wdiff rfc5751.original rfc5751.txt

S/MIME WG
Network Working Group B. Ramsdell
Internet Draft
Request for Comments: 5751 Brute Squad Labs
Intended Status: Standard Track S. Turner
Obsoletes: 3851 (when approved) S. Turner
Category: Standards Track IECA
Expires: November 12, 2009 May 12,
December 2009

Secure/Multipurpose Internet Mail Extensions (S/MIME) Version 3.2
Message Specification
draft-ietf-smime-3851bis-11.txt

Status of this Memo

Abstract

This Internet-Draft is submitted document defines Secure/Multipurpose Internet Mail Extensions
(S/MIME) version 3.2. S/MIME provides a consistent way to IETF in full conformance send and
receive secure MIME data. Digital signatures provide authentication,
message integrity, and non-repudiation with the
provisions proof of BCP 78 and BCP 79. origin.
Encryption provides data confidentiality. Compression can be used to
reduce data size. 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 obsoletes RFC 3851.

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Abstract

This Code Components extracted from this document defines Secure/Multipurpose Internet Mail Extensions
(S/MIME) version 3.2. S/MIME provides a consistent way to send and
receive secure MIME data. Digital signatures provide authentication,
message integrity, and non-repudiation with proof must
include Simplified BSD License text as described in Section 4.e of origin.
Encryption provides data confidentiality. Compression can be used to
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This document obsoletes RFC 3851.

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Table of Contents

1. Introduction................................................ 3 Introduction ....................................................4
1.1. Specification Overview................................. 4 Overview .....................................4
1.2. Definitions............................................ 5 Definitions ................................................5
1.3. Conventions used Used in this document...................... 5 This Document ..........................6
1.4. Compatibility with Prior Practice of S/MIME............ 6 S/MIME ................7
1.5. Changes From from S/MIME v3 to S/MIME v3.1.................. 6 v3.1 ......................7
1.6. Changes Since since S/MIME v3.1.............................. 7 v3.1 ..................................7
2. CMS Options ................................................ 8 .....................................................9
2.1. DigestAlgorithmIdentifier.............................. 8 DigestAlgorithmIdentifier ..................................9
2.2. SignatureAlgorithmIdentifier .......................... 9 ...............................9
2.3. KeyEncryptionAlgorithmIdentifier....................... 9 KeyEncryptionAlgorithmIdentifier ..........................10
2.4. General Syntax......................................... 10 Syntax ............................................11
2.5. Attributes and the SignerInfo Type .................... 11 ........................12
2.6. SignerIdentifier SignerInfo Type....................... 15 Type ..........................16
2.7. ContentEncryptionAlgorithmIdentifier................... 15 ContentEncryptionAlgorithmIdentifier ......................16
3. Creating S/MIME Messages.................................... 18 Messages .......................................18
3.1. Preparing the MIME Entity for Signing, Enveloping Enveloping,
or
Compressing............................................ 18 Compressing ............................................19
3.2. The application/pkcs7-mime Media Type.................. 22 Type .....................23
3.3. Creating an Enveloped-only Enveloped-Only Message .................... 25 ........................25
3.4. Creating a Signed-only Message......................... 26 Signed-Only Message ............................26
3.5. Creating a Compressed-only Compressed-Only Message .................... 29 ........................30
3.6. Multiple Operations.................................... 30 Operations .......................................30
3.7. Creating a Certificate Management Message.............. 31 Message .................31
3.8. Registration Requests.................................. 31 Requests .....................................32
3.9. Identifying an S/MIME Message.......................... 32 Message .............................32
4. Certificate Processing ..................................... 32 .........................................32
4.1. Key Pair Generation.................................... 32 Generation .......................................33
4.2. Signature Generation................................... 33 Generation ......................................33
4.3. Signature Verification................................. 33 Verification ....................................34
4.4. Encryption............................................. 34 Encryption ................................................34
4.5. Decryption............................................. 34 Decryption ................................................34
5. IANA Considerations......................................... 34 Considerations ............................................34
5.1. Media Type for application/pkcs7-mime.................. 34 application/pkcs7-mime .....................34
5.2. Media Type for application/pkcs7-signature............. 35 application/pkcs7-signature ................35
6. Security Considerations..................................... 36 Considerations ........................................36
7. References.................................................. 38 References .....................................................38
7.1. Normative References................................... 38 Reference Conventions .....................................38
7.2. Normative References ......................................39
7.3. Informative References................................. 40 References ....................................41
Appendix A. ASN.1 Module....................................... 42 Module ..........................................43
Appendix B. Moving S/MIME v2 Message Specification to Historic
Status............................................. 46
Status ................................................45
Appendix C. Acknowledgments.................................... 46
Authors' Addresses............................................. 46 Acknowledgments .......................................45

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 for 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.

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 content type based content-type-based applications.

This specification defines how to create a MIME body part that has
been cryptographically enhanced according to the Cryptographic
Message Syntax (CMS) RFC 3852 and RFC 4853 5652 [CMS], which is derived from PKCS #7
[PKCS-7]. This specification also defines the application/pkcs7-mime
media type that can be used to transport those body parts.

This document also discusses how to use the multipart/signed media
type defined in [MIME-SECURE] 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 the Cryptographic Message Syntax document [CMS], [CMSALG],
[RSAPSS], [RSAOAEP], and [CMS-SHA2].

Throughout this specification, there are requirements and
recommendations made for how receiving agents handle incoming
messages. There are separate requirements and recommendations for
how sending agents create outgoing messages. In general, the best
strategy is to "be liberal in what you receive and conservative in
what you send". Most of the requirements are placed on the handling
of incoming messages 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
Recommendation X.680 [X.680].

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].

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 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
end-of-line delimiter.

Binary data: Arbitrary data.

Transfer Encoding: 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.

1.3. Conventions used Used in this document This Document

The key words "MUST", "MUST NOT", "REQUIRED", "SHALL", "SHALL NOT",
"SHOULD", "SHOULD NOT", "RECOMMENDED", "MAY", and "OPTIONAL" in this
document are to be interpreted as described in [MUSTSHOULD].

We define some additional terms here:

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-.

1.4. Compatibility with Prior Practice of S/MIME

S/MIME version 3.2 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], 5035 [SMIMEv3], and S/MIME version 3.1 is described
in RFC 3850, RFC 3851, RFC 3852, RFC 2634, RFC 4853, and RFC 5035 [SMIMEv3.1].
RFC 2311 also has historical information about the development of
S/MIME.

1.5. Changes From from S/MIME v3 to S/MIME v3.1

The RSA public key algorithm was changed to a MUST implement key
wrapping algorithm, and the Diffie-Hellman (DH) algorithm changed to
a SHOULD implement.

The AES symmetric encryption algorithm has been included as a SHOULD
implement.

The RSA public key algorithm was changed to a MUST implement
signature algorithm.

Ambiguous language about the use of "empty" SignedData messages to
transmit certificates was clarified to reflect that transmission of
certificate revocation lists
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 Since since S/MIME v3.1

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-.

Sec

Section 1.1 and Appendix A: Added references to RFCs for RSASSA-PSS,
RSAES-OAEP, and SHA2 CMS Algorithms. algorithms. Added CMS Multiple Signers
Clarification to CMS reference.

Sec

Section 1.2: Updated references to ASN.1 to X.680 and BER and DER to
X.690.

Sec

Section 1.4: Added references to S/MIME MSG 3.1 RFCs.

Sec

Section 2.1 (digest algorithm): SHA-256 added as MUST, SHA-1 and MD5
made SHOULD-.

Sec

Section 2.2 (signature algorithms): RSA with SHA-256 added as MUST,
and 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.

Sec

Section 2.3 (key encryption): DH changed to SHOULD- SHOULD-, and RSAES-OAEP
added as SHOULD+. Elaborated requirements for key wrap algorithm.

