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Internet Engineering Task Force (IETF)                       B. CampbellRequest for Comments: 8591                             Standard VelocityUpdates:3261,3428,4975                                     R. HousleyCategory: Standards Track                                 Vigil SecurityISSN: 2070-1721                                               April 2019SIP-Based Messaging with S/MIMEAbstract   Mobile messaging applications used with the Session Initiation   Protocol (SIP) commonly use some combination of the SIP MESSAGE   method and the Message Session Relay Protocol (MSRP).  While these   provide mechanisms for hop-by-hop security, neither natively provides   end-to-end protection.  This document offers guidance on how to   provide end-to-end authentication, integrity protection, and   confidentiality using the Secure/Multipurpose Internet Mail   Extensions (S/MIME).  It updates and provides clarifications for RFCs   3261, 3428, and 4975.Status of This Memo   This is an Internet Standards Track document.   This document is a product of the Internet Engineering Task Force   (IETF).  It represents the consensus of the IETF community.  It has   received public review and has been approved for publication by the   Internet Engineering Steering Group (IESG).  Further information on   Internet Standards is available inSection 2 of RFC 7841.   Information about the current status of this document, any errata,   and how to provide feedback on it may be obtained athttps://www.rfc-editor.org/info/rfc8591.Campbell & Housley           Standards Track                    [Page 1]

RFC 8591                S/MIME for SIP Messaging              April 2019Copyright Notice   Copyright (c) 2019 IETF Trust and the persons identified as the   document authors.  All rights reserved.   This document is subject toBCP 78 and the IETF Trust's Legal   Provisions Relating to IETF Documents   (https://trustee.ietf.org/license-info) in effect on the date of   publication of this document.  Please review these documents   carefully, as they describe your rights and restrictions with respect   to this document.  Code Components extracted from this document must   include Simplified BSD License text as described in Section 4.e of   the Trust Legal Provisions and are provided without warranty as   described in the Simplified BSD License.Campbell & Housley           Standards Track                    [Page 2]

RFC 8591                S/MIME for SIP Messaging              April 2019Table of Contents1.  Introduction  . . . . . . . . . . . . . . . . . . . . . . . .42.  Terminology . . . . . . . . . . . . . . . . . . . . . . . . .43.  Problem Statement and Scope . . . . . . . . . . . . . . . . .54.  Applicability of S/MIME . . . . . . . . . . . . . . . . . . .64.1.  Signed Messages . . . . . . . . . . . . . . . . . . . . .64.2.  Encrypted Messages  . . . . . . . . . . . . . . . . . . .74.3.  Signed and Encrypted Messages . . . . . . . . . . . . . .94.4.  Certificate Handling  . . . . . . . . . . . . . . . . . .94.4.1.  Subject Alternative Name  . . . . . . . . . . . . . .94.4.2.  Certificate Validation  . . . . . . . . . . . . . . .95.  Transfer Encoding . . . . . . . . . . . . . . . . . . . . . .96.  User Agent Capabilities . . . . . . . . . . . . . . . . . . .107.  Using S/MIME with the SIP MESSAGE Method  . . . . . . . . . .117.1.  Size Limit  . . . . . . . . . . . . . . . . . . . . . . .117.2.  SIP User Agent Capabilities . . . . . . . . . . . . . . .117.3.  Failure Cases . . . . . . . . . . . . . . . . . . . . . .128.  Using S/MIME with MSRP  . . . . . . . . . . . . . . . . . . .128.1.  Chunking  . . . . . . . . . . . . . . . . . . . . . . . .128.2.  Streamed Data . . . . . . . . . . . . . . . . . . . . . .138.3.  Indicating Support for S/MIME . . . . . . . . . . . . . .148.4.  MSRP URIs . . . . . . . . . . . . . . . . . . . . . . . .148.5.  Failure Cases . . . . . . . . . . . . . . . . . . . . . .159.  S/MIME Interaction with Other SIP Messaging Features  . . . .159.1.  Common Profile for Instant Messaging  . . . . . . . . . .159.2.  Instant Message Disposition Notifications . . . . . . . .1610. Examples  . . . . . . . . . . . . . . . . . . . . . . . . . .17     10.1.  Signed Message in SIP including the Sender's Certificate  1710.2.  Signed Message in SIP with No Certificate  . . . . . . .1910.3.  MSRP Signed and Encrypted Message in a Single Chunk  . .20     10.4.  MSRP Signed and Encrypted Message Sent in Multiple            Chunks . . . . . . . . . . . . . . . . . . . . . . . . .2111. IANA Considerations . . . . . . . . . . . . . . . . . . . . .2312. Security Considerations . . . . . . . . . . . . . . . . . . .2313. References  . . . . . . . . . . . . . . . . . . . . . . . . .2513.1.  Normative References . . . . . . . . . . . . . . . . . .2513.2.  Informative References . . . . . . . . . . . . . . . . .28Appendix A.  Message Details  . . . . . . . . . . . . . . . . . .30A.1.  Signed Message  . . . . . . . . . . . . . . . . . . . . .30A.2.  Short Signed Message  . . . . . . . . . . . . . . . . . .32A.3.  Signed and Encrypted Message  . . . . . . . . . . . . . .33A.3.1.  Signed Message prior to Encryption  . . . . . . . . .33A.3.2.  Encrypted Message . . . . . . . . . . . . . . . . . .35   Authors' Addresses  . . . . . . . . . . . . . . . . . . . . . . .39Campbell & Housley           Standards Track                    [Page 3]

