Internet Draft Steve Dusse

draft-dusse-smime-msg-02.txt RSA Data Security

July 5, 1997 Paul Hoffman
Expires January 5, 1998 Internet Mail Consortium
Blake Ramsdell
Deming Internet Security
Laurence Lundblade
Qualcomm
Lisa Repka
Netscape
S/MIME Message Specification
(followed by RFC 2633)
Status of this memo
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1. Introduction
S/MIME (Secure/Multipurpose Internet Mail Extensions) provides a standard 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 privacy and data security (using
encryption).
S/MIME can be used by traditional mail user agents (MUAs) to add cryptographic security services to
mail that is sent, and to interpret cryptographic security services in mail that is received. However,
S/MIME is not restricted to mail; it can be used with any transport mechanism that transports MIME
data, such as HTTP. As such, S/MIME takes advantage of the object-based features of MIME and
allows secure messages to be exchanged in mixed-transport systems.
Further, S/MIME can be used in automated message transfer agents that use cryptographic security
services that do not require any human intervention, such as the signing of software-generated
documents and the encryption of FAX messages sent over the Internet.
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 type of
Internet messages and allows extensions for new content type applications.
This draft defines how to create a MIME body part has been cryptographically enhanced according to
PKCS #7 [PKCS-7]. This draft also defines the application/pkcs7-mime MIME type that can used to
transport those body parts. This draft also defines how to create certification requests that conform to
PKCS #10 [PKCS-10], and the application/pkcs10 MIME type for transporting those request.
This draft also discusses how to use the multipart/signed MIME type defined in [MIME-SECURE] to
transport S/MIME signed messages. This draft also defines the application/pkcs7-signature MIME
type, which is also used to transport S/MIME signed messages. This specification is compatible with
PKCS #7 in that it uses the data types defined by PKCS #7.
In order to create S/MIME messages, an agent has to follow specifications in this draft, as well as some
of the specifications listed in the following pre-standards works:
"PKCS #1: RSA Encryption Standard", [PKCS-1].
"PKCS #7: Cryptographic Message Syntax Standard", [PKCS-7]
"PKCS #10: Certification Request Syntax Standard", [PKCS-10].
Throughout this draft, there are requirements and recommendations made for how receiving agents
handle incoming messages. There are separate requirements and recommendations for how sending
agents create outgoing messages. In general, the best strategy is to "be liberal in what you receive and
conservative in what you send". Most of the requirements are placed on the handling of incoming
messages while the recommendations are mostly on the creation of outgoing messages.
The separation for requirements on receiving agents and sending agents also derives from the likelihood
that there will be S/MIME systems that involve software other than traditional Internet mail clients.
S/MIME can be used with any system that transports MIME data. An automated process that sends an
encrypted message might not be able to receive an encrypted message at all, for example. Thus, the
requirements and recommendations for the two types of agents are listed separately when appropriate.
1.2 Terminology
Throughout this draft, the terms MUST, MUST NOT, SHOULD, and SHOULD NOT are used in
capital letters. This conforms to the definitions in [MUSTSHOULD].
1.3 Definitions
For the purposes of this draft, the following definitions apply.
ASN.1: Abstract Syntax Notation One, as defined in CCITT X.208.
BER: Basic Encoding Rules for ASN.1, as defined in CCITT X.209.
Certificate: A type that binds an entity's distinguished name to a public key with a digital signature.
DER: Distinguished Encoding Rules for ASN.1, as defined in CCITT X.509, Section 8.7.
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 may be sent via a
channel that only transmits 7-bit data.
1.4 Compatibility with Pre-standards S/MIME
Appendix C contains important information about how standards-based S/MIME agents should act in
order to have the greatest interoperability with pre-standards S/MIME.
1.5 Discussion of This Draft
This draft is being discussed on the "ietf-smime" mailing list. To subscribe, send a message to:
[email protected]
with the single word: subscribe
in the body of the message. There is a Web site for the mailing list at <http://www.imc.org/ietf-
smime/>.
2. PKCS #7 Options
The PKCS #7 message format allows for a wide variety of options in content and algorithm support.
This section puts forth a number of support requirements and recommendations in order to achieve a
base level of interoperability among all S/MIME implementations.
2.1 DigestAlgorithmIdentifier
Receiving agents MUST support SHA-1 and MD5.
Sending agents SHOULD use SHA-1.
2.2 DigestEncryptionAlgorithmIdentifier
Receiving agents MUST support rsaEncryption, defined in [PKCS-1]. Receiving agents MUST support
verification of signatures using RSA public key sizes from 512 bits to 1024 bits.
Sending agents MUST support rsaEncryption. Outgoing messages are signed with a user's private key.
The size of the private key is determined during key generation.
2.3 KeyEncryptionAlgorithmIdentifier
Receiving agents MUST support rsaEncryption. Incoming encrypted messages contain symmetric keys
which are to be decrypted with a user's private key. The size of the private key is determined during key
generation.
Sending agents MUST support rsaEncryption. Sending agents MUST support encryption of symmetric
keys with RSA public keys at key sizes from 512 bits to 1024 bits.
2.4 General Syntax
The PKCS #7 defines six distinct content types: "data", "signedData", "envelopedData",
"signedAndEnvelopedData", "digestedData", and "encryptedData". Receiving agents MUST support the
"data", "signedData" and "envelopedData" content types. Sending agents may or may not send out any
of the content types, depending on the services that the agent supports.
2.4.1 Data Content Type
Sending agents MUST use the "data" content type as the content within other content types to indicate
the message content which has had security services applied to it.
2.4.2 Signed-data Content Type
Sending agents MUST use the Signed-data content type to apply a digital signature to a message or, in a
degenerate case where there is no signature information, to convey information pertaining to certificates.
2.4.3 Enveloped-data Content Type
This content type is used to apply privacy protection to a message. A sender needs to have access to a
public key for each intended message recipient to use this service. This content type does not provide
authentication.