Sec

Section 2.5.1: Added requirement that receiving agents MUST support
both GeneralizedTime and UTCTime.

Sec

Section 2.5.2: Replaced reference "sha1WithRSAEncryption" with
"sha256WithRSAEncryption", "DES-3EDE-CBC" with "AES-128 CBC", and
deleted the RC5 example.

Sec

Section 2.5.2.1: Deleted entire section (discussed deprecated RC2).

Sec

Section 2.7, 2.7.1, Appendix A: references to RC2/40 removed.

Sec

Section 2.7 (content encryption): AES-128 CBC added as MUST, AES-192
and AES-256 CBC SHOULD+, tripleDES now SHOULD-.

Sec

Section 2.7.1: Updated pointers from 2.7.2.1 through 2.7.2.4 to
2.7.1.1 to 2.7.1.2.

Sec

Section 3.1.1: Removed text about MIME character sets.

Sec

Section 3.2.2 and 3.6: Replaced "encrypted" with "enveloped". Update
OID example to use AES-128 CBC oid.

Sec

Section 3.4.3.2: Replace micalg parameter for SHA-1 with sha-1.

Sec

Section 4: Updated reference to CERT v3.2.

Sec

Section 4.1: Updated RSA and DSA key size discussion. Moved last
four sentences to security considerations. Updated reference to
randomness requirements for security.

Sec

Section 5: Added IANA registration templates to update media type
registry to point to this document as opposed to RFC 2311.

Sec

Section 6: Updated Security Considerations.

Sec security considerations.

Section 7: Moved references from Appendix B to this section. Updated
references. Added informational references to SMIMEv2, SMIMEv3, and
SMIMEv3.1.

App

Appendix B: Added Appendix B to move S/MIME v2 to historic Historic status.

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. [CMSALG] and [CMS-
SHA2]
[CMS-SHA2] provides additional details regarding the use of the
cryptographic algorithms. [ESS] provides additional details
regarding the use of additional attributes.

2.1. DigestAlgorithmIdentifier

Sending and receiving agents MUST support SHA-256 [CMS-SHA2] and
SHOULD- support SHA-1 [CMSALG]. Receiving agents SHOULD- support MD5
[CMSALG] for the purpose of providing backward compatibility with
MD5-digested S/MIME v2 SignedData objects.

2.2. SignatureAlgorithmIdentifier

Receiving agents:

- MUST support RSA with SHA-256 SHA-256.

- SHOULD+ support DSA with SHA-256 SHA-256.

- SHOULD+ support RSASSA-PSS with SHA-256 SHA-256.

- SHOULD- support RSA with SHA-1 SHA-1.

- SHOULD- support DSA with SHA-1 SHA-1.

- SHOULD- support RSA with MD5.

Sending agents:

- MUST support RSA with SHA-256 SHA-256.

- SHOULD+ support DSA with SHA-256 SHA-256.

- SHOULD+ support RSASSA-PSS with SHA-256 SHA-256.

- SHOULD- support RSA with SHA-1 or DSA with SHA-1 SHA-1.

- SHOULD- support RSA with MD5.

See section Section 4.1 for information on key size and algorithm references.

Note that S/MIME v3.1 clients support verifying id-dsa-with-sha1 and
rsaEncryption and might not implement sha256withRSAEncryption. Note
that S/MIME v3 clients might only implement signing or signature
verification using id-dsa-with-sha1, and might also use id-dsa as an
AlgorithmIdentifier in this field. Receiving clients SHOULD
recognize id-dsa as equivalent to id-dsa-with-sha1, and sending
clients MUST use id-dsa-with-sha1 if using that algorithm. Also note
that S/MIME v2 clients are only required to verify digital signatures
using the rsaEncryption algorithm with SHA-1 or MD5, and might not
implement id-dsa-with-sha1 or id-dsa at all.

2.3. KeyEncryptionAlgorithmIdentifier

Receiving and sending agents:

- MUST support RSA Encryption, as specified in [CMSALG] [CMSALG].

- SHOULD+ support RSAES-OAEP, as specified in [RSAOAEP] [RSAOAEP].

- SHOULD- support DH ephemeral-static mode, as specified in
[CMSALG] and [SP800-57].

When DH ephemeral-static is used, a key wrap algorithm is also
specified in the KeyEncryptionAlgorithmIdentifier [CMS]. The
underlying encryption functions for the key wrap and content
encryption algorithm ([CMSALG] and [CMSAES]) and the key sizes for
the two algorithms MUST be the same (e.g., AES-128 key wrap algorithm
with AES 128 AES-128 content encryption algorithm). As AES 128 AES-128 CBC is the
mandatory to implement
mandatory-to-implement content encryption algorithm, the AES-128 key
wrap algorithm MUST also be supported when DH ephemeral-static is
used.

Note that S/MIME v3.1 clients might only implement key encryption and
decryption using the rsaEncryption algorithm. Note that S/MIME v3
clients might only implement key encryption and decryption using the
Diffie-Hellman algorithm. Also note that S/MIME v2 clients are only
capable of decrypting content-encryption keys using the rsaEncryption
algorithm.

2.4. General Syntax

There are several CMS content types. Of these, only the Data,
SignedData, EnvelopedData, and CompressedData content types are
currently used for S/MIME.

2.4.1. Data Content Type

Sending agents MUST use the id-data content type identifier to
identify the "inner" MIME message content. For example, when
applying a digital signature to MIME data, the CMS SignedData
encapContentInfo eContentType MUST include the id-data object
identifier and the 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
Section 3.4.3 of this document). As another example, when applying
encryption to MIME data, the CMS EnvelopedData encryptedContentInfo
contentType MUST include the id-data object identifier and the
encrypted MIME content MUST be stored in the EnvelopedData
encryptedContentInfo encryptedContent OCTET STRING.

2.4.2. SignedData Content Type

Sending agents MUST use the SignedData content type to apply a
digital signature to a message or, in a degenerate case where there
is no signature information, to convey certificates. Applying a
signature to a message provides authentication, message integrity,
and non-repudiation of origin.

2.4.3. EnvelopedData Content Type

This content type is used to apply data confidentiality to a message.
A sender needs to have access to a public key for each intended
message recipient to use this service.

2.4.4. CompressedData Content Type

This content type is used to apply data compression to a message.
This content type does not provide authentication, message integrity,
non-repudiation, or data confidentiality, and is only used to reduce
the message's size.

See section Section 3.6 for further guidance on the use of this type in
conjunction with other CMS types.

2.5. Attributes and the SignerInfo Type

The SignerInfo type allows the inclusion of unsigned and signed
attributes along with a signature.

Receiving agents MUST be able to handle zero or one instance of each
of the signed attributes listed here. Sending agents SHOULD generate
one instance of each of the following signed attributes in each
S/MIME message:

- signingTime Signing Time (section (Section 2.5.1 in this document)

- sMIMECapabilities SMIME Capabilities (section (Section 2.5.2 in this document)

- sMIMEEncryptionKeyPreference Encryption Key Preference (section (Section 2.5.3 in this
document)

- id-messageDigest Message Digest (section (Section 11.2 in [CMS])

- id-contentType Content Type (section (Section 11.1 in [CMS])

Further, receiving agents SHOULD be able to handle zero or one
instance of the signingCertificate and signingCertificatev2 signed
attributes, as defined in section Section 5 of RFC 2634 [ESS] and section Section 3
of RFC 5035 [ESS].

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 Signing Time Attribute

The signing-time attribute is used to convey the time that a message
was signed. The time of signing will most likely be created by a
message originator and therefore is only as trustworthy as the
originator.