RFC 8591                S/MIME for SIP Messaging              April 20191.  Introduction   Several mobile messaging systems use the Session Initiation Protocol   (SIP) [RFC3261], typically as some combination of the SIP MESSAGE   method [RFC3428] and the Message Session Relay Protocol (MSRP)   [RFC4975].  For example, Voice over LTE (VoLTE) uses the SIP MESSAGE   method to send Short Message Service (SMS) messages.  The Open Mobile   Alliance (OMA) Converged IP Messaging (CPM) system [CPM] uses the SIP   MESSAGE method for short "pager mode" messages and uses MSRP for   large messages and for sessions of messages.  The Global System for   Mobile Communications Association (GSMA) Rich Communication Services   (RCS) uses CPM for messaging [RCS].   At the same time, organizations increasingly depend on mobile   messaging systems to send notifications to their customers.  Many of   these notifications are security sensitive.  For example, such   notifications are commonly used for notice of financial transactions,   notice of login or password change attempts, and the sending of   two-factor authentication codes.   Both SIP and MSRP can be used to transport any content using   Multipurpose Internet Mail Extensions (MIME) formats.  The SIP   MESSAGE method is typically limited to short messages (under   1300 octets for the MESSAGE request).  MSRP can carry arbitrarily   large messages and can break large messages into chunks.   While both SIP and MSRP provide mechanisms for hop-by-hop security,   neither provides native end-to-end protection.  Instead, they depend   on S/MIME [RFC8550] [RFC8551].  However, at the time of this writing,   S/MIME is not in common use for SIP-based and MSRP-based messaging   services.  This document updates and clarifies RFCs 3261, 3428, and   4975 in an attempt to make S/MIME for SIP and MSRP easier to   implement and deploy in an interoperable fashion.   This document updates RFCs 3261, 3428, and 4975 to update the   cryptographic algorithm recommendations and the handling of S/MIME   data objects.  It updatesRFC 3261 to allow S/MIME signed messages to   be sent without embedded certificates in some situations.  Finally,   it updates RFCs 3261, 3428, and 4975 to clarify error-reporting   requirements for certain situations.2.  Terminology   The key words "MUST", "MUST NOT", "REQUIRED", "SHALL", "SHALL NOT",   "SHOULD", "SHOULD NOT", "RECOMMENDED", "NOT RECOMMENDED", "MAY", and   "OPTIONAL" in this document are to be interpreted as described inBCP 14 [RFC2119] [RFC8174] when, and only when, they appear in all   capitals, as shown here.Campbell & Housley           Standards Track                    [Page 4]