2.4.4 Signed-and-enveloped-data Content Type
This content type is used to apply a digital signature as well as privacy protection to a message. A
sender needs to have access to a public key for each intended message recipient to use this service. This
content type should only be used for compatibility with [PEM]. The separate application of signing then
enveloping SHOULD be used in all other cases.
2.5 SignerInfo Type
The SignerInfo type allows the inclusion of unauthenticated and authenticated attributes to be included
along with a signature.
Receiving agents MUST be able to handle and display zero or one instance of each of the signed
attributes described in this section.
Sending agents SHOULD be able to generate one instance of each of the signed attributes described in
this section, and SHOULD include these attributes in each signed and/or encrypted message sent.
2.5.1 Signing-Time Attribute
The signing-time attribute is used to convey the time that a message was signed. Until there are trusted
timestamping services, the time of signing will most likely be created by a message originator and
therefore is only as trustworthy as the originator. The syntax of the signing-time attribute is:
SigningTime ::= UTCTime
2.5.2 SMIMECapabilities Attribute
The SMIMECapabilities attribute includes signature algorithms (such as "md5WithRSAEncryption"),
symmetric algorithms (such as "DES-CBC"), and key encipherment algorithms (such as
"rsaEncryption"). It also includes a non-algorithm capability which is the preference for signedData.
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.
The semantics of the SMIMECapabilites attribute specify a partial list as to what the client announcing
the SMIMECapabilites can support. A client does not have to list every capability it supports, and
probably should 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
logically separated along the lines of their categories (signature algorithms, symmetric algorithms, key
encipherment algorithms, etc.)
The structure of the SMIMECapabilities attribute is to facilitate simple table lookups and binary
comparisons in order to determine matches. For instance, the DER-encoding for the SMIMECapability
for DES EDE3 CBC SHOULD be identically encoded regardless of the
implementation.
In the case of symmetric algorithms, the associated parameters for the OID MUST specify all of the
parameters necessary to differentiate between two instances of the same algorithm. For instance, the
number of rounds and block size for RC5 must be specified in addition to the key length.
There is a list of OIDs (the registered SMIMECapabilities list) that is centrally maintained and is
separate from this draft. Upon moving this draft to standards track, the IANA will maintain the list of
OIDs. Until this draft becomes a draft standard, the list of OIDs is maintained by the Internet Mail
Consortium at <http://www.imc.org/ietf-smime/oids.html>.
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 draft,
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 may be defined in the future. Also, additional
attributes and values for those attributes may be defined in the future. Receiving agents MUST handle a
SMIMECapabilities object that has attributes or values that it does not recognize in a graceful manner.
2.6 ContentEncryptionAlgorithmIdentifier
Receiving agents MUST support decryption and encryption using the RC2 algorithm [RC2] at a key
size of 40 bits, hereinafter called "RC2/40". Receiving agents SHOULD support decryption using DES
EDE3 CBC, hereinafter called "tripleDES".
Sending agents SHOULD support encryption with RC2/40 and tripleDES.
2.6.1 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 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 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 capabilities lists in messages whose signature could not be verified,
SHOULD 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 such as RC2/40. The decision to
use or not use weak encryption overrides any other decision in this section about which encryption
algorithm to use.
Sections 2.6.2.1 through 2.6.2.4 describe the decisions a sending agent SHOULD use in deciding which
type of encryption should be applied to a message. These rules are ordered, so the sending agent
SHOULD make its decision in the order given.
2.6.2.1 Rule 1: Known Capabilities
If the sending agent has received a set of capabilities from the recipient for the message the agent is
about to encrypt, then the sending agent SHOULD use that information by selecting the first capability
in the list (that is, the capability most preferred by the intended recipient) for which sending agent knows
how to encrypt. The sending agent SHOULD use one of the capabilities in the list if the agent
reasonably expects the recipient to be able to decrypt the message.
2.6.2.2 Rule 2: Unknown Capabilities, Known Use of Encryption
If:
- the sending agent has no knowledge of the encryption capabilities of the recipient,
- and the sending agent has received at least one message from the recipient,
- and the last encrypted message received from the recipient had a trusted signature on it, then the
outgoing message SHOULD use the same encryption algorithm as was used on the last signed message
received from the recipient.
2.6.2.3 Rule 3: Unknown Capabilities, Risk of Failed Decryption
If:
- the sending agent has no knowledge of the encryption capabilities of the recipient,
- and the sending agent is willing to risk that the recipient may not be able to decrypt the message, then
the sending agent SHOULD use tripleDES.
2.6.2.4 Rule 4: Unknown Capabilities, No Risk of Failed Decryption
If:
- the sending agent has no knowledge of the encryption capabilities of the recipient,
- and the sending agent is not willing to risk that the recipient may not be able to decrypt the message,
then the sending agent MUST use RC2/40.
2.6.3 Choosing Weak Encryption
Like all algorithms that use 40 bit keys, RC2/40 is considered by many to be weak encryption. A
sending agent that is controlled by a human SHOULD allow a human sender to determine the risks of
sending data using RC2/40 or a similarly weak encryption algorithm before sending the data, and
possibly allow the human to use a stronger encryption method such as tripleDES.
3. Creating S/MIME Messages
This section describes the S/MIME message formats and how they are created. S/MIME messages are a
combination of MIME bodies and PKCS objects. Several MIME types as well as several PKCS objects
are used. The data to be secured is always a canonical MIME entity. The MIME entity and other data,
such as certificates and algorithm identifiers, are given to PKCS processing facilities which produces a
PKCS object. The PKCS object is then finally wrapped in MIME.
S/MIME provides one format for enveloped-only data, several formats for signed-only data, and several
formats for signed and enveloped data. Several formats are required to accommodate several
environments, in particular for signed messages. The criteria for choosing among these formats are also
described.
The reader of this section is expected to understand MIME as described in [MIME-SPEC], [MIME-
SECURE] and [APP-MIME].
