIME Version 3 Certificate
+ Handling", RFC 2632, DOI 10.17487/RFC2632, June 1999,
+ <https://www.rfc-editor.org/info/rfc2632>.
+
+ [RFC2633] Ramsdell, B., Ed., "S/MIME Version 3 Message
+ Specification", RFC 2633, DOI 10.17487/RFC2633, June 1999,
+ <https://www.rfc-editor.org/info/rfc2633>.
+
+ [RFC2785] Zuccherato, R., "Methods for Avoiding the "Small-Subgroup"
+ Attacks on the Diffie-Hellman Key Agreement Method for
+ S/MIME", RFC 2785, DOI 10.17487/RFC2785, March 2000,
+ <https://www.rfc-editor.org/info/rfc2785>.
+
+
+
+
+
+Schaad, et al. Standards Track [Page 53]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ [RFC3218] Rescorla, E., "Preventing the Million Message Attack on
+ Cryptographic Message Syntax", RFC 3218,
+ DOI 10.17487/RFC3218, January 2002,
+ <https://www.rfc-editor.org/info/rfc3218>.
+
+ [RFC3766] Orman, H. and P. Hoffman, "Determining Strengths For
+ Public Keys Used For Exchanging Symmetric Keys", BCP 86,
+ RFC 3766, DOI 10.17487/RFC3766, April 2004,
+ <https://www.rfc-editor.org/info/rfc3766>.
+
+ [RFC3850] Ramsdell, B., Ed., "Secure/Multipurpose Internet Mail
+ Extensions (S/MIME) Version 3.1 Certificate Handling",
+ RFC 3850, DOI 10.17487/RFC3850, July 2004,
+ <https://www.rfc-editor.org/info/rfc3850>.
+
+ [RFC3851] Ramsdell, B., Ed., "Secure/Multipurpose Internet Mail
+ Extensions (S/MIME) Version 3.1 Message Specification",
+ RFC 3851, DOI 10.17487/RFC3851, July 2004,
+ <https://www.rfc-editor.org/info/rfc3851>.
+
+ [RFC3852] Housley, R., "Cryptographic Message Syntax (CMS)",
+ RFC 3852, DOI 10.17487/RFC3852, July 2004,
+ <https://www.rfc-editor.org/info/rfc3852>.
+
+ [RFC4134] Hoffman, P., Ed., "Examples of S/MIME Messages", RFC 4134,
+ DOI 10.17487/RFC4134, July 2005,
+ <https://www.rfc-editor.org/info/rfc4134>.
+
+ [RFC4270] Hoffman, P. and B. Schneier, "Attacks on Cryptographic
+ Hashes in Internet Protocols", RFC 4270,
+ DOI 10.17487/RFC4270, November 2005,
+ <https://www.rfc-editor.org/info/rfc4270>.
+
+ [RFC4949] Shirey, R., "Internet Security Glossary, Version 2",
+ FYI 36, RFC 4949, DOI 10.17487/RFC4949, August 2007,
+ <https://www.rfc-editor.org/info/rfc4949>.
+
+ [RFC5035] Schaad, J., "Enhanced Security Services (ESS) Update:
+ Adding CertID Algorithm Agility", RFC 5035, DOI
+ 10.17487/RFC5035, August 2007,
+ <https://www.rfc-editor.org/info/rfc5035>.
+
+ [RFC5750] Ramsdell, B. and S. Turner, "Secure/Multipurpose Internet
+ Mail Extensions (S/MIME) Version 3.2 Certificate
+ Handling", RFC 5750, DOI 10.17487/RFC5750, January 2010,
+ <https://www.rfc-editor.org/info/rfc5750>.
+
+
+
+
+
+Schaad, et al. Standards Track [Page 54]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ [RFC5751] Ramsdell, B. and S. Turner, "Secure/Multipurpose Internet
+ Mail Extensions (S/MIME) Version 3.2 Message
+ Specification", RFC 5751, DOI 10.17487/RFC5751,
+ January 2010, <https://www.rfc-editor.org/info/rfc5751>.
+
+ [RFC6151] Turner, S. and L. Chen, "Updated Security Considerations
+ for the MD5 Message-Digest and the HMAC-MD5 Algorithms",
+ RFC 6151, DOI 10.17487/RFC6151, March 2011,
+ <https://www.rfc-editor.org/info/rfc6151>.
+
+ [RFC6194] Polk, T., Chen, L., Turner, S., and P. Hoffman, "Security
+ Considerations for the SHA-0 and SHA-1 Message-Digest
+ Algorithms", RFC 6194, DOI 10.17487/RFC6194, March 2011,
+ <https://www.rfc-editor.org/info/rfc6194>.