RFC 8591                S/MIME for SIP Messaging              April 20193.  Problem Statement and Scope   This document discusses the use of S/MIME with SIP-based messaging.   Other standardized messaging protocols exist, such as the Extensible   Messaging and Presence Protocol (XMPP) [RFC6121].  Likewise, other   end-to-end protection formats exist, such as JSON Web Signatures   [RFC7515] and JSON Web Encryption [RFC7516].   This document focuses on SIP-based messaging because its use is   becoming more common in mobile environments.  It focuses on S/MIME,   since several mobile operating systems already have S/MIME libraries   installed.  While there may also be value in specifying end-to-end   security for other messaging and security mechanisms, it is out of   scope for this document.   MSRP sessions are negotiated using the Session Description Protocol   (SDP) [RFC4566] offer/answer mechanism [RFC3264] or similar   mechanisms.  This document assumes that SIP is used for the   offer/answer exchange.  However, the techniques should be adaptable   to other signaling protocols.   [RFC3261], [RFC3428], and [RFC4975] already describe the use of   S/MIME.  [RFC3853] updates SIP to support the Advanced Encryption   Standard (AES).  In aggregate, that guidance is incomplete, contains   inconsistencies, and is still out of date in terms of supported and   recommended algorithms.   The guidance inRFC 3261 is based on an implicit assumption that   S/MIME is being used to secure signaling applications.  That advice   is not entirely appropriate for messaging applications.  For example,   it assumes that message decryption always happens before the SIP   transaction completes.   This document offers normative updates and clarifications to the use   of S/MIME with the SIP MESSAGE method and MSRP.  It does not attempt   to define a complete secure messaging system.  Such a system would   require considerable work around user enrollment, certificate and key   generation and management, multi-party chats, device management, etc.   While nothing herein should preclude those efforts, they are out of   scope for this document.   This document primarily covers the sending of single messages -- for   example, "pager-mode messages" sent using the SIP MESSAGE method and   "large messages" sent in MSRP.  Techniques to use a common signing or   encryption key across a session of messages are out of scope for this   document.Campbell & Housley           Standards Track                    [Page 5]

RFC 8591                S/MIME for SIP Messaging              April 2019   Cryptographic algorithm requirements in this document are intended to   supplement those already specified for SIP and MSRP.4.  Applicability of S/MIME   The Cryptographic Message Syntax (CMS) [RFC5652] is an encapsulation   syntax that is used to digitally sign, digest, authenticate, or   encrypt arbitrary message content.  The CMS supports a variety of   architectures for certificate-based key management, especially the   one defined by the IETF PKIX (Public Key Infrastructure using X.509)   Working Group [RFC5280].  The CMS values are generated using ASN.1   [X680], using the Basic Encoding Rules (BER) and Distinguished   Encoding Rules (DER) [X690].   The S/MIME Message Specification [RFC8551] defines MIME body parts   based on the CMS.  In this document, the application/pkcs7-mime media   type is used to digitally sign an encapsulated body part, and it is   also used to encrypt an encapsulated body part.4.1.  Signed Messages   While both SIP and MSRP require support for the multipart/signed   format, the use of application/pkcs7-mime is RECOMMENDED for most   signed messages.  Experience with the use of S/MIME in electronic   mail has shown that multipart/signed bodies are at greater risk of   "helpful" tampering by intermediaries, a common cause of signature   validation failure.  This risk is also present for messaging   applications; for example, intermediaries might insert Instant   Message Disposition Notification (IMDN) requests [RFC5438] into   messages.  (SeeSection 9.2.)  The application/pkcs7-mime format is   also more compact, which can be important for messaging applications,   especially when using the SIP MESSAGE method.  (SeeSection 7.1.)   The use of multipart/signed may still make sense if the message needs   to be readable by receiving agents that do not support S/MIME.   When generating a signed message, sending User Agents (UAs) SHOULD   follow the conventions specified in [RFC8551] for the   application/pkcs7-mime media type with smime-type=signed-data.  When   validating a signed message, receiving UAs MUST follow the   conventions specified in [RFC8551] for the application/pkcs7-mime   media type with smime-type=signed-data.Campbell & Housley           Standards Track                    [Page 6]

RFC 8591                S/MIME for SIP Messaging              April 2019   Sending and receiving UAs MUST support the SHA-256 message digest   algorithm [RFC5754].  For convenience, the SHA-256 algorithm   identifier is repeated here:      id-sha256 OBJECT IDENTIFIER ::= {        joint-iso-itu-t(2) country(16) us(840) organization(1) gov(101)        csor(3) nistalgorithm(4) hashalgs(2) 1 }   Sending and receiving UAs MAY support other message digest   algorithms.   Sending and receiving UAs MUST support the Elliptic Curve Digital   Signature Algorithm (ECDSA) using the NIST P-256 elliptic curve and   the SHA-256 message digest algorithm [RFC5480] [RFC5753].  Sending   and receiving UAs SHOULD support the Edwards-curve Digital Signature   Algorithm (EdDSA) with curve25519 (Ed25519) [RFC8032] [RFC8419].  For   convenience, the ECDSA with SHA-256 algorithm identifier, the object   identifier for the well-known NIST P-256 elliptic curve, and the   Ed25519 algorithm identifier are repeated here:      ecdsa-with-SHA256 OBJECT IDENTIFIER ::= {        iso(1) member-body(2) us(840) ansi-X9-62(10045) signatures(4)        ecdsa-with-SHA2(3) 2 }      -- Note: The NIST P-256 elliptic curve is also known as secp256r1.      secp256r1 OBJECT IDENTIFIER ::= {        iso(1) member-body(2) us(840) ansi-X9-62(10045) curves(3)        prime(1) 7 }      id-Ed25519  OBJECT IDENTIFIER  ::=  {        iso(1) identified-organization(3) thawte(101) 112 }4.2.  Encrypted Messages   When generating an encrypted message, sending UAs MUST follow the   conventions specified in [RFC8551] for the application/pkcs7-mime   media type with smime-type=auth-enveloped-data.  When decrypting a   received message, receiving UAs MUST follow the conventions specified   in [RFC8551] for the application/pkcs7-mime media type with   smime-type=auth-enveloped-data.Campbell & Housley           Standards Track                    [Page 7]