3.1 Preparing the MIME Entity for Signing or Enveloping
S/MIME is used to secure MIME entities. A MIME entity may be a sub-part, sub-parts of a message,
or the whole message with all its sub-parts. A MIME entity that is the whole message includes only the
MIME headers and MIME body, and does not include the RFC-822 headers. Note that S/MIME can
also be used to secure MIME entities used in applications other than Internet mail.
The MIME entity that is secured and described in this section can be thought of as the "inside" MIME
entity. That is, it is the "innermost" object in what is possibly a larger MIME message. Processing
"outside" MIME entities into PKCS-7 objects is described in Section 3.2, 3.4 and elsewhere.
The procedure for preparing a MIME entity is given in [MIME-SPEC]. The same procedure is used
here with some additional restrictions when signing. Description of the procedures from [MIME-SPEC]
are repeated here, but the reader should refer to that document for the exact procedure. This section also
describes additional requirements.
A single procedure is used for creating MIME entities that are to be signed, enveloped, or both signed
and enveloped. Some additional steps are recommended to defend against known corruptions that can
occur during mail transport that are of particular importance for clear-signing using the multipart/signed
format. It is recommended that these additional steps be performed on enveloped messages, or signed
and enveloped messages in order that the message can be forwarded to any environment without
modification.
These steps are descriptive rather than prescriptive. The implementor is free to use any procedure as
long as the result is the same.
Step 1. The MIME entity is prepared according to the local conventions
Step 2. The leaf parts of the MIME entity are converted to canonical form
Step 3. Appropriate transfer encoding is applied to the leaves of the MIME entity
When an S/MIME message is received, the security services on the message are removed, and the result
is the MIME entity. That MIME entity is typically passed to a MIME-capable user agent where, it is
further decoded and presented to the user or receiving application.
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 as well as signing.
The exact details of canonicalization depend on the actual MIME type and subtype of an entity, and are
not described here. Instead, the standard for the particular MIME type should be consulted. For
example, canonicalization of type text/plain is different from canonicalization of audio/basic. Other than
text types, most types have only one representation regardless of computing platform or environment
which can be considered their canonical representation. In general, canonicalization will be performed
by the sending agent rather than the S/MIME implementation.
The most common and important canonicalization is for text, which is often represented differently in
different environments. MIME entities of major type "text" must have both their line endings and
character set canonicalized. The line ending must be the pair of characters <CR><LF>, and the
character set should be registered character set. The details of the canonicalization are specified in
[MIME-SPEC].
3.1.2 Transfer Encoding
When generating any of the secured MIME entities below, except the signing using the multipart/signed
format, no transfer encoding at all is required. S/MIME implementations MUST be able to deal with
binary MIME objects. If no Content-Transfer-Encoding header is present, the transfer encoding should
be considered binary.
S/MIME implementations SHOULD however use transfer encoding described in section 3.1.3 for all
MIME entities they secure. The reason for securing only 7-bit MIME entities, even for enveloped data
that are not exposed to the transport, is that it allows the MIME entity to be handled in any environment
without changing it. For example, a trusted gateway might remove the envelope, but not the signature,
of a message, and then forward the signed message on to the 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.
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 transport path is 8-
bit clear. If a mail message with 8-bit data were to encounter a message transfer agent that can not
transmit 8-bit or binary data, the agent has three options, none of which are acceptable for a clear-
signed message.
The agent could change the transfer encoding; this would invalidate the signature.
The agent could transmit the data anyway, which would most likely result in the 8th bit being
corrupted; this too would invalidate the signature
The agent could return the message to the sender.
[MIME-SECURE] prohibits an agent from changing the transfer encoding of the first part of a
multipart/signed message. If a compliant agent that can not transmit 8-bit or binary data encounters a
multipart/signed message with 8-bit or binary data in the first part, it would have to return the message
to the sender as undeliverable.
3.1.4 Sample Canonical MIME Entity
This shows a multipart/signed message with full transfer encoding. This message contains a text part
and an attachment. The sample message text includes characters that are not US-ASCII and thus must
be transfer encoded. Though not shown here, the end of each line is <CR><LF>. The line ending of the
MIME headers, the text, and transfer encoded parts, all must be <CR><LF>.
Content-Type: multipart/mixed; boundary=bar
--bar
Content-Type: text/plain; charset=iso-8859-1
Content-Transfer-Encoding: quoted-printable
Aloha Michael!
How do you like the new S/MIME standard?
I agree. It's generally a good idea to encode lines that begin with
From=20because some mail transport agents will insert a greater-
than (>) sign, thus invalidating the signature.
Also, in some cases it might be desirable to encode any =20
trailing whitespace that occurs on lines in order to ensure =20
that the message signature is not invalidated when passing =20
a gateway that modifies such whitespace (like BITNET). =20
--bar
Content-Type: application/wally-wiggle
iQCVAwUBMJrRF2N9oWBghPDJAQE9UQQAtl7LuRVndBjrk4EqYBIb3h5QXIX/LC//
jJV5bNvkZIGPIcEmI5iFd9boEgvpirHtIREEqLQRkYNoBActFBZmh9GC3C041WGq
uMbrbxc+nIs1TIKlA08rVi9ig/2Yh7LFrK5Ein57U/W72vgSxLhe/zhdfolT9Brn
HOxEa44b+EI=
=ndaj
--bar--
3.2 The application/pkcs7-mime Type
The application/pkcs7-mime type is used to carry a PKCS-7 objects of several types including
envelopedData and signedData. The details of constructing these entities is described in subsequent
sections. This section describes the general characteristics of the application/pkcs7-mime type.
This MIME type always carries a single PKCS-7 object. The PKCS-7 object must always be BER
encoding of the ASN.1 syntax describing the object. The contentInfo field of the carried PKCS-7
object always contains a MIME entity that is prepared as described in section 3.1. The contentInfo
field must never be empty.