+
+ [RFC6268] Schaad, J. and S. Turner, "Additional New ASN.1 Modules
+ for the Cryptographic Message Syntax (CMS) and the Public
+ Key Infrastructure Using X.509 (PKIX)", RFC 6268,
+ DOI 10.17487/RFC6268, July 2011,
+ <https://www.rfc-editor.org/info/rfc6268>.
+
+ [RFC6278] Herzog, J. and R. Khazan, "Use of Static-Static Elliptic
+ Curve Diffie-Hellman Key Agreement in Cryptographic
+ Message Syntax", RFC 6278, DOI 10.17487/RFC6278,
+ June 2011, <https://www.rfc-editor.org/info/rfc6278>.
+
+ [RFC7114] Leiba, B., "Creation of a Registry for smime-type
+ Parameter Values", RFC 7114, DOI 10.17487/RFC7114,
+ January 2014, <https://www.rfc-editor.org/info/rfc7114>.
+
+ [RFC7905] Langley, A., Chang, W., Mavrogiannopoulos, N.,
+ Strombergson, J., and S. Josefsson, "ChaCha20-Poly1305
+ Cipher Suites for Transport Layer Security (TLS)",
+ RFC 7905, DOI 10.17487/RFC7905, June 2016,
+ <https://www.rfc-editor.org/info/rfc7905>.
+
+ [SP800-56A]
+ National Institute of Standards and Technology (NIST),
+ "Recommendation for Pair-Wise Key Establishment Schemes
+ Using Discrete Logarithm Cryptography", NIST Special
+ Publication 800-56A Revision 2,
+ DOI 10.6028/NIST.SP.800-56Ar2, May 2013,
+ <https://nvlpubs.nist.gov/nistpubs/SpecialPublications/
+ NIST.SP.800-56Ar2.pdf>.
+
+
+
+
+
+
+
+Schaad, et al. Standards Track [Page 55]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ [SP800-57] National Institute of Standards and Technology (NIST),
+ "Recommendation for Key Management - Part 1: General",
+ NIST Special Publication 800-57 Revision 4,
+ DOI 10.6028/NIST.SP.800-57pt1r4, January 2016,
+ <https://nvlpubs.nist.gov/nistpubs/SpecialPublications/
+ NIST.SP.800-57pt1r4.pdf>.
+
+ [TripleDES]
+ Tuchman, W., "Hellman Presents No Shortcut Solutions to
+ the DES", IEEE Spectrum v. 16, n. 7, pp. 40-41,
+ DOI 10.1109/MSPEC.1979.6368160, July 1979.
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+
+Schaad, et al. Standards Track [Page 56]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+Appendix A. ASN.1 Module
+
+ Note: The ASN.1 module contained herein is unchanged from RFC 5751
+ [SMIMEv2] and RFC 3851 [SMIMEv3.1], with the exception of a change to
+ the preferBinaryInside ASN.1 comment in RFC 3851 [SMIMEv3.1]. If a
+ module is needed that is compatible with current ASN.1 standards, one
+ can be found in [RFC6268]. This module uses the 1988 version
+ of ASN.1.
+
+ SecureMimeMessageV3dot1
+
+ { iso(1) member-body(2) us(840) rsadsi(113549)
+ pkcs(1) pkcs-9(9) smime(16) modules(0) msg-v3dot1(21) }
+
+ DEFINITIONS IMPLICIT TAGS ::=
+
+ BEGIN
+
+ IMPORTS
+
+ -- Cryptographic Message Syntax [CMS]
+ 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 by the S/MIME Working Group.
+
+ id-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 type.
+
+ smimeCapabilities 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.
+
+
+
+Schaad, et al. Standards Track [Page 57]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ id-aa-encrypKeyPref OBJECT IDENTIFIER ::= {id-aa 11}
+
+ SMIMEEncryptionKeyPreference ::= CHOICE {
+ issuerAndSerialNumber [0] IssuerAndSerialNumber,
+ receipentKeyId [1] RecipientKeyIdentifier,
+ subjectAltKeyIdentifier [2] SubjectKeyIdentifier
+ }
+
+ -- "receipentKeyId" is spelled incorrectly but is kept for
+ -- historical reasons.
+
+ id-smime OBJECT IDENTIFIER ::= { iso(1) member-body(2) us(840)
+ rsadsi(113549) pkcs(1) pkcs-9(9) 16 }
+
+ id-cap OBJECT IDENTIFIER ::= { id-smime 11 }
+
+ -- The preferBinaryInside OID indicates an ability to receive
+ -- messages with binary encoding inside the CMS wrapper.