RFC 8591                S/MIME for SIP Messaging              April 2019   Sending and receiving UAs MUST support the AES-128-GCM algorithm for   content encryption [RFC5084].  For convenience, the AES-128-GCM   algorithm identifier is repeated here:      id-aes128-GCM OBJECT IDENTIFIER ::=  {        joint-iso-itu-t(2) country(16) us(840) organization(1) gov(101)        csor(3) nistAlgorithm(4) aes(1) 6 }   Sending and receiving UAs MAY support other content-authenticated   encryption algorithms.   Sending and receiving UAs MUST support the AES-128-WRAP algorithm for   encryption of one AES key with another AES key [RFC3565].  For   convenience, the AES-128-WRAP algorithm identifier is repeated here:      id-aes128-wrap OBJECT IDENTIFIER ::=  {        joint-iso-itu-t(2) country(16) us(840) organization(1) gov(101)        csor(3) nistAlgorithm(4) aes(1) 5 }   Sending and receiving UAs MAY support other key-encryption   algorithms.   Symmetric key-encryption keys can be distributed before messages are   sent.  If sending and receiving UAs support previously distributed   key-encryption keys, then they MUST assign a KEKIdentifier [RFC5652]   to the previously distributed symmetric key.   Alternatively, a key agreement algorithm can be used to establish a   single-use key-encryption key.  If sending and receiving UAs support   key agreement, then they MUST support the Elliptic Curve   Diffie-Hellman (ECDH) algorithm using the NIST P-256 elliptic curve   and the ANSI-X9.63-KDF key derivation function with the SHA-256   message digest algorithm [RFC5753].  If sending and receiving UAs   support key agreement, then they SHOULD support the ECDH algorithm   using curve25519 (X25519) [RFC7748] [RFC8418].  For convenience,   (1) the identifier for the ECDH algorithm using the ANSI-X9.63-KDF   with the SHA-256 algorithm and (2) the identifier for the X25519   algorithm are repeated here:      dhSinglePass-stdDH-sha256kdf-scheme OBJECT IDENTIFIER ::= {        iso(1) identified-organization(3) certicom(132)        schemes(1) 11 1 }      id-X25519 OBJECT IDENTIFIER ::= {        iso(1) identified-organization(3) thawte(101) 110 }Campbell & Housley           Standards Track                    [Page 8]

RFC 8591                S/MIME for SIP Messaging              April 20194.3.  Signed and Encrypted MessagesRFC 3261, Section 23.2 says that when a User Agent Client (UAC) sends   signed and encrypted data, it "SHOULD" send an EnvelopedData object   encapsulated within a SignedData message.  That essentially says that   one should encrypt first, then sign.  This document updatesRFC 3261   to say that, when sending signed and encrypted user content in a SIP   MESSAGE request, the sending UAs MUST sign the message first, and   then encrypt it.  That is, it must send the SignedData object inside   an AuthEnvelopedData object.  For interoperability reasons,   recipients SHOULD accept messages signed and encrypted in either   order.4.4.  Certificate Handling   Sending and receiving UAs MUST follow the S/MIME certificate-handling   procedures [RFC8550], with a few exceptions detailed below.4.4.1.  Subject Alternative Name   In both SIP and MSRP, the identity of the sender of a message is   typically expressed as a SIP URI.   The subject alternative name extension is used as the preferred means   to convey the SIP URI of the subject of a certificate.  Any SIP URI   present MUST be encoded using the uniformResourceIdentifier CHOICE of   the GeneralName type as described in[RFC5280], Section 4.2.1.6.   Since the SubjectAltName type is a SEQUENCE OF GeneralName, multiple   URIs MAY be present.   Other methods of identifying a certificate subject MAY be used.4.4.2.  Certificate Validation   When validating a certificate, receiving UAs MUST support the ECDSA   using the NIST P-256 elliptic curve and the SHA-256 message digest   algorithm [RFC5480].   Sending and receiving UAs MAY support other digital signature   algorithms for certificate validation.5.  Transfer Encoding   SIP and MSRP UAs are always capable of receiving binary data.  Inner   S/MIME entities do not require base64 encoding [RFC4648].   Both SIP and MSRP provide 8-bit safe transport channels; base64   encoding is not generally needed for the outer S/MIME entities.Campbell & Housley           Standards Track                    [Page 9]