Since PKCS-7 objects are binary data, in most cases base-64 transfer encoding is appropriate, in
particular when used with SMTP transport. The transfer encoding used depends on the transport
through which object is to be sent, and is not a characteristic of the MIME type.
Note that this discussion refers to the transfer encoding of the PKCS-7 object or "outside" MIME entity.
It is completely distinct from, and unrelated to, the transfer encoding of the MIME entity secured by the
PKCS-7 object, the "inside" object, which is described in section 3.1.
[Note: the following has been added to the spec, and is not in earlier versions. It should not cause any
incompatibilities with pre-standards S/MIME implementations, and should help receiving agents.]
Because there are several types of application/pkcs7-mime objects, a sending agent SHOULD do as
much as possible to help a receiving agent know about the contents of the object without forcing the
receiving agent to decode the ASN.1 for the object. The MIME headers of all application/pkcs7-mime
objects SHOULD include the optional "smime-type" parameter, as described in the following sections.
3.2.1 The name and filename Parameters
For the application/pkcs7-mime, sending agents SHOULD emit the optional "name" parameter to the
Content-Type field for compatibility with older systems. Sending agents SHOULD also emit the
optional Content-Disposition field 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:
S/MIME Type File Extension
application/pkcs7-mime .p7m
(signedData, envelopedData)
application/pkcs7-mime .p7c
(degenerate signedData
"certs-only" message)
application/pkcs7-signature .p7s
application/pkcs10 .p10
In addition, the file name SHOULD be limited to eight characters followed by a three letter extension.
The eight character filename base can be any distinct name; the use of the filename "smime" SHOULD
be used to indicate that the MIME entity is associated with S/MIME.
Including a file name serves two purposes. It facilitates easier use of S/MIME objects as files on disk. It
also can convey type information across gateways. When a MIME entity of type application/pkcs7-
mime (for example) arrives at a gateway that has no special knowledge of S/MIME, it will default the
entity's MIME type to application/octet-stream and treat it as a generic attachment, thus losing the type
information. However, the suggested filename for an attachment is often carried across a gateway. This
often allows the receiving systems to determine the appropriate application to hand the attachment off
to, in this case a stand-alone S/MIME processing application. Note that this mechanism is provided as a
convenience for implementations in certain environments. A proper S/MIME implementation MUST
use the MIME types and should not rely on the file extensions.
3.3 Creating an Enveloped-only Message
This section describes the format for enveloping a MIME entity without signing it.
Step 1. The MIME entity to be enveloped is prepared according to section 3.1.
Step 2. The MIME entity and other required data is processed into a PKCS-7 object of type
envelopedData.
Step 3. The PKCS-7 object is inserted into an application/pkcs7-mime MIME entity.
The smime-type parameter for enveloped-only messages is "enveloped-data". The file type 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 Message
There are two formats for signed messages defined for S/MIME. The criteria for choosing among them
are given in section 3.8.
3.4.1 Signing Using application/pkcs7-mime and SignedData
This signing format uses the application/pkcs7-mime MIME type. The steps to create this format are:
Step 1. The MIME entity is prepared according to section 3.1
Step 2. The MIME entity and other required data is processed into a PKCS-7 object of type
signedData
Step 3. The PKCS-7 object is inserted into an application/pkcs7-mime MIME entity
The smime-type parameter for messages using application/pkcs7-mime and SignedData is "signed-
data". The file type 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
3.4.2 Signing Using the Multipart/signed Format
This format is a clear-signing format. Recipients without any S/MIME or PKCS processing facilities
are able to view the message. It makes use of the multipart/signed MIME type described in [MIME-
SECURE]. The multipart/signed MIME type has two parts. The first part contains the MIME entity
that is to be signed; the second part contains the signature, which is a PKCS-7 detached signature.
3.4.2.1 The application/pkcs7-signature MIME type
This MIME type always contains a single PKCS-7 object of type signedData. The contentInfo
field of the PKCS-7 object must be empty. The signerInfos field contains the signatures for the
MIME entity. The details of the registered type are given in Appendix XX.
The file type for signed-only messages using application/pkcs7-signature is ".p7s".
3.4.2.2 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 PKCS-7 processing in order to obtain an object of type
signedData with an empty contentInfo field.
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 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 parameters: the protocol parameter (required), and the
micalg parameter (optional).
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 optional 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 used in the calculation of
the Message Integrity Check.
3.4.2.3 Sample mulipart/signed message
Content-Type: multipart/signed;
protocol="application/pkcs7-signature";
micalg=rsa-md5; 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--
3.4.2.4 Encapsulation Using application/mime
In some cases, multipart/signed entities are automatically decomposed in such a way as to make
computing the hash of the first part, the signed part, impossible; in such a situation, the signature
becomes unverifiable. In order to prevent such decomposition until the MIME entity can be processed in
a proper S/MIME environment, a multipart/signed entity may be encapsulated in an application/mime
entity.
All S/MIME implementations SHOULD be able to generate and receive application/mime
encapsulations of multipart/signed entities which have their signature of type application/pkcs7-mime.
In particular, on receipt of a MIME entity of type application/mime with the type parameter
"multipart/signed" and the protocol parameter "application/pkcs7-mime", a receiving agent SHOULD
be able to process the entity correctly. This is required even if the local environment has facilities for
processing application/mime because the application/mime standard requires that the encapsulated
entity only be processed on request of the user, or if processing software can process the entity
completely and correctly. In this case, an S/MIME facility can always process the entity completely and
SHOULD do so.
The steps to create an application/mime encapsulation of a multipart/signed entity are:
Step 1. Prepare a multipart/signed message as described in section 3.4.2.2
Step 2. Insert the multipart/signed entity into an application/mime according to [APP-MIME]. This
requires that the parameters of the multipart/signed entity be included as parameters on the
application/mime entity.