+ -- The preferBinaryInside attribute's value field is ABSENT.
+
+ id-cap-preferBinaryInside OBJECT IDENTIFIER ::= { id-cap 1 }
+
+ -- The following is a list of OIDs to be used with S/MIME v3.
+
+ -- Signature Algorithms Not Found in [RFC3370], [RFC5754], [RFC4056],
+ -- and [RFC3560]
+
+ --
+ -- 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))
+
+ END
+
+
+
+
+
+
+Schaad, et al. Standards Track [Page 58]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+Appendix B. Historic Mail Considerations
+
+ Over the course of updating the S/MIME specifications, the set of
+ recommended algorithms has been modified each time the documents have
+ been updated. This means that if a user has historic emails and
+ their user agent has been updated to only support the current set of
+ recommended algorithms, some of those old emails will no longer be
+ accessible. It is strongly suggested that user agents implement some
+ of the following algorithms for dealing with historic emails.
+
+ This appendix contains a number of references to documents that have
+ been obsoleted or replaced. This is intentional, as the updated
+ documents often do not have the same information in them.
+
+B.1. DigestAlgorithmIdentifier
+
+ The following algorithms have been called out for some level of
+ support by previous S/MIME specifications:
+
+ - SHA-1 was dropped in [SMIMEv4]. SHA-1 is no longer considered to
+ be secure, as it is no longer collision resistant. The IETF
+ statement on SHA-1 can be found in [RFC6194], but it is out of
+ date relative to the most recent advances.
+
+ - MD5 was dropped in [SMIMEv4]. MD5 is no longer considered to be
+ secure, as it is no longer collision resistant. Details can be
+ found in [RFC6151].
+
+B.2. Signature Algorithms
+
+ There are a number of problems with validating signatures on
+ sufficiently historic messages. For this reason, it is strongly
+ suggested that user agents treat these signatures differently from
+ those on current messages. These problems include the following:
+
+ - Certification authorities are not required to keep certificates on
+ a CRL beyond one update after a certificate has expired. This
+ means that unless CRLs are cached as part of the message it is not
+ always possible to check to see if a certificate has been revoked.
+ The same problems exist with Online Certificate Status Protocol
+ (OCSP) responses, as they may be based on a CRL rather than on the
+ certificate database.
+
+
+
+
+
+
+
+
+
+Schaad, et al. Standards Track [Page 59]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+ - RSA and DSA keys of less than 2048 bits are now considered by many
+ experts to be cryptographically insecure (due to advances in
+ computing power). Such keys were previously considered secure, so
+ the processing of historic signed messages will often result in
+ the use of weak keys. Implementations that wish to support
+ previous versions of S/MIME or process old messages need to
+ consider the security risks that result from smaller key sizes
+ (e.g., spoofed messages) versus the costs of denial of service.
+
+ [SMIMEv3.1] set the lower limit on suggested key sizes for
+ creating and validation at 1024 bits. Prior to that, the lower
+ bound on key sizes was 512 bits.
+
+ - Hash functions used to validate signatures on historic messages
+ may no longer be considered to be secure (see below). While there
+ are not currently any known practical pre-image or second
+ pre-image attacks against MD5 or SHA-1, the fact that they are no
+ longer considered to be collision resistant implies that the
+ security levels of the signatures are generally considered
+ suspect. If a message is known to be historic and it has been in
+ the possession of the client for some time, then it might still be
+ considered to be secure.
+
+ - The previous two issues apply to the certificates used to validate
+ the binding of the public key to the identity that signed the
+ message as well.
+
+ The following algorithms have been called out for some level of
+ support by previous S/MIME specifications:
+
+ - RSA with MD5 was dropped in [SMIMEv4]. MD5 is no longer
+ considered to be secure, as it is no longer collision resistant.
+ Details can be found in [RFC6151].
+
+ - RSA and DSA with SHA-1 were dropped in [SMIMEv4]. SHA-1 is no
+ longer considered to be secure, as it is no longer collision
+ resistant. The IETF statement on SHA-1 can be found in [RFC6194],
+ but it is out of date relative to the most recent advances.
+
+ - DSA with SHA-256 was dropped in [SMIMEv4]. DSA has been replaced
+ by elliptic curve versions.
+
+
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+Schaad, et al. Standards Track [Page 60]
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+
+ As requirements for "mandatory to implement" have changed over time,
+ some issues have been created that can cause interoperability
+ problems:
+
+ - 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.