Sending agents MUST encode signing time through the year 2049 as
UTCTime; signing times in 2050 or later MUST be encoded as
GeneralizedTime. When the UTCTime CHOICE is used, S/MIME agents MUST
interpret the year field (YY) as follows:

If YY is greater than or equal to 50, the year is interpreted as
19YY; if YY is less than 50, the year is interpreted as 20YY.

Receiving agents MUST be able to process signing-time attributes that
are encoded in either UTCTime or GeneralizedTime.

2.5.2. SMIMECapabilities SMIME Capabilities Attribute

The SMIMECapabilities attribute includes signature algorithms (such
as "sha256WithRSAEncryption"), symmetric algorithms (such as "AES-128
CBC"), and key encipherment algorithms (such as "rsaEncryption").
There are also several identifiers which that indicate support for other
optional features such as binary encoding and compression. The
SMIMECapabilities were designed to be flexible and extensible so
that, in the future, a means of identifying other capabilities and
preferences such as certificates can be added in a way that will not
cause current clients to break.

If present, the SMIMECapabilities attribute MUST be a
SignedAttribute; it MUST NOT be an UnsignedAttribute. CMS defines
SignedAttributes as a SET OF Attribute. The SignedAttributes in a
signerInfo MUST NOT include multiple instances of the
SMIMECapabilities attribute. CMS defines the ASN.1 syntax for
Attribute to include attrValues SET OF AttributeValue. A
SMIMECapabilities attribute MUST only include a single instance of
AttributeValue. There MUST NOT be zero or multiple instances of
AttributeValue present in the attrValues SET OF AttributeValue.

The semantics of the SMIMECapabilities attribute specify a partial
list as to what the client announcing the SMIMECapabilities can
support. A client does not have to list every capability it
supports, and need not list all its capabilities so that the
capabilities list doesn't get too long. In an SMIMECapabilities
attribute, the object identifiers (OIDs) are listed in order of their
preference, but SHOULD be separated logically along the lines of
their categories (signature algorithms, symmetric algorithms, key
encipherment algorithms, etc.) etc.).

The structure of the SMIMECapabilities attribute is to facilitate
simple table lookups and binary comparisons in order to determine
matches. For instance, the DER-encoding for the SMIMECapability for
AES-128 CBC MUST be identically encoded regardless of the
implementation. Because of the requirement for identical encoding,
individuals documenting algorithms to be used in the
SMIMECapabilities attribute SHOULD explicitly document the correct
byte sequence for the common cases.

For any capability, the associated parameters for the OID MUST
specify all of the parameters necessary to differentiate between two
instances of the same algorithm.

The OIDs that correspond to algorithms SHOULD use the same OID as the
actual algorithm, except in the case where the algorithm usage is
ambiguous from the OID. For instance, in an earlier specification,
rsaEncryption was ambiguous because it could refer to either a
signature algorithm or a key encipherment algorithm. In the event
that an OID is ambiguous, it needs to be arbitrated by the maintainer
of the registered SMIMECapabilities list as to which type of
algorithm will use the OID, and a new OID MUST be allocated under the
smimeCapabilities OID to satisfy the other use of the OID.

The registered SMIMECapabilities list specifies the parameters for
OIDs that need them, most notably key lengths in the case of
variable-length symmetric ciphers. In the event that there are no
differentiating parameters for a particular OID, the parameters MUST
be omitted, and MUST NOT be encoded as NULL. Additional values for
the SMIMECapabilities attribute might be defined in the future.
Receiving agents MUST handle a SMIMECapabilities object that has
values that it does not recognize in a graceful manner.

Section 2.7.1 explains a strategy for caching capabilities.

2.5.3. Encryption Key Preference Attribute

The encryption key preference attribute allows the signer to
unambiguously describe which of the signer's certificates has the
signer's preferred encryption key. This attribute is designed to
enhance behavior for interoperating with those clients that use
separate keys for encryption and signing. This attribute is used to
convey to anyone viewing the attribute which of the listed
certificates is appropriate for encrypting a session key for future
encrypted messages.

If present, the SMIMEEncryptionKeyPreference attribute MUST be a
SignedAttribute; it MUST NOT be an UnsignedAttribute. CMS defines
SignedAttributes as a SET OF Attribute. The SignedAttributes in a
signerInfo MUST NOT include multiple instances of the
SMIMEEncryptionKeyPreference attribute. CMS defines the ASN.1 syntax
for Attribute to include attrValues SET OF AttributeValue. A
SMIMEEncryptionKeyPreference attribute MUST only include a single
instance of AttributeValue. There MUST NOT be zero or multiple
instances of AttributeValue present in the attrValues SET OF
AttributeValue.

The sending agent SHOULD include the referenced certificate in the
set of certificates included in the signed message if this attribute
is used. The certificate MAY be omitted if it has been previously
made available to the receiving agent. Sending agents SHOULD use
this attribute if the commonly used or preferred 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 a X.509 certificate with
the same subject name as the signer of a X.509 certificate
which that can
be used for key management.

- Or use some other method of determining the user's key management
key. If a X.509 key management certificate is not found, then
encryption cannot be done with the signer of the message. If
multiple X.509 key management certificates are found, the S/MIME
agent can make an arbitrary choice between them.

2.6. SignerIdentifier SignerInfo Type

S/MIME v3.2 implementations MUST support both issuerAndSerialNumber
as well as
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 CBC [CMSAES]
[CMSAES].

- SHOULD+ support encryption and decryption with AES-192 CBC and
AES-256 CBC [CMSAES] [CMSAES].

- SHOULD- support encryption and decryption with DES EDE3 CBC,
hereinafter called "tripleDES" [CMSALG].

2.7.1. Deciding Which Encryption Method To to Use

When a sending agent creates an encrypted message, it has to decide
which type of encryption to use. The decision process involves using
information garnered from the capabilities lists included in messages
received from the recipient, as well as out-of-band information such
as private agreements, user preferences, legal restrictions, and so
on.

Section 2.5.2 defines a method by which a sending agent can
optionally announce, among other things, its decrypting capabilities
in its order of preference. The following method for processing and
remembering the encryption capabilities attribute in incoming signed
messages SHOULD be used.

- If the receiving agent has not yet created a list of
capabilities for the sender's public key, then, after verifying
the signature on the incoming message and checking the
timestamp, the receiving agent SHOULD create a new list
containing at least the signing time and the symmetric
capabilities.

- If such a list already exists, the receiving agent SHOULD verify
that the signing time in the incoming message is greater than
the signing time stored in the list and that the signature is
valid. If so, the receiving agent SHOULD update both the
signing time and capabilities in the list. Values of the
signing time that lie far in the future (that is, a greater
discrepancy than any reasonable clock skew), or a capabilities
list in messages whose signature could not be verified, MUST NOT
be accepted.

The list of capabilities SHOULD be stored for future use in creating
messages.

Before sending a message, the sending agent MUST decide whether it is
willing to use weak encryption for the particular data in 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 through 2.7.1.2 describe the decisions a sending
agent SHOULD use in deciding which type of encryption will be applied
to a message. These rules are ordered, so the sending agent SHOULD
make its decision in the order given.

2.7.1.1. Rule 1: Known Capabilities

If the sending agent has received a set of capabilities from the
recipient for the message the agent is about to encrypt, then the
sending agent SHOULD use that information by selecting the first
capability in the list (that is, the capability most preferred by the
intended recipient) that the sending agent knows how to encrypt. The
sending agent SHOULD use one of the capabilities in the list if the
agent reasonably expects the recipient to be able to decrypt the
message.

2.7.1.2. Rule 2: Unknown Capabilities, Unknown Version of S/MIME

If the following two conditions are met:

- the sending agent has no knowledge of the encryption
capabilities of the recipient, and

- the sending agent has no knowledge of the version of S/MIME of
the recipient,
then the sending agent SHOULD use AES-128 because it is a stronger
algorithm and is required by S/MIME v3.2. If the sending agent
chooses not to use AES-128 in this step, it SHOULD use tripleDES.