In addition, the application/mime entity SHOULD have a name parameter giving a file name ending
with ".aps". It SHOULD also have a content-disposition parameter with the same filename. The ".aps"
extension SHOULD be used exclusively for application/mime encapsulated multipart/signed entities
containing a signature of type application/pkcs7-signature. This is necessary so that the receiving agent
can correctly dispatch to software that verifies S/MIME signatures in environments where the MIME
type and parameters have been lost or can't be used for such dispatch. Basically, the file extension
becomes the sole carrier of type information.
A sample application/mime encapsulation of a signed message might be:
Content-type: application/mime; content-type="multipart/signed";
protocol="application/pkcs7-signature";
micalg=rsa-md5; name=smime.aps
Content-disposition: attachment; filename=smime.aps
Content-Type: multipart/signed;
protocol="application/pkcs7-signature";
micalg=rsa-md5; boundary=boundary42
--boundary42
Content-Type: text/plain
This is a very short clear-signed message. However, at least you
can read it!
--boundary42
Content-Type: application/pkcs7-signature
Content-Transfer-Encoding: base64
ghyHhHUujhJhjH77n8HHGTrfvbnj756tbB9HG4VQpfyF467GhIGfHfYT6
4VQpfyF467GhIGfHfYT6jH77n8HHGghyHhHUujhJh756tbB9HGTrfvbnj
n8HHGTrfvhJhjH776tbB9HG4VQbnj7567GhIGfHfYT6ghyHhHUujpfyF4
7GhIGfHfYT64VQbnj756
--boundary42--
3.4.2.5 Encapsulation in an Non-MIME Environment
While this standard primarily addresses the Internet, it is useful to compose and receive S/MIME
secured messages in non-MIME environments. This is particularly the case when it is desired that
security be implemented end-to-end. Other discussion here addresses the receipt of S/MIME messages
in non-MIME environments. Here the composition of multipart/signed entities is addressed.
When a message is to be sent in such an environment, the multipart/signed entity is created as described
above. That entity is then treated as an opaque stream of bits and added to the message as an
attachment. It must have a file name that ends with ".aps", as this is the sole mechanism for recognizing
it as an S/MIME message by the receiving agent.
When this message arrives in a MIME environment, it is likely to have a MIME type of
application/octet-stream, with MIME parameters giving the filename for the attachment. If the
intervening gateway has carried the file type, it will end in ".aps" and be recognized as an S/MIME
message.
3.5 Signing and Encrypting
To achieve signing and enveloping, any of the signed-only and encrypted-only formats may be nested.
This is allowed because the above formats are all MIME entities, and because they all secure MIME
entities. In addition, PKCS-7 provides a data type for enveloped and signed data, and its use is
described here.
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 either sign a message first, or to envelope the message first. It is up to the implementor
and the user to chose. 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 may be useful in an environment were automatic signature verification is
desired, as no private key material is required to verify a signature.
3.6 Creating a Certificates-only Message
The certificates only message or MIME entity is used to transport certificates, such as in response to a
registration request. This format can also be used to convey CRLs.
Step 1. The certificates are made available to the PKCS-7 generating process which creates a PKCS
object of type signedData. The contentInfo and signerInfos fields must be empty.
Step 2. The PKCS-7 signedData object is enclosed in an application/pkcs7-mime MIME entity
The smime-type parameter for a certs-only messages is "certs-only". The file type for this type of
message is ".p7c".
3.7 Creating a Registration Request
A typical application which allows a user to generate cryptographic information has to submit that
information to a certification authority, who transforms it into a certificate. PKCS #10 describes a
syntax for certification requests. The application/pkcs10 body type MUST be used to transfer a PKCS
#10 certification request.
The details of certification requests and the process of obtaining a certificate are beyond the scope of
this draft. Instead, only the format of data used in application/pkcs10 is defined.
3.7.1 Format of the Application/pkcs10 Body
PKCS #10 defines the ASN.1 type CertificationRequest for use in submitting a certification
request. Therefore, when the MIME content type application/pkcs10 is used, the body MUST be a
CertificationRequest, encoded using the Basic Encoding Rules (BER).
Although BER is specified, instead of the more restrictive DER, a typical application will use DER
since the CertificationRequest 's CertificationRequestInfohas to be DER-encoded
in order to be signed. A robust application SHOULD output DER, but allow BER or DER on input.
Data produced by BER or DER is 8-bit, but many transports are limited to 7-bit data. Therefore, a
suitable 7-bit Content-Transfer-Encoding SHOULD be applied. The base64 Content-Transfer-Encoding
SHOULD be used with application/pkcs10, although any 7-bit transfer encoding may work.
3.7.2 Sending and Receiving an application/pkcs10 Body Part
For sending a certificate-signing request, the application/pkcs10 message format MUST be used to
convey a PKCS #10 certificate-signing request. Note that for sending a certificates and CRLs messages
without any signed content, the application/pkcs7-mime message format MUST be used to convey a
degenerate PKCS #7 signedData "certs-only" message.
To send an application/pkcs10 body, the application generates the cryptographic information for the
user. The details of the cryptographic information are beyond the scope of this draft.
Step 1. The cryptographic information is placed within a PKCS #10 CertificationRequest.
Step 2. The CertificationRequest is encoded according to BER or DER (typically, DER).
Step 3. As a typical step, the DER-encoded CertificationRequest is also base64 encoded so
that it is 7-bit data suitable for transfer in SMTP. This then becomes the body of an application/pkcs10
body part.
The result might look like this:
Content-Type: application/pkcs10; name=smime.p10
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename=smime.p10
rfvbnj756tbBghyHhHUujhJhjH77n8HHGT9HG4VQpfyF467GhIGfHfYT6
7n8HHGghyHhHUujhJh4VQpfyF467GhIGfHfYGTrfvbnjT6jH7756tbB9H
f8HHGTrfvhJhjH776tbB9HG4VQbnj7567GhIGfHfYT6ghyHhHUujpfyF4
0GhIGfHfQbnj756YT64V
A typical application only needs to send a certification request. It is a certification authority that has to
receive and process the request. The steps for recovering the CertificationRequest from the
message are straightforward but are not presented here. The procedures for processing the certification
request are beyond the scope of this document.