+
+ - 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.
+
+ - Note that S/MIME v3.1 clients support verifying id-dsa-with-sha1
+ and rsaEncryption and might not implement sha256WithRSAEncryption.
+
+ NOTE: Receiving clients SHOULD recognize id-dsa as equivalent to
+ id-dsa-with-sha1.
+
+ For 512-bit RSA with SHA-1, see [RFC3370] and [FIPS186-2] without
+ Change Notice 1; for 512-bit RSA with SHA-256, see [RFC5754] and
+ [FIPS186-2] without Change Notice 1; and for 1024-bit through
+ 2048-bit RSA with SHA-256, see [RFC5754] and [FIPS186-2] with Change
+ Notice 1. The first reference provides the signature algorithm's
+ OID, and the second provides the signature algorithm's definition.
+
+ For 512-bit DSA with SHA-1, see [RFC3370] and [FIPS186-2] without
+ Change Notice 1; for 512-bit DSA with SHA-256, see [RFC5754] and
+ [FIPS186-2] without Change Notice 1; for 1024-bit DSA with SHA-1, see
+ [RFC3370] and [FIPS186-2] with Change Notice 1; and for 1024-bit and
+ above DSA with SHA-256, see [RFC5754] and [FIPS186-4]. The first
+ reference provides the signature algorithm's OID, and the second
+ provides the signature algorithm's definition.
+
+B.3. ContentEncryptionAlgorithmIdentifier
+
+ The following algorithms have been called out for some level of
+ support by previous S/MIME specifications:
+
+ - RC2/40 [RFC2268] was dropped in [SMIMEv3.2]. The algorithm is
+ known to be insecure and, if supported, should only be used to
+ decrypt existing email.
+
+ - DES EDE3 CBC [TripleDES], also known as "tripleDES", was dropped
+ in [SMIMEv4]. This algorithm is removed from the list of
+ supported algorithms because (1) it has a 64-bit block size and
+ (2) it offers less than 128 bits of security. This algorithm
+ should be supported only to decrypt existing email; it should not
+ be used to encrypt new emails.
+
+
+
+Schaad, et al. Standards Track [Page 61]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+B.4. KeyEncryptionAlgorithmIdentifier
+
+ The following algorithms have been called out for some level of
+ support by previous S/MIME specifications:
+
+ - DH ephemeral-static mode, as specified in [RFC3370] and
+ [SP800-57], was dropped in [SMIMEv4].
+
+ - RSA key sizes have been increased over time. Decrypting old mail
+ with smaller key sizes is reasonable; however, new mail should use
+ the updated key sizes.
+
+ For 1024-bit DH, see [RFC3370]. For 1024-bit and larger DH, see
+ [SP800-56A]; regardless, use the KDF, which is from X9.42, specified
+ in [RFC3370].
+
+Appendix C. Moving S/MIME v2 Message Specification to Historic Status
+
+ The S/MIME v3 [SMIMEv3], v3.1 [SMIMEv3.1], and v3.2 [SMIMEv3.2]
+ specifications are backward compatible with the S/MIME v2 Message
+ Specification [SMIMEv2], with the exception of the algorithms
+ (dropped RC2/40 requirement and added DSA and RSASSA-PSS
+ requirements). Therefore, RFC 2311 [SMIMEv2] was moved to Historic
+ status.
+
+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. Without v2, there wouldn't be a v3, v3.1,
+ v3.2, or v4.0.
+
+ Some of the examples in this document were copied from [RFC4134].
+ Thanks go to the people who wrote and verified the examples in that
+ document.
+
+ 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 because they made direct
+ contributions to this document:
+
+ Tony Capel, Piers Chivers, Dave Crocker, Bill Flanigan, Peter
+ Gutmann, Alfred Hoenes, Paul Hoffman, Russ Housley, William Ottaway,
+ and John Pawling.
+
+ The version 4 update to the S/MIME documents was done under the
+ auspices of the LAMPS Working Group.
+
+
+
+Schaad, et al. Standards Track [Page 62]
+
+RFC 8551 S/MIME 4.0 Message Specification April 2019
+
+
+Authors' Addresses
+
+ Jim Schaad
+ August Cellars
+
+ Email: ietf@augustcellars.com
+
+
+ Blake Ramsdell
+ Brute Squad Labs, Inc.
+
+ Email: blaker@gmail.com
+
+
+ Sean Turner
+ sn3rd
+
+ Email: sean@sn3rd.com
+
+
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+Schaad, et al. Standards Track [Page 63]
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