2.7.2. Choosing Weak Encryption

All algorithms that use 40 bit 40-bit keys are considered by many to be weak
encryption. A sending agent that is controlled by a human SHOULD
allow a human sender to determine the risks of sending data using a
weak encryption algorithm before sending the data, and possibly allow
the human to use a stronger encryption method such as tripleDES or
AES.

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- strongly
encrypted message simply by decrypting the weakly-encrypted 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 which that
produce a CMS object. Finally, the CMS object is wrapped in MIME.
The Enhanced Security Services for S/MIME [ESS] document provides
descriptions of how nested, secured S/MIME messages are formatted.
ESS provides a description of how a triple-wrapped S/MIME message is
formatted using multipart/signed and application/pkcs7-mime for the
signatures.

S/MIME provides one format for enveloped-only data, several formats
for signed-only data, and several formats for signed and enveloped
data. Several formats are required to accommodate several
environments, in particular for signed messages. The criteria for
choosing among these formats are also described.

The reader of this section is expected to understand MIME as
described in [MIME-SPEC] and [MIME-SECURE].

3.1. Preparing the MIME Entity for Signing, Enveloping Enveloping, or Compressing

S/MIME is used to secure MIME entities. A MIME entity can be a sub-
part, sub-parts of a message, or the whole message with all its sub-
parts. A MIME entity that is the whole message includes only the
MIME message headers and MIME body, and does not include the RFC-822
header. Note that S/MIME can also be used to secure MIME entities
used in applications other than Internet mail. If protection of the
RFC-822 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 content types is
described in Section Sections 3.2, 3.4, and elsewhere.

The procedure for preparing a MIME entity is given in [MIME-SPEC].
The same procedure is used here with some additional restrictions
when signing. Description The description of the procedures from [MIME-SPEC] are is
repeated here, but it is suggested that the reader refer to that
document for the exact procedure. This section also describes
additional requirements.

A single procedure is used for creating MIME entities that are to
have any combination of signing, enveloping, and compressing applied.
Some additional steps are recommended to defend against known
corruptions that can occur during mail transport that are of
particular importance for clear-signing using the multipart/signed
format. It is recommended that these additional steps be performed
on enveloped messages, or signed and enveloped messages, so that the
message can be forwarded to any environment without modification.

These steps are descriptive rather than prescriptive. The
implementer is free to use any procedure as long as the result is the
same.

Step 1. The MIME entity is prepared according to the local
conventions.

Step 2. The leaf parts of the MIME entity are converted to canonical
form.

Step 3. Appropriate transfer encoding is applied to the leaves of
the MIME entity.

When an S/MIME message is received, the security services on the
message are processed, and the result is the MIME entity. That MIME
entity is typically passed to a MIME-capable user agent where it is
further decoded and presented to the user or receiving application.

In order to protect outer, non-content related non-content-related message header fields
(for instance, the "Subject", "To", "From" "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.

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 which that can be considered their canonical representation.
In general, canonicalization will be performed by the non-security
part of the sending agent rather than the S/MIME implementation.

The most common and important canonicalization is for text, which is
often represented differently in different environments. MIME
entities of major type "text" MUST have both their line endings and
character set canonicalized. The line ending MUST be the pair of
characters <CR><LF>, and the charset SHOULD be a registered charset
[CHARSETS]. The details of the canonicalization are specified in
[MIME-SPEC].

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.

S/MIME implementations SHOULD however use transfer encoding described
in section Section 3.1.3 for all MIME entities they secure. The reason for
securing only 7-bit MIME entities, even for enveloped data that are
not exposed to the transport, is that it allows the MIME entity to be
handled in any environment without changing it. For example, a
trusted gateway might remove the envelope, but not the signature, of
a message, and then forward the signed message on to the 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.

S/MIME implementations which that "know" that all intended recipient(s) recipients are
capable of handling inner (all but the outermost) binary MIME objects
SHOULD use binary encoding as opposed to a 7-bit-safe transfer
encoding for the inner entities. The use of a 7-bit-safe encoding
(such as base64) would unnecessarily expand the message size.
Implementations MAY "know" that recipient implementations are capable
of handling inner binary MIME entities either by interpreting the
id-cap-preferBinaryInside sMIMECapabilities SMIMECapabilities attribute, by prior
agreement, or by other means.

If one or more intended recipients are unable to handle inner binary
MIME objects, or if this capability is unknown for any of the
intended recipients, S/MIME implementations SHOULD use transfer
encoding described in section 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 7-bit
data already need no transfer encoding. Entities such as 8-bit text
and binary data can be encoded with quoted-printable or base-64
transfer encoding.

The primary reason for the 7-bit requirement is that the Internet
mail transport infrastructure cannot guarantee transport of 8-bit or
binary data. Even though many segments of the transport
infrastructure now handle 8-bit and even binary data, it is sometimes
not possible to know whether the transport path is 8-bit clean. If a
mail message with 8-bit data were to encounter a message transfer
agent that can not 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.

[MIME-SECURE] prohibits an agent from changing the transfer encoding
of the first part of a multipart/signed message. If a compliant
agent that can not cannot transmit 8-bit or binary data encounters a
multipart/signed message with 8-bit or binary data in the first part,
it would have to return the message to the sender as undeliverable.

3.1.4. Sample Canonical MIME Entity

This example shows a multipart/mixed message with full transfer
encoding. This message contains a text part and an attachment. The
sample message text includes characters that are not US-ASCII and
thus need to be transfer encoded. Though not shown here, the end of
each line is <CR><LF>. The line ending of the MIME headers, the
text, and the transfer encoded parts, all MUST be <CR><LF>.

Note that this example is not of an S/MIME message.

Content-Type: multipart/mixed; boundary=bar

--bar
Content-Type: text/plain; charset=iso-8859-1
Content-Transfer-Encoding: quoted-printable

=A1Hola Michael!

How do you like the new S/MIME specification?

It's generally a good idea to encode lines that begin with
From=20because some mail transport agents will insert a greater-
than (>) sign, thus invalidating the signature.

Also, in some cases it might be desirable to encode any =20
trailing whitespace that occurs on lines in order to ensure =20
that the message signature is not invalidated when passing =20
a gateway that modifies such whitespace (like BITNET). =20

--bar
Content-Type: image/jpeg
Content-Transfer-Encoding: base64

iQCVAwUBMJrRF2N9oWBghPDJAQE9UQQAtl7LuRVndBjrk4EqYBIb3h5QXIX/LC//
jJV5bNvkZIGPIcEmI5iFd9boEgvpirHtIREEqLQRkYNoBActFBZmh9GC3C041WGq
uMbrbxc+nIs1TIKlA08rVi9ig/2Yh7LFrK5Ein57U/W72vgSxLhe/zhdfolT9Brn
HOxEa44b+EI=

--bar--

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 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 base-64
transfer encoding is appropriate, in particular, when used with SMTP
transport. The transfer encoding used depends on the transport
through which the object is to be sent, and is not a characteristic
of the 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 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 the application/pkcs7-mime, sending agents SHOULD emit the
optional "name" parameter to the Content-Type field for compatibility
with older systems. Sending agents SHOULD also emit the optional
Content-Disposition field [CONTDISP] with the "filename" parameter.
If a sending agent emits the above parameters, the value of the
parameters SHOULD be a file name with the appropriate extension:

Media Type File Extension
application/pkcs7-mime (SignedData, EnvelopedData) .p7m
application/pkcs7-mime (degenerate SignedData .p7c
certificate management message)
application/pkcs7-mime (CompressedData) .p7z
application/pkcs7-signature (SignedData) .p7s

In addition, the file name SHOULD be limited to eight characters
followed by a three letter three-letter extension. The eight character eight-character filename
base can be any distinct name; the use of the filename base "smime"
SHOULD be used to indicate that the MIME entity is associated with
S/MIME.