3.8 Choosing a Format for Signed-only Messages
There are no hard-and fast rules when a particular signed-only format should be chosen because it
depends on the capabilities of all the receivers and the relative importance of receivers with S/MIME
facilities being able to verify the signature versus the importance of receivers without S/MIME software
being able to view the message.
Messages signed using the multipart/signed format can always be viewed by the receiver whether they
have S/MIME software or not. They can also be viewed whether they are using a MIME-native user
agent or they have messages translated by a gateway. In this context, "be viewed" means the ability to
process the message essentially as if it were not a signed message, including any other MIME structure
the message might have.
Messages signed using the signedData format cannot be viewed by a recipient unless they have
S/MIME facilities. However, if they have S/MIME facilities, these messages can always be verified if
they were not changed in transit.
3.8.1 Rationale for Multiple Signing Formats
The rationale behind the multiple formats for signing has to do with the MIME subtype defaulting rules
of the application and multipart top-level types, and the behavior of currently deployed gateways and
mail user agents.
Ideally, the multipart/signed format would be the only format used because it provides a truly
backwards compatible way to sign MIME entities. In a pure MIME environment with very capable user
agents, this would be possible. The world, however, is more complex than this.
One problem with the multipart/signed format occurs with gateways to non-MIME environments. In
these environments, the gateway will generally not be S/MIME aware, will not recognize the
multipart/signed type, and will default its treatment to multipart/mixed as is prescribed by the MIME
standard. The real problem occurs when the gateway also applies conversions to the MIME structure of
the original message that is being signed and is contained in the first part of the multipart/signed
structure, such as the gateway converting text and attachments to the local format. Because the
signature is over the MIME structure of the original message, but the original message is now
decomposed and transformed, the signature cannot be verified. Because MIME encoding of a particular
set of body parts can be done in many different ways, there is no way to reconstruct the original MIME
entity over which the signature was computed.
A similar problem occurs when an attempt is made to combine an existing user agent with a stand-alone
S/MIME facility. Typical user agents do not have the ability to make a multipart sub-entity available to
a stand-alone application in the same way they make leaf MIME entities available to "viewer"
applications. This user agent behavior is not required by the MIME standard and thus not widely
implemented. The result is that it is impossible for most user agents to hand off the entire
multipart/signed entity to a stand-alone application.
3.8.2 Solutions to the Problem
To work around these two problems, the application/pkcs7-mime type can be used. When going through
a gateway, it will be defaulted to the MIME type of application/octet-stream and treated as a single
opaque entity. That is, the message will be treated as an attachment of unknown type, converted into the
local representation for an attachment and thus can be made available to an S/MIME facility completely
intact. A similar result is achieved when a user agent similarly treats the application/pkcs7-mime MIME
entity as a simple leaf node of the MIME structure and makes it available to viewer applications.
Another way to work around these problems is to encapsulate the multipart/signed MIME entity in a
MIME entity of type application/mime. The result is similar to that obtained using application/pkcs7-
mime. When the application/mime entity arrives at a gateway that does not recognize it, its type will be
defaulted to application/octet-stream and it will be treated as a single opaque entity. A similar situation
will happen with a receiving client that does not recognize the entity. It will usually be treated as a file
attachment. It can then be made available to the S/MIME facility.
The major difference between the two alternatives (application/pkcs7-mime or multipart/signed wrapped
with application/mime ) is when the S/MIME facility opens the attachment. In the latter case, the
S/MIME agent will find a multipart/signed entity rather than a BER encoded PKCS7-object.
Considering the two representations abstractly, the only difference is syntax.
The application/mime standard is a general mechanism for encapsulating MIME, and in particular
delaying its interpretation until it can be done in the appropriate environment or at the request of the
user. The application/mime specification does not permit a user agent to automatically interpret the
encapsulated MIME unless it can be processed entirely and properly. The parameters to the
application/mime entity give the type of the encapsulated entity so it can be determined whether or not
the entity can be processed before it is expanded.
Application/mime is a general encapsulation mechanism that can be built into a gateway or user agent,
allowing expansion of the encapsulated entity under user control. Because it is a general mechanism, it
is in many cases more likely to be available than an S/MIME facility. Thus, it enables users to expand
or to verify signed messages based on their local facilities and choices. It provides exactly the same
advantages that the application/pkcs7-mime with signedData does. It also has the added benefit of
allowing expansion in non S/MIME environments and expansion under the recipients control in.
3.8.3 Deciding Which Format To Use
The following table gives criteria for selecting the signature message format in order of
preference if the criteria is met:
mulipart/signed
If it is unknown whether or not all the recipients have S/MIME processing facilities and
It is unknown whether or not the have the ability to process the application/mime type and
It is more important that the message be read by all recipients than it be verifiable
application/mime
It is known that all recipients have the ability to process messages of the type application/mime
It does not matter whether or not they have S/MIME facilities
signedData
It is known that all recipients have S/MIME facilities
The sender may determine whether or not a recipient has S/MIME facilities by keeping track of
messages they have received from that person in an address book or other facility. If they have received
S/MIME messages from a particular address, is it safe to conclude that S/MIME messages may be sent
to that address.
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 below.
The file suffix in the table below comes from the "name" parameter in the content-type header, or the
"filename" parameter on the content-disposition header. These parameters that give the file suffix are
not listed below as part of the parameter section.
MIME type: application/pkcs7-mime
parameters: any
file suffix: any
MIME type: mulitpart/signed
parameters: protocol="application/pkcs7-signature"
file suffix: any
MIME type: application/mime
parameters: content-type="multipart/signed";
protocol="application/pkcs7-signature"
file suffix: any
MIME type: application/octet-stream
parameters: any
file suffix: p7m, p7s, aps, p7c, p10
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 draft does not cover how S/MIME agents handle
certificates, only what they do after a certificate has been validated or rejected. S/MIME certification
issues are covered in a different document.