RFC 8591                S/MIME for SIP Messaging              April 2019   However, if there is a chance a message might cross a 7-bit transport   (for example, gateways that convert to a 7-bit transport for   intermediate transfer), base64 encoding may be needed for the outer   entity.6.  User Agent Capabilities   Messaging UAs may implement a subset of S/MIME capabilities.  Even   when implemented, some features may not be available due to   configuration.  For example, UAs that do not have user certificates   cannot sign messages on behalf of the user or decrypt encrypted   messages sent to the user.  At a minimum, a UA that supports S/MIME   MUST be able to validate a signed message.   End-user certificates have long been a barrier to large-scale S/MIME   deployment.  But since UAs can validate signatures even without local   certificates, the use case of organizations sending secure   notifications to their users becomes a sort of "low-hanging fruit".   That being said, the signed-notification use case still requires   shared trust anchors.   SIP and MSRP UAs advertise their level of support for S/MIME by   indicating their capability to receive the "application/pkcs7-mime"   media type.   The fact that a UA indicates support for the "multipart/signed" media   type does not necessarily imply support for S/MIME.  The UA might   just be able to display clear-signed content without validating the   signature.  UAs that wish to indicate the ability to validate   signatures for clear-signed messages MUST also indicate support for   "application/pkcs7-signature".   A UA can indicate that it can receive all smime-types by advertising   "application/pkcs7-mime" with no parameters.  If a UA does not accept   all smime-types, it advertises the media type with the appropriate   parameters.  If more than one smime-type is supported, the UA   includes a separate instance of the media-type string, appropriately   parameterized, for each.   For example, a UA that can only receive signed-data would advertise   "application/pkcs7-mime; smime-type=signed-data".   SIP signaling can fork to multiple destinations for a given Address   of Record (AoR).  A user might have multiple UAs with different   capabilities; the capabilities remembered from an interaction with   one such UA might not apply to another.  (SeeSection 7.2.)Campbell & Housley           Standards Track                   [Page 10]

RFC 8591                S/MIME for SIP Messaging              April 2019   UAs can also advertise or discover S/MIME using out-of-band   mechanisms.  Such mechanisms are beyond the scope of this document.7.  Using S/MIME with the SIP MESSAGE Method   The use of S/MIME with the SIP MESSAGE method is described inSection 11.3 of [RFC3428], and for SIP in general inSection 23 of   [RFC3261].  This section and its child sections offer clarifications   for the use of S/MIME with the SIP MESSAGE method, along with related   updates to RFCs 3261 and 3428.7.1.  Size Limit   SIP MESSAGE requests are typically limited to 1300 octets.  That   limit applies to the entire message, including both SIP header fields   and the message content.  This is due to the potential for   fragmentation of larger requests sent over UDP.  In general, it is   hard to be sure that no proxy or other intermediary will forward a   SIP request over UDP somewhere along the path.  Therefore, S/MIME   messages sent using the SIP MESSAGE method should be kept as small as   possible.  Messages that will not fit within the limit can be sent   using MSRP.Section 23.2 of [RFC3261] requires that a SignedData message contain   a certificate to be used to validate the signature.  In order to   reduce the message size, this document updates that text to say that   a SignedData message sent in a SIP MESSAGE request SHOULD contain the   certificate but MAY omit it if the sender has reason to believe that   the recipient (1) already has the certificate in its keychain or   (2) has some other method of accessing the certificate.7.2.  SIP User Agent Capabilities   SIP UAs can theoretically indicate support for S/MIME by including   the appropriate media type or types in the SIP Accept header field in   a response to an OPTIONS request, or in a 415 (Unsupported Media   Type) response to a SIP request that contained an unsupported media   type in the body.  Unfortunately, this approach may not be reliable   in the general case.  In the case where a downstream SIP proxy forks   an OPTIONS or other non-INVITE request to multiple User Agent Servers   (UASs), that proxy will only forward the "best" response.  If the   recipient has multiple devices, the sender may only learn the   capabilities of the device that sent the forwarded response.  Blindly   trusting this information could result in S/MIME messages being sent   to UAs that do not support it, which would be at best confusing and   at worst misleading to the recipient.Campbell & Housley           Standards Track                   [Page 11]