Including a file name serves two purposes. It facilitates easier use
of S/MIME objects as files on disk. It also can convey type
information across gateways. When a MIME entity of type
application/pkcs7-mime (for example) arrives at a gateway that has no
special knowledge of S/MIME, it will default the entity's media type
to application/octet-stream and treat it as a generic attachment,
thus losing the type information. However, the suggested filename
for an attachment is often carried across a gateway. This often
allows the receiving systems to determine the appropriate application
to hand the attachment off to, in this case, a stand-alone S/MIME
processing application. Note that this mechanism is provided as a
convenience for implementations in certain environments. A proper
S/MIME implementation MUST use the media types and MUST NOT rely on
the file extensions.

3.2.2. The smime-type parameter 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 Type Inner Content
enveloped-data EnvelopedData id-data
signed-data SignedData id-data
certs-only SignedData none
compressed-data CompressedData id-data

In order for consistency to be obtained with future specifications,
the following guidelines SHOULD be followed when assigning a new
smime-type parameter.

1. If both signing and encryption can be applied to the content,
then two values for smime-type SHOULD be assigned "signed-*"
and "enveloped-*". If one operation can be assigned assigned, then this
can be omitted. Thus 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" or
"enveloped" without having to tunnel into the CMS payload.

3.3. Creating an Enveloped-only Enveloped-Only Message

This section describes the format for enveloping a MIME entity
without signing it. It is important to note that sending enveloped
but not signed messages does not provide for data integrity. It is
possible to replace ciphertext in such a way that the processed
message will still be valid, but the meaning can be altered.

Step 1. The MIME entity to be enveloped is prepared according to
section
Section 3.1.

Step 2. The MIME entity and other required data is processed into a
CMS object of type EnvelopedData. In addition to encrypting
a copy of the content-encryption key for each recipient, a
copy of the content-encryption key SHOULD be encrypted for
the originator and included in the EnvelopedData (see [CMS] [CMS],
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; smime-type=enveloped-data;
name=smime.p7m
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename=smime.p7m

rfvbnj756tbBghyHhHUujhJhjH77n8HHGT9HG4VQpfyF467GhIGfHfYT6
7n8HHGghyHhHUujhJh4VQpfyF467GhIGfHfYGTrfvbnjT6jH7756tbB9H
f8HHGTrfvhJhjH776tbB9HG4VQbnj7567GhIGfHfYT6ghyHhHUujpfyF4
0GhIGfHfQbnj756YT64V

3.4. Creating a Signed-only Signed-Only Message

There are two formats for signed messages defined for S/MIME:

- application/pkcs7-mime with SignedData; and, SignedData.

- multipart/signed.

In general, the multipart/signed form is preferred for sending, and
receiving agents MUST be able to handle both.

3.4.1. Choosing a Format for Signed-only Signed-Only Messages

There are no hard-and-fast rules as to when a particular signed-only
format is chosen because it 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 or not. 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 which that would break the signature.

3.4.2. Signing Using application/pkcs7-mime with SignedData

This signing format uses the application/pkcs7-mime media type. The
steps to create this format are:

Step 1. The MIME entity is prepared according to section Section 3.1.

Step 2. The MIME entity and other required data is 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".

A sample message would be:

Content-Type: application/pkcs7-mime; smime-type=signed-data;
name=smime.p7m
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename=smime.p7m

567GhIGfHfYT6ghyHhHUujpfyF4f8HHGTrfvhJhjH776tbB9HG4VQbnj7
77n8HHGT9HG4VQpfyF467GhIGfHfYT6rfvbnj756tbBghyHhHUujhJhjH
HUujhJh4VQpfyF467GhIGfHfYGTrfvbnjT6jH7756tbB9H7n8HHGghyHh
6YT64V0GhIGfHfQbnj75

3.4.3. Signing Using the multipart/signed Format

This format is a clear-signing format. Recipients without any S/MIME
or CMS processing facilities are able to view the message. It makes
use of the multipart/signed media type described in [MIME-SECURE].
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.

3.4.3.1. 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".

3.4.3.2. Creating a multipart/signed Message

Step 1. The MIME entity to be signed is prepared according to
section
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 Section 3.1.

Step 4. Transfer encoding is applied to the "detached signature" CMS
SignedData object object, and it is inserted into a MIME entity of
type application/pkcs7-signature.

Step 5. The MIME entity of the application/pkcs7-signature is
inserted into the second part of the multipart/signed
entity.

The multipart/signed Content-Type has two required parameters: the
protocol parameter and the micalg parameter.

The protocol parameter MUST be "application/pkcs7-signature". Note
that quotation marks are required around the protocol parameter
because MIME requires that the "/" character in the parameter value
MUST be quoted.

The micalg parameter allows for one-pass processing when the
signature is being verified. The value of the micalg parameter is
dependent on the message digest algorithm(s) used in the calculation
of the Message Integrity Check. If multiple message digest
algorithms are used used, they MUST be separated by commas per [MIME-
SECURE]. The values to be placed in the micalg parameter SHOULD be
from the following:

Algorithm Value used 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 algorithm profile or "unknown"
if not defined)

(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 names for this
parameter will be consistent with the IANA "Hash Function Textual
Names" registry.

3.4.3.3. Sample multipart/signed Message

Content-Type: multipart/signed;
protocol="application/pkcs7-signature";
micalg=sha1; boundary=boundary42

--boundary42
Content-Type: text/plain

This is a clear-signed message.

--boundary42
Content-Type: application/pkcs7-signature; name=smime.p7s
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename=smime.p7s

ghyHhHUujhJhjH77n8HHGTrfvbnj756tbB9HG4VQpfyF467GhIGfHfYT6
4VQpfyF467GhIGfHfYT6jH77n8HHGghyHhHUujhJh756tbB9HGTrfvbnj
n8HHGTrfvhJhjH776tbB9HG4VQbnj7567GhIGfHfYT6ghyHhHUujpfyF4
7GhIGfHfYT64VQbnj756

--boundary42--

The content that is digested (the first part of the multipart/signed)
are
consists of the bytes:

43 6f 6e 74 65 6e 74 2d 54 79 70 65 3a 20 74 65 78 74 2f 70 6c 61 69
6e 0d 0a 0d 0a 54 68 69 73 20 69 73 20 61 20 63 6c 65 61 72 2d 73 69
67 6e 65 64 20 6d 65 73 73 61 67 65 2e 0d 0a

3.5. Creating a Compressed-only 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 [CMSCOMPR] and is the preferred method for
compatibility.

Step 1. The MIME entity to be compressed is prepared according to section
Section 3.1.

Step 2. The MIME entity and other required data is are processed into a
CMS object of type CompressedData.

Step 3. The CompressedData object is wrapped in a CMS ContentInfo
object.

Step 4. The ContentInfo object is inserted into an
application/pkcs7-mime MIME entity.

The smime-type parameter for compressed-only messages is "compressed-
data". The file extension for this type of message is ".p7z".

A sample message would be:

Content-Type: application/pkcs7-mime; smime-type=compressed-data;
name=smime.p7z
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename=smime.p7z

rfvbnj756tbBghyHhHUujhJhjH77n8HHGT9HG4VQpfyF467GhIGfHfYT6
7n8HHGghyHhHUujhJh4VQpfyF467GhIGfHfYGTrfvbnjT6jH7756tbB9H
f8HHGTrfvhJhjH776tbB9HG4VQbnj7567GhIGfHfYT6ghyHhHUujpfyF4
0GhIGfHfQbnj756YT64V

3.6. 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 were where automatic signature verification is desired, as no
private key material is required to verify a signature.