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
An S/MIME agent or some related administrative utility or function MUST be capable of generating
RSA key pairs on behalf of the user. Each key pair MUST be generated from a good source of non-
deterministic random input and protected in a secure fashion.
A user agent SHOULD generate RSA key pairs at a minimum key size of 768 bits and a maximum key
size of 1024 bits. A user agent SHOULD NOT generate RSA key pairs less than 512 bits long. Some
agents created in the United States have chosen to create 512 bit keys in order to get more advantageous
export licenses. However, 512 bit keys are considered by many to be cryptographically insecure.
5. Security
This entire draft discusses security. Security issues not covered in other parts of the draft include:
40-bit encryption is considered weak by most cryptographers. Using weak cryptography in S/MIME
offers little actual security over sending plaintext. However, other features of S/MIME, such as the
specification of tripleDES and the ability to announce stronger cryptographic capabilities to parties with
whom you communicate, allow senders to create messages that use strong encryption. Using weak
cryptography is never recommended unless the only alternative is no cryptography. When feasible,
sending and receiving agents should inform senders and recipients the relative cryptographic strength of
messages.
It is impossible for most software or people to estimate the value of a message. Further, it is impossible
for most software or people to estimate the actual cost of decrypting a message that is encrypted with a
key of a particular size. Further, it is quite difficult to determine the cost of a failed decryption if a
recipient cannot decode a message. Thus, choosing between different key sizes (or choosing whether to
just use plaintext) is also impossible. However, decisions based on these criteria are made all the time,
and therefore this draft gives a framework for using those estimates in choosing algorithms.
Appendix A - Object Identifiers & Syntax
The syntax for SMIMECapability is:
SMIMECapability ::= SEQUENCE {
capabilityID OBJECT IDENTIFIER,
parameters OPTIONAL ANY DEFINED BY capabilityID }
SMIMECapabilities ::= SEQUENCE OF SMIMECapability
A.1 Content Encryption Algorithms
RC2-CBC OBJECT IDENTIFIER ::=
{iso(1) member-body(2) US(840) rsadsi(113549) encryptionAlgorithm(3) 2}
For the effective-key-bits (key size) other than 32 and less than 256, the RC2-CBC algorithm
parameters are encoded as:
RC2-CBC parameter ::= SEQUENCE {
rc2ParameterVersion INTEGER,
iv OCTET STRING (8)}
For the effective-key-bits of 40, 64, and 128, the rc2ParameterVersion values are 160, 120, 58
respectively.
DES-EDE3-CBC OBJECT IDENTIFIER ::=
{iso(1) member-body(2) US(840) rsadsi(113549) encryptionAlgorithm(3) 7}
For DES-CBC and DES-EDE3-CBC, the parameter should be encoded as:
CBCParameter :: IV
where IV ::= OCTET STRING -- 8 octets.
A.2 Digest Algorithms
md5 OBJECT IDENTIFIER ::=
{iso(1) member-body(2) US(840) rsadsi(113549) digestAlgorithm(2) 5}
sha-1 OBJECT IDENTIFIER ::=
{iso(1) identified-organization(3) oiw(14) secsig(3) algorithm(2) 26}
A.3 Asymmetric Encryption Algorithms
rsaEncryption OBJECT IDENTIFIER ::=
{iso(1) member-body(2) US(840) rsadsi(113549) pkcs(1) pkcs-1(1) 1}
rsa OBJECT IDENTIFIER ::=
{joint-iso-ccitt(2) ds(5) algorithm(8) encryptionAlgorithm(1) 1}
A.3 Signature Algorithms
md2WithRSAEncryption OBJECT IDENTIFIER ::=
{iso(1) member-body(2) US(840) rsadsi(113549) pkcs(1) pkcs-1(1) 2}
md5WithRSAEncryption OBJECT IDENTIFIER ::=
{iso(1) member-body(2) US(840) rsadsi(113549) pkcs(1) pkcs-1(1) 4}
sha-1WithRSAEncryption OBJECT IDENTIFIER ::=
{iso(1) member-body(2) US(840) rsadsi(113549) pkcs(1) pkcs-1(1) 5}
A.4 Signed Attributes
signingTime OBJECT IDENTIFIER ::=
{iso(1) member-body(2) US(840) rsadsi(113549) pkcs(1) pkcs-9(9) 5}
B. References
[MIME-APP] "Wrapping MIME Objects: Application/MIME", Internet Draft draft-crocker-wrap-
01.txt.
[MIME-SPEC] The primary definition of MIME. "MIME Part 1: Format of Internet Message Bodies",
RFC 2045; "MIME Part 2: Media Types", RFC 2046; "MIME Part 3: Message Header Extensions for
Non-ASCII Text", RFC 2047; "MIME Part 4: Registration Procedures", RFC 2048; "MIME Part 5:
Conformance Criteria and Examples", RFC 2049
[MIME-SECURE] "Security Multiparts for MIME: Multipart/Signed and Multipart/Encrypted", RFC
1847
[MUSTSHOULD] "Key words for use in RFCs to Indicate Requirement Levels", RFC 2119
[PEM] "Privacy-Enhanced Mail (PEM) basics", RFC 1421
[PKCS-1], "PKCS #1: RSA Encryption", Internet Draft draft-hoffman-pkcs-rsa-encrypt
[PKCS-7], "PKCS #7: Cryptographic Message Syntax", Internet Draft draft-hoffman-pkcs-crypt-msg
[PKCS-10], "PKCS #10: Certification Request Syntax", Internet Draft draft-hoffman-pkcs-certif-req
[RC2] "Description of the RC2 Encryption Algorithm, Internet Draft draft-rivest-rc2desc
C. Compatibility with Pre-standards S/MIME
S/MIME was originally developed by RSA Data Security, Inc. Many developers implemented S/MIME
agents before the standard was turned over to the IETF. All S/MIME receiving agents SHOULD make
every attempt to interoperate with pre-standards S/MIME sending agents.