RFC 8591                S/MIME for SIP Messaging              April 2019   UAs might be able to use the UA capabilities framework [RFC3840] to   indicate support.  However, doing so would require the registration   of one or more media feature tags with IANA.   UAs MAY use other out-of-band methods to indicate their level of   support for S/MIME.7.3.  Failure CasesSection 23.2 of [RFC3261] requires that the recipient of a SIP   request that includes a body part of an unsupported media type and a   Content-Disposition header field "handling" parameter of "required"   return a 415 (Unsupported Media Type) response.  Given that SIP   MESSAGE exists for no reason other than to deliver content in the   body, it is reasonable to treat the top-level body part as always   required.  However, [RFC3428] makes no such assertion.  This document   updatesSection 11.3 of [RFC3428] to add the statement that a UAC   that receives a SIP MESSAGE request with an unsupported media type   MUST return a 415 response.Section 23.2 of [RFC3261] says that if a recipient receives an S/MIME   body encrypted to the wrong certificate, it MUST return a SIP 493   (Undecipherable) response and SHOULD send a valid certificate in that   response.  This is not always possible in practice for SIP MESSAGE   requests.  The UAS may choose not to decrypt a message until the user   is ready to read it.  Messages may be delivered to a message store or   sent via a store-and-forward service.  This document updatesRFC 3261   to say that the UAS SHOULD return a SIP 493 response if it   immediately attempts to decrypt the message and determines that the   message was encrypted to the wrong certificate.  However, it MAY   return a 200-class response if decryption is deferred.8.  Using S/MIME with MSRP   MSRP has features that interact with the use of S/MIME.  In   particular, the ability to send messages in chunks, the ability to   send messages of unknown size, and the use of SDP to indicate   media-type support create considerations for the use of S/MIME.8.1.  Chunking   MSRP allows a message to be broken into "chunks" for transmission.   In this context, the term "message" refers to an entire message that   one user might send to another.  A chunk is a fragment of that   message sent in a single MSRP SEND request.  All of the chunks that   make up a particular message share the same Message-ID value.Campbell & Housley           Standards Track                   [Page 12]

RFC 8591                S/MIME for SIP Messaging              April 2019   The sending UA may break a message into chunks, which the receiving   UA will reassemble to form the complete message.  Intermediaries such   as MSRP relays [RFC4976] might break chunks into smaller chunks or   might reassemble chunks into larger ones; therefore, the message   received by the recipient may be broken into a different number of   chunks than were sent by the recipient.  Intermediaries might also   cause chunks to be received in a different order than sent.   The sender MUST apply any S/MIME operations to the whole message   prior to breaking it into chunks.  Likewise, the receiver needs to   reassemble the message from its chunks prior to decrypting,   validating a signature, etc.   MSRP chunks are framed using an end-line.  The end-line comprises   seven hyphens, a 64-bit random value taken from the start line, and a   continuation flag.  MSRP requires the sending UA to scan data to be   sent in a specific chunk to ensure that the end-line does not   accidentally occur as part of the data.  This scanning occurs on a   chunk rather than a whole message; consequently, it must occur after   the sender applies any S/MIME operations.8.2.  Streamed Data   MSRP allows a mode of operation where a UA sends some chunks of a   message prior to knowing the full length of the message.  For   example, a sender might send streamed data over MSRP as a single   message, even though it doesn't know the full length of that data in   advance.  This mode is incompatible with S/MIME, since a sending UA   must apply S/MIME operations to the entire message in advance of   breaking it into chunks.   Therefore, when sending a message in an S/MIME format, the sender   MUST include the Byte-Range header field for every chunk, including   the first chunk.  The Byte-Range header field MUST include the total   length of the message.   A higher layer could choose to break such streamed data into a series   of messages prior to applying S/MIME operations, so that each   fragment appears as a distinct (separate) S/MIME message in MSRP.   Such mechanisms are beyond the scope of this document.Campbell & Housley           Standards Track                   [Page 13]