There are security ramifications to choosing whether to sign first or
encrypt first. A recipient of a message that is encrypted and then
signed can validate that the encrypted block was unaltered, but
cannot determine any relationship between the signer and the
unencrypted contents of the message. A recipient of a message that
is signed-then-encrypted signed then encrypted can assume that the signed message itself
has not been altered, but that a careful attacker could have changed
the unauthenticated portions of the encrypted message.

When using compression, keep the following guidelines in mind:

- Compression of binary encoded encrypted data is discouraged,
since it will not yield significant compression. Base64
encrypted data could very well benefit, however.

- If a lossy compression algorithm is used with signing, you will
need to compress first, then sign.

3.7. Creating a Certificate Management Message

The certificate management message or MIME entity is used to
transport certificates and/or certificate revocation lists, Certificate Revocation Lists, such as
in response to a registration request.

Step 1. The certificates and/or certificate revocation lists Certificate Revocation Lists are
made available to the CMS generating process which that creates a
CMS object of type SignedData. The SignedData
encapContentInfo eContent field MUST be absent and
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 application/pkcs7-
mime MIME entity.

The smime-type parameter for a certificate management message is
"certs-only". The file extension for this type of message is ".p7c".

3.8. Registration Requests

A sending agent that signs messages MUST have a certificate for the
signature so that a receiving agent can verify the signature. There
are many ways of getting certificates, such as through an exchange
with a certificate 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 v3.2 does not
require a particular certificate request mechanism.

3.9. Identifying an S/MIME Message

Because S/MIME takes into account interoperation in non-MIME
environments, several different mechanisms are employed to carry the
type information, and it becomes a bit difficult to identify S/MIME
messages. The following table lists criteria for determining whether
or not a message is an S/MIME message. A message is considered an
S/MIME message if it matches any of the criteria listed below.

The file suffix in the table below comes from the "name" parameter in
the Content-Type header field, or the "filename" parameter on the
Content-Disposition header field. These parameters that give the
file suffix are not listed below as part of the parameter section.

Media type: application/pkcs7-mime
parameters: any
file suffix: any

Media type: multipart/signed
parameters: protocol="application/pkcs7-signature"
file suffix: any

Media type: application/octet-stream
parameters: any
file suffix: 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
[CERT32].

At a minimum, for initial S/MIME deployment, a user agent could
automatically generate a message to an intended recipient requesting
that recipient's certificate in a signed return message. Receiving
and sending agents SHOULD also provide a mechanism to allow a user to
"store and protect" certificates for correspondents in such a way so
as to guarantee their later retrieval.

4.1. Key Pair Generation

All generated key pairs MUST be generated from a good source of non-
deterministic random input [RANDOM] and the private key MUST be
protected in a secure fashion.

An S/MIME user agent MUST NOT generate asymmetric keys less than 512
bits for use with the RSA or DSA signature algorithms.

For 512-bit RSA with SHA-1 see [CMSALG] and [FIPS186-2] without
Change Notice 1, for 512-bit RSA with SHA-256 see [CMS-SHA2] and
[FIPS186-2] without Change Notice 1, and for 1024-bit through 2048-bit 2048-
bit RSA with SHA-256 see [CMS-SHA2] and [FIPS186-2] with Change
Notice 1. The first reference provides the signature algorithm's
object
identifier identifier, and the second provides the signature algorithm's
definition.

For 512-bit DSA with SHA-1 see [CMSALG] and [FIPS186-2] without
Change Notice 1, for 512-bit DSA with SHA-256 see [CMS-SHA2] and
[FIPS186-2] without Change Notice 1, for 1024-bit DSA with SHA-1 see
[CMSALG] and [FIPS186-2] with Change Notice 1, for 1024-bit and above
DSA with SHA-256 see [CMS-SHA2] and [FIPS186-3]. The first reference
provides the signature algorithm's object identifier and the second
provides the signature algorithm's definition.

For RSASSA-PSS with SHA-256 SHA-256, see [RSAPSS]. For DH 1024-bit DH, see
[CMSALG]. For
RSAES-OAEP 1024-bit and larger DH, see [SP800-56A]; regardless,
use the KDF, which is from X9.42, specified in [CMSALG]. For RSAES-
OAEP, see [RSAOAEP].

4.2. Signature Generation

The following are the requirements for an S/MIME agent generated RSA,
RSASSA-PSS, and DSA signatures:

key size <= 1023 : SHOULD NOT (see Security Considerations)
1024 <= key size <= 2048 : SHOULD (see Security Considerations)
2048 < key size : MAY (see Security Considerations)

4.3. Signature Verification

The following are the requirements for S/MIME receiving agents during
signature verification of RSA, RSASSA-PSS, and DSA signatures:

key size <= 1023 : MAY (see Security Considerations)
1024 <= key size <= 2048 : MUST (see Security Considerations)
2048 < key size : MAY (see Security Considerations)

4.4. Encryption

The following are the requirements for an S/MIME agent when
establishing keys for content encryption using the RSA, RSA-OAEP, and
DH algorithms:

key size <= 1023 : SHOULD NOT (see Security Considerations)
1024 <= key size <= 2048 : SHOULD (see Security Considerations)
2048 < key size : MAY (see Security Considerations)

4.5. Decryption

The following are the requirements for an S/MIME agent when
establishing keys for content decryption using the RSA, RSAES-OAEP,
and DH algorithms:

key size <= 1023 : MAY (see Security Considerations)
1024 <= key size <= 2048 : MUST (see Security Considerations)
2048 < key size : MAY (see Security Considerations)

5. IANA Considerations

The following is intended to provide sufficient information to update updates the media type registration for
application/pkcs7-mime and application/pkcs7-signature to refer to
this document as opposed to RFC 2311.

Note that other documents can define additional MIME media types for
S/MIME.

5.1. Media Type for application/pkcs7-mime

Type name: application

Subtype Name: pkcs7-mime

Required Parameters: NONE
Optional Parameters: smime-type/signed-data
smime-type/enveloped-data
smime-type/compressed-data
smime-type/certs-only
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, and this document

Applications that use this media type: Security applications

Additional information: NONE

Person & email to contact for further information:
S/MIME working group chairs smime-chairs@tools.ietf.org

Intended usage: COMMON

Restrictions on usage: NONE

Author: Sean Turner

Change Controller: S/MIME working group delegated from the IESG

5.2. Media Type for application/pkcs7-signature

Type name: application

Subtype Name: pkcs7-signature

Required Parameters: NONE

Optional Parameters: NONE

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, and this document

Applications that use this media type: Security applications
Additional information: NONE

Person & email to contact for further information:
S/MIME working group chairs smime-chairs@tools.ietf.org

Intended usage: COMMON

Restrictions on usage: NONE

Author: Sean Turner

Change Controller: S/MIME working group delegated from the IESG

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 [MMA].

- The Diffie-Hellman "small-subgroup" attacks described in RFC
2785 [DHSUB].

- The attacks against hash algorithms described in RFC 4270
[HASH-ATTACK].

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 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.

The choice of 2048 bits as the 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 [STRENGTH].
Of course, there are environments, such as financial and medical
system,
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, 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 which that would result in excessive
cryptographic processing, for example example, keys larger than those
mandated in this specification, which could swamp the processing
element. Agents which 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.

Using weak cryptography in S/MIME offers little actual security over
sending plaintext. However, other features of S/MIME, such as the
specification of AES and the ability to announce stronger
cryptographic capabilities to parties with whom you communicate,
allow senders to create messages that use strong encryption. Using
weak cryptography is never recommended unless the only alternative is
no cryptography.

RSA and DSA keys of less than 1024 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.

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- strongly
encrypted message by decrypting the weakly-encrypted weakly encrypted version. In
other words, a sender SHOULD NOT send a copy of a message using
weaker cryptography than they would use for the original of the
message.