C.1 Pre-standards MIME Types
Pre-standard S/MIME agents used the following MIME types:
application/x-pkcs7-mime
application/x-pkcs7-signature
application/x-pkcs10
In each case, the "x-" subtypes correspond to the subtypes described in this document without
the "x-".
C.2 Pre-standards Profiles
Pre-standard S/MIME had two profiles for encryption: "restricted" and "unrestricted". The difference
between these profiles historically came about due to US Government export regulations, as described
at the end of this section. It is expected that in the future, there will be few agents that only use the
restricted profile.
Briefly, the restricted profile required the ability to encrypt and decrypt using RSA's trade-secret RC2
algorithm in CBC mode with 40-bit keys. The unrestricted profile required the ability to encrypt and
decrypt using RSA's trade-secret RC2 algorithm in CBC mode with 40-bit keys, and to encrypt and
decrypt using tripleDES. The restricted profile also had non-manditory suggestions for other algorithms,
but these were not widely implemented.
It is important to note that many current implementations of S/MIME use the restricted profile.
C.2.1 Historical Reasons for the Existence of Two Encryption Profiles
Due to US Government export regulations, an S/MIME agent which supports a strong content
encryption algorithm such as DES would not be freely exportable outside of North America. US
software manufacturers have been compelled to incorporate an exportable or "restricted" content
encryption algorithm in order to create a widely exportable version of their product. S/MIME agents
created in the US and intended for US domestic use (or use under special State Department export
licenses) can utilize stronger, "unrestricted" content encryption. However, in order to achieve
interoperability, such agents need to support whatever exportable algorithm is incorporated in restricted
S/MIME agents.
The RC2 symmetric encryption algorithm has been approved by the US Government for "expedited"
export licensing at certain key sizes. Consequently, support for the RC2 algorithm in CBC mode is
required for baseline interoperability in all S/MIME implementations. Support for other strong
symmetric encryption algorithms such as RC5 CBC, DES CBC and DES EDE3-CBC for content
encryption is strongly encouraged where possible.
D. Revision History
The following changes were made between the -01 and -02 revisions of this draft:
Changed the "FOO" from the previous draft back to RC2 and gave a reference to the Internet Draft
describing it. Added back the OIDs for RC2 in Appendix A.
All of section 3 was completely replaced.
Updated the reference section to point to Internet Drafts for PKCS docs.
Removed the reference to PKCS #9 in 2.5.1 by stating the syntax.
Removed signedAndEnveloped from the draft.
E. Request for New MIME Subtypes
E.1 application/pkcs7-mime
To: [email protected]
Subject: Registration of MIME media type application/pkcs7-mime
MIME media type name: application
MIME subtype name: pkcs7-mime
Required parameters: none
Optional parameters: none
Encoding considerations: Will be binary data, therefore should use
base64 encoding
Security considerations: Described in [PKCS-7]
Interoperability considerations: Designed to carry data formatted
with PKCS-7, as described in [PKCS-7]
Published specification: draft-dusse-smime-msg-xx
Applications which use this media type: Secure Internet mail and
other secure data transports.
Additional information:
File extension(s): .p7m and .p7c
Macintosh File Type Code(s):
Person & email address to contact for further information:
Steve Dusse, [email protected]
Intended usage: COMMON
E.2 application/pkcs7-signature
To: [email protected]
Subject: Registration of MIME media type application/pkcs7-signature
MIME media type name: application
MIME subtype name: pkcs7-signature
Required parameters: none
Optional parameters: none
Encoding considerations: Will be binary data, therefore should use
base64 encoding
Security considerations: Described in [PKCS-7]
Interoperability considerations: Designed to carry digital
signatures with PKCS-7, as described in [PKCS-7]
Published specification: draft-dusse-smime-msg-xx
Applications which use this media type: Secure Internet mail and
other secure data transports.
Additional information:
File extension(s): .p7s
Macintosh File Type Code(s):
Person & email address to contact for further information:
Steve Dusse, [email protected]
Intended usage: COMMON
E.3 application/pkcs10
To: [email protected]
Subject: Registration of MIME media type application/pkcs10
MIME media type name: application
MIME subtype name: pkcs10
Required parameters: none
Optional parameters: none
Encoding considerations: Will be binary data, therefore should use
base64 encoding
Security considerations: Described in [PKCS-10]
Interoperability considerations: Designed to carry digital
certificates formatted with PKCS-10, as described in [PKCS-10]
Published specification: draft-dusse-smime-msg-xx
Applications which use this media type: Secure Internet mail and other
transports where certificates are required.
Additional information:
File extension(s): .p10
Macintosh File Type Code(s):
Person & email address to contact for further information:
Steve Dusse, [email protected]
Intended usage: COMMON
F. Open Issues
Make the micalg parameter required, not optional.
Need reference to allowed values for the micalg parameter in 3.4.2.2.
What to do if sending to multiple people with different known capabilities? What if sending to a group,
some of whom have known capabilities, others with unknown?
Do we need better heuristics for determining the encryption capabilities of a recipient? What about
guessing based on key length?
In section 3.4.2.4, we need to look at whether the SHOULDs should be MUSTs.
References to the encryption and hash algorithms.
Use of the S/MIME trademark.
Need to list text values for the micalg parameter of multipart/signed. RFC 1848 lists only "RSA-MD2"
and "RSA-MD5", not "SHA-1".
What does PEM compatibility mean/entail, and do we care?
Look at the use of PKCS-7 "data" format.
G. Trademarks
RSA Data Security, Inc., owns the US trademark for the name "S/MIME" and for a logo associated
with that name. RSA Data Security, Inc., is considering allowing the use of the name for work done in
the IETF. The name "S/MIME" may or may not be used in future versions of this draft.
H. Acknowledgements
Significant contributions to the content of this draft were made by many people, including:
Jeff Thompson Jeff Weinstein