RFC 8591                S/MIME for SIP Messaging              April 20198.3.  Indicating Support for S/MIME   A UA that supports this specification MUST explicitly include the   appropriate media type or types in the "accept-types" attribute in   any SDP offer or answer that proposes MSRP.  It MAY indicate that it   requires S/MIME wrappers for all messages by putting appropriate   S/MIME media types in the "accept-types" attribute and putting all   other supported media types in the "accept-wrapped-types" attribute.   For backwards compatibility, a sender MAY treat a peer that includes   an asterisk ("*") in the "accept-types" attribute as potentially   supporting S/MIME.  If the peer returns an MSRP 415 (MIME type not   understood) response to an attempt to send an S/MIME message, the   sender should treat the peer as not supporting S/MIME for the   duration of the session, as indicated inSection 7.3.1 of [RFC4975].   While these SDP attributes allow an endpoint to express support for   certain media types only when wrapped in a specified envelope type,   it does not allow the expression of more complex structures.  For   example, an endpoint can say that it supports text/plain and   text/html, but only when inside an application/pkcs7 or message/cpim   container, but it cannot express a requirement for the leaf types to   always be contained in an application/pkcs7 container nested inside a   message/cpim container.  This has implications for the use of S/MIME   with the message/cpim format.  (SeeSection 9.1.)   MSRP allows multiple reporting modes that provide different levels of   feedback.  If the sender includes a Failure-Report header field with   a value of "no", it will not receive failure reports.  This mode   should not be used carelessly, since such a sender would never see a   415 response as described above and would have no way to learn that   the recipient could not process an S/MIME body.8.4.  MSRP URIs   MSRP URIs are ephemeral.  Endpoints MUST NOT use MSRP URIs to   identify certificates or insert MSRP URIs into certificate Subject   Alternative Name fields.  When MSRP sessions are negotiated using SIP   [RFC3261], the SIP AoRs of the peers are used instead.   Note that MSRP allows messages to be sent between peers in either   direction.  A given MSRP message might be sent from the SIP offerer   to the SIP answerer.  Thus, the sender and recipient roles may   reverse between one message and another in a given session.Campbell & Housley           Standards Track                   [Page 14]

RFC 8591                S/MIME for SIP Messaging              April 20198.5.  Failure Cases   Successful delivery of an S/MIME message does not indicate that the   recipient successfully decrypted the contents or validated a   signature.  Decryption and/or validation may not occur immediately on   receipt, since the recipient may not immediately view the message,   and the UA may choose not to attempt decryption or validation until   the user requests it.   Likewise, successful delivery of S/MIME enveloped data does not, on   its own, indicate that the recipient supports the enclosed media   type.  If the peer only implicitly indicated support for the enclosed   media type through the use of a wildcard in the "accept-types" or   "accept-wrapped types" SDP attributes, it may not decrypt the message   in time to send a 415 response.9.  S/MIME Interaction with Other SIP Messaging Features9.1.  Common Profile for Instant Messaging   The Common Profile for Instant Messaging (CPIM) [RFC3860] defines an   abstract messaging service, with the goal of creating gateways   between different messaging protocols that could relay instant   messages without change.  The SIP MESSAGE method and MSRP were   initially designed to map to the CPIM abstractions.  However, at the   time of this writing, CPIM-compliant gateways have not been deployed.   To the authors' knowledge, no other IM protocols have been explicitly   mapped to CPIM.   CPIM also defines the abstract messaging URI scheme "im:".  As of the   time of this writing, the "im:" scheme is not in common use.   The CPIM message format [RFC3862] allows UAs to attach   transport-neutral metadata to arbitrary MIME content.  The format was   designed as a canonicalization format to allow signed data to cross   protocol-converting gateways without loss of metadata needed to   verify the signature.  While it has not typically been used for that   purpose, it has been used for other metadata applications -- for   example, IMDNs [RFC5438] and MSRP multi-party chat [RFC7701].   In the general case, a sender applies end-to-end signature and   encryption operations to the entire MIME body.  However, some   messaging systems expect to inspect and in some cases add or modify   metadata in CPIM header fields.  For example, CPM-based and RCS-based   services include application servers that may need to insert   timestamps into chat messages and may use additional metadata to   characterize the content and purpose of a message to determine   application behavior.  The former will cause validation failure forCampbell & Housley           Standards Track                   [Page 15]