Modification of the ciphertext can go undetected if authentication is
not also used, which is the case when sending EnvelopedData without
wrapping it in SignedData or enclosing SignedData within it.

If an implementation is concerned about compliance with NIST 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
check checked periodically if the indicator is supposed to
give information on the current status of a message.

7. References

7.1. Reference Conventions

[CMS] refers to [RFC5652].

[ESS] refers to [RFC2634] and [RFC5035].

[MIME] refers to [RFC2045], [RFC2046], [RFC2047], [RFC2049],
[RFC4288], and [RFC4289].

[SMIMEv2] refers to [RFC2311], [RFC2312], [RFC2313], [RFC2314], and
[RFC2315].

[SMIMEv3] refers to [RFC2630], [RFC2631], [RFC2632], [RFC2633],
[RFC2634], and [RFC5035].

[SMIMv3.1] refers to [RFC2634], [RFC3850], [RFC3851], [RFC3852], and
[RFC5035].

7.2. Normative References

[CERT32] Ramsdell, B., B. and S. Turner, "S/MIME "Secure/Multipurpose
Internet Mail Extensions (S/MIME) Version 3.2
Certificate Handling", draft-ietf-smime-3850bis-
10.txt, work-in-progress. RFC 5750, December 2009.

[CHARSETS] Character sets assigned by IANA. See
http://www.iana.org/assignments/character-sets.

[CMS] Housley, R., "Cryptographic Message Syntax (CMS)", RFC
3852, July 2004.

Housley, R., "Cryptographic Message Syntax (CMS)
Multiple Signer Clarification", RFC 4853, April 2007.

[CMSAES] Schaad, J., "Use of the Advanced Encryption Standard
(AES) Encryption Algorithm in Cryptographic Message
Syntax (CMS)", RFC 3565, July 2003.

[CMSALG] Housley, R., "Cryptographic Message Syntax (CMS)
Algorithms", RFC 3370, August 2002.

[CMSCOMPR] Gutmann, P., "Compressed Data Content Type for
Cryptographic Message Syntax (CMS)", RFC 3274, June
2002.

[CMS-SHA2] Turner. Turner, S., "Using SHA2 Algorithms with Cryptographic
Message Syntax", draft-ietf-smime-sha2-11.txt, work in
progress. RFC 5754, December 2009.

[CONTDISP] Troost, R., Dorner, S., and K. Moore, Ed.,
"Communicating Presentation Information in Internet
Messages: The Content-Disposition Header Field", RFC
2183, August 1997.

[ESS] Hoffman, P., "Enhanced Security Services

[FIPS186-2] National Institute of Standards and Technology (NIST),
"Digital Signature Standard (DSS)", FIPS Publication
186-2, January 2000. [With Change Notice 1].

[FIPS186-3] National Institute of Standards and Technology (NIST),
FIPS Publication 186-3: Digital Signature Standard,
June 2009.

[MIME-SECURE] Galvin, J., Murphy, S., Crocker, S., and N. Freed,
"Security Multiparts for MIME: Multipart/Signed and
Multipart/Encrypted", RFC 1847, October 1995.

[MUSTSHOULD] Bradner, S., "Key words for use in RFCs to Indicate
Requirement Levels", BCP 14, RFC 2119, March 1997.

[RANDOM] Eastlake, D., 3rd, Schiller, J., and S. Crocker,
"Randomness Requirements for S/MIME", Security", BCP 106, RFC 2634,
4086, June 1999.

Schaad, J., "ESS Update: Adding CertID Algorithm
Agility", RFC 5035, August 2007.

[FIPS186-2] National Institute of Standards and Technology (NIST),
"Digital Signature Standard (DSS)", FIPS Publication
186-2, January 2000. [With Change Notice 1].

[FIPS186-3] National Institute of Standards and Technology (NIST),
FIPS Publication 186-3: Digital Signature Standard,
(draft) March 2006.

[MIME-SPEC] 2005.

[RFC2045] Freed, N. and N. Borenstein, "Multipurpose Internet
Mail Extensions (MIME) Part One: Format of Internet
Message Bodies", RFC 2045, November 1996.

[RFC2046] Freed, N. and N. Borenstein, "Multipurpose Internet
Mail Extensions (MIME) Part Two: Media Types", RFC
2046, November 1996.

[RFC2047] Moore, K., "MIME (Multipurpose Internet Mail
Extensions) Part Three: Message Header Extensions for
Non-ASCII Text", RFC 2047, November 1996.

[RFC2049] Freed, N., N. and J. Klensin, N. Borenstein, "Multipurpose Internet
Mail Extensions (MIME) Part Four: Registration Procedures",
BCP 13, Five: Conformance Criteria
and Examples", RFC 4289, December 2005. 2049, November 1996.

[RFC2634] Hoffman, P. Ed., "Enhanced Security Services for
S/MIME", RFC 2634, June 1999.

[RFC4288] Freed, N., N. and J. Klensin, "Media Type Specifications
and Registration Procedures", BCP 13, RFC 4288,
December 2005.

[RFC4289] Freed, N. and N. Borenstein, J. Klensin, "Multipurpose Internet Mail
Extensions (MIME) Part Five: Conformance Criteria
and Examples", RFC 2049, November 1996.

[MIME-SECURE] Galvin, J., Murphy, S., Crocker, S., and N. Freed,
"Security Multiparts for MIME: Multipart/Signed and
Multipart/Encrypted", RFC 1847, October 1995.

[MUSTSHOULD] Bradner, S., "Key words for use in RFCs to Indicate
Requirement Levels", BCP 14, RFC 2119, March 1997.

[RANDOM] Eastlake 3rd, D., Crocker, S., and J. Schiller,
"Randomness Requirements for Security", Four: Registration Procedures",
BCP 106, 13, RFC
4086, June 4289, December 2005.

[RSAPSS]

[RFC5035] Schaad, J., "Use of RSASSA-PSS Signature "Enhanced Security Services (ESS) Update:
Adding CertID Algorithm in
Cryptographic Agility", RFC 5035, August
2007.

[RFC5652] Housley, R., "Cryptographic Message Syntax (CMS)", RFC 4056, June
2005.
5652, September 2009.

[RSAOAEP] Housley, R. "Use of the RSAES-OAEP Key Transport
Algorithm in the Cryptographic Message Syntax (CMS)",
RFC 3560, July 2003.

[RSAPSS] Schaad, J., "Use of the RSASSA-PSS Signature Algorithm
in Cryptographic Message Syntax (CMS)", RFC 4056, June
2005.

[SP800-56A] National Institute of Standards and Technology (NIST),
Special Publication 800-56A: Recommendation Pair-Wise
Key Establishment Schemes Using Discrete Logarithm
Cryptography (Revised), March 2007.

[X.680] ITU-T Recommendation X.680 (2002) | ISO/IEC 8824-
1:2002.
8824-1:2002. Information Technology - Abstract Syntax
Notation One (ASN.1): Specification of basic notation.

[X.690] ITU-T Recommendation X.690 (2002) | ISO/IEC 8825-
1:2002.
8825-1:2002. Information Technology - ASN.1 encoding
rules: Specification of Basic Encoding Rules (BER),
Canonical Encoding Rules (CER) and Distinguished
Encoding Rules (DER).

7.2.

7.3. Informative References

[DHSUB] Zuccherato, R., "Methods for Avoiding the "Small-
Subgroup" Attacks on the Diffie-Hellman Key Agreement
Method for S/MIME", RFC 2785, March 2000.

[HASH-ATTACK] Hoffman, P., P. and B. Schneier, B., "Attacks on Cryptographic
Hashes in Internet Protocols", RFC 4270, November 2005.

[MMA] Rescorla, E., "Preventing the Million Message Attack on
Cryptographic Message Syntax", RFC 3218, January 2002.

[PKCS-7] Kaliski, B., "PKCS #7: Cryptographic Message Syntax
Version 1.5", RFC 2315, March 1998.

[SMIMEv2]

[RFC2311] Dusse, S., Hoffman, P., Ramsdell, B., Lundblade, L.,
and L. Repka, "S/MIME Version 2 Message Specification",
RFC 2311, March 1998.

[RFC2312] Dusse, S., Hoffman, P., Ramsdell, B., and J. Weinstein,
"S/MIME Version 2 Certificate Handling", RFC 2312,
March 1998.

[RFC2313] Kaliski, B., "PKCS #1: RSA Encryption Version 1.5", RFC
2313, March 1998.

[RFC2314] Kaliski, B., "PKCS #10: Certificate Certification Request Syntax
Version 1.5", RFC 2314, March 1998.

[RFC2315] Kaliski, B., "PKCS #7: Certificate Certification Message Syntax
Version 1.5", RFC 2315, March 1998.

[SMIMEv3]

[RFC2630] Housley, R., "Cryptographic Message Syntax", RFC 2630,
June 1999.

[RFC2631] Rescorla, E., "Diffie-Hellman Key Agreement Method",
RFC 2631, June 1999.

[RFC2632] Ramsdell, B., Ed., "S/MIME Version 3 Certificate
Handling", RFC 2632, June 1999.

Ramsdell, B., "S/MIME Version 3 Message
Specification", RFC 2633, June 1999.

Hoffman, P., "Enhanced Security Services for S/MIME",
RFC 2634, June 1999.

Schaad, J., "ESS Update: Adding CertID Algorithm
Agility", RFC 5035, August 2007.

[SMIMEv3.1] Housley, R., "Cryptographic Message Syntax", RFC 3852,
July 2004.

Housley, R., "Cryptographic

[RFC2633] Ramsdell, B., Ed., "S/MIME Version 3 Message Syntax (CMS)
Multiple Signer Clarification",
Specification", RFC 4853, April 2007. 2633, June 1999.

[RFC3850] Ramsdell, B., "S/MIME Ed., "Secure/Multipurpose Internet Mail
Extensions (S/MIME) Version 3.1 Certificate Handling",
RFC 3850, July 2004.

[RFC3851] Ramsdell, B., "S/MIME Ed., "Secure/Multipurpose Internet Mail
Extensions (S/MIME) Version 3.1 Message Specification",
RFC 3851, July 2004.

Hoffman, P., "Enhanced Security Services for S/MIME",
RFC 2634, June 1999.

Schaad, J., "ESS Update: Adding CertID Algorithm
Agility",

[RFC3852] Housley, R., "Cryptographic Message Syntax (CMS)", RFC 5035, August 2007.
3852, July 2004.

[SP800-57] National Institute of Standards and Technology (NIST),
Special Publication 800-57: Recommendation for Key
Management, August 2005.

[STRENGTH] Orman, H., and P. Hoffman, "Determining Strengths For
Public Keys Used For Exchanging Symmetric Keys", BCP
86, RFC 3766, April 2004.

Appendix A. ASN.1 Module

NOTE:

Note: The ASN.1 module contained herein is unchanged from RFC 3851
[SMIMEv3.1] with the exception of a change to the prefersBinaryInside
ASN.1 comment. 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

--
-- Copyright (c) 2009 IETF Trust and the persons identified as
-- authors of the code. All rights reserved.
--
-- Redistribution and use in source and binary forms, with or
-- without modification, are permitted provided that the following
-- conditions are met:
--
-- - Redistributions of source code must retain the above copyright
-- notice, this list of conditions and the following disclaimer.
--
-- - Redistributions in binary form must reproduce the above
-- copyright notice, this list of conditions and the following
-- disclaimer in the documentation and/or other materials provided
-- with the distribution.
--
-- - Neither the name of Internet Society, IETF or IETF Trust, nor
-- the names of specific contributors, may be used to endorse or
-- promote products derived from this software without specific
-- prior written permission.
--
--
--
-- THIS SOFTWARE IS PROVIDED BY THE COPYRIGHT HOLDERS AND
-- CONTRIBUTORS 'AS IS' AND ANY EXPRESS OR IMPLIED WARRANTIES,
-- INCLUDING, BUT NOT LIMITED TO, THE IMPLIED WARRANTIES OF
-- MERCHANTABILITY AND FITNESS FOR A PARTICULAR PURPOSE ARE
-- DISCLAIMED. IN NO EVENT SHALL THE COPYRIGHT OWNER OR
-- CONTRIBUTORS BE LIABLE FOR ANY DIRECT, INDIRECT, INCIDENTAL,
-- SPECIAL, EXEMPLARY, OR CONSEQUENTIAL DAMAGES (INCLUDING, BUT NOT
-- LIMITED TO, PROCUREMENT OF SUBSTITUTE GOODS OR SERVICES; LOSS
-- OF USE, DATA, OR PROFITS; OR BUSINESS INTERRUPTION) HOWEVER
-- CAUSED AND ON ANY THEORY OF LIABILITY, WHETHER IN CONTRACT,
-- STRICT LIABILITY, OR TORT (INCLUDING NEGLIGENCE OR OTHERWISE)
-- ARISING IN ANY WAY OUT OF THE USE OF THIS SOFTWARE, EVEN IF
-- ADVISED OF THE POSSIBILITY OF SUCH DAMAGE.
--
-- This version of the ASN.1 module is part of RFC XXXX;
-- see the RFC itself for full legal notices.
--

//RFC EDITOR NOTE: Replace XXXX with this RFC's #.

-- 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.

id-aa-encrypKeyPref OBJECT IDENTIFIER ::= {id-aa 11}
SMIMEEncryptionKeyPreference ::= CHOICE {
issuerAndSerialNumber [0] IssuerAndSerialNumber,
receipentKeyId [1] RecipientKeyIdentifier,
subjectAltKeyIdentifier [2] SubjectKeyIdentifier
}

-- receipentKeyId is spelt incorrectly, but kept for historical
-- reasons.

id-smime OBJECT IDENTIFIER ::= { iso(1) member-body(2) us(840)
rsadsi(113549) pkcs(1) pkcs9(9) 16 }

id-cap OBJECT IDENTIFIER ::= { id-smime 11 }

-- The preferBinaryInside 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 list OIDs to be used with S/MIME V3

-- Signature Algorithms Not Found in [CMSALG], [CMS-SHA2], [RSAPSS],
-- and [RSAOAEP]

--
-- 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

Appendix B. Moving S/MIME v2 Message Specification to Historic Status

The S/MIME v3 [SMIMEv3], v3.1 [SMIMEv3.1], and v3.2 (this document)
are backwards 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,
it is recommended that RFC 2311 [SMIMEv2] be moved to Historic
status.

Appendix C. Acknowledgments

Many thanks go out to the other authors of the S/MIME Version version 2
Message Specification RFC: Steve Dusse, Paul Hoffman, Laurence
Lundblade
Lundblade, and Lisa Repka. Without v2, there wouldn't be a v3, v3.1 v3.1,
or v3.2.

A number of the members of the S/MIME Working Group have also worked
very hard and contributed to this document. Any list of people is
doomed to omission, and for that I apologize. In alphabetical order,
the following people stand out in my mind due to the fact that because they made direct
contributions to this document. document:

Tony Capel, Piers Chivers, Dave Crocker, Bill Flanigan, Peter
Gutmann, Alfred Hoenes, Paul Hoffman, Russ Housley, William Ottaway,
John Pawling, and Jim Schaad.

Authors' Addresses

Blake Ramsdell
Brute Squad Labs, Inc.

EMail: blaker@gmail.com

Sean Turner
IECA, Inc.
3057 Nutley Street, Suite 106
Fairfax, VA 22031
USA

EMail: turners@ieca.com