RFC 8591                S/MIME for SIP Messaging              April 2019   signatures that cover CPIM metadata, while the latter is not possible   if the metadata is encrypted.  Clients intended for use in such   networks MAY choose to apply end-to-end signatures and encryption   operations to only the CPIM payload, leaving the CPIM metadata   unprotected from inspection and modification.  UAs that support   S/MIME and CPIM SHOULD be able to validate signatures and decrypt   enveloped data both (1) when those operations are applied to the   entire CPIM body and (2) when they are applied to just the CPIM   payload.  This means that the receiver needs to be flexible in its   MIME document parsing and that it cannot make assumptions that   S/MIME-protected body parts will always be in the same position or   level in the message payload.   If such clients need to encrypt or sign CPIM metadata end to end,   they can nest a protected CPIM message format payload inside an   unprotected CPIM message envelope.   The use of CPIM metadata fields to identify certificates or to   authenticate SIP or MSRP header fields is out of scope for this   document.9.2.  Instant Message Disposition Notifications   The IMDN mechanism [RFC5438] allows both endpoints and intermediary   application servers to request and to generate delivery   notifications.  The use of S/MIME does not impact strictly end-to-end   use of IMDNs.  The IMDN mechanism recommends that devices that are   capable of doing so sign delivery notifications.  It further requires   that delivery notifications that result from encrypted messages also   be encrypted.   However, the IMDN mechanism allows intermediary application servers   to insert notification requests into messages, to add routing   information to messages, and to act on notification requests.  It   also allows list servers to aggregate delivery notifications.   Such intermediaries will be unable to read end-to-end encrypted   messages in order to interpret delivery notice requests.   Intermediaries that insert information into end-to-end signed   messages will cause the signature validation to fail.  (SeeSection 9.1.)Campbell & Housley           Standards Track                   [Page 16]

RFC 8591                S/MIME for SIP Messaging              April 201910.  Examples   The following sections show examples of S/MIME messages in SIP and   MSRP.  The examples include the tags "[start-hex]" and "[end-hex]" to   denote binary content shown in hexadecimal.  The tags are not part of   the actual message and do not count towards the Content-Length header   field values.   In all of these examples, the cleartext message is the string   "Watson, come here - I want to see you." followed by a newline   character.   The cast of characters includes Alice, with a SIP AoR of   "alice@example.com", and Bob, with a SIP AoR of "bob@example.org".Appendix A shows the detailed content of each S/MIME body.10.1.  Signed Message in SIP including the Sender's Certificate   Figure 1 shows a message signed by Alice.  This body uses the   "application/pkcs7-mime" media type with an smime-type parameter   value of "signed-data".   The S/MIME body includes Alice's signing certificate.  Even though   the original message content is fairly short and only minimal SIP   header fields are included, the total message size approaches the   maximum allowed for the SIP MESSAGE method unless the UAC has advance   knowledge that all SIP hops will use congestion-controlled transport   protocols.  A message that included all the SIP header fields that   are commonly in use in some SIP deployments would likely exceed the   limit.Campbell & Housley           Standards Track                   [Page 17]

RFC 8591                S/MIME for SIP Messaging              April 2019   MESSAGE sip:bob@example.org SIP/2.0   Via: SIP/2.0/TCP alice-pc.example.com;branch=z9hG4bK776sgdkfie   Max-Forwards: 70   From: sip:alice@example.com;tag=49597   To: sip:bob@example.org   Call-ID: asd88asd66b@1.2.3.4   CSeq: 1 MESSAGE   Content-Transfer-Encoding: binary   Content-Type: application/pkcs7-mime; smime-type=signed-data;                 name="smime.p7m"   Content-Disposition: attachment; filename="smime.p7m"   Content-Length: 762   [start-hex]   308202f606092a864886f70d010702a08202e7308202e3020101310d300b0609   608648016503040201305306092a864886f70d010701a0460444436f6e74656e   742d547970653a20746578742f706c61696e0d0a0d0a576174736f6e2c20636f   6d652068657265202d20492077616e7420746f2073656520796f752e0d0aa082   016b308201673082010da003020102020900b8793ec0e4c21530300a06082a86   48ce3d040302302631143012060355040a0c0b6578616d706c652e636f6d310e   300c06035504030c05416c696365301e170d3137313231393233313230355a17   0d3138313231393233313230355a302631143012060355040a0c0b6578616d70   6c652e636f6d310e300c06035504030c05416c6963653059301306072a8648ce   3d020106082a8648ce3d03010703420004d87b54729f2c22feebd9ddba0efa40   642297a6093887a4dae7990b23f87fa7ed99db8cf5a314f2ee64106ef1ed61db   fc0a4b91c953cbd022a751b914807bb794a324302230200603551d1104193017   86157369703a616c696365406578616d706c652e636f6d300a06082a8648ce3d   040302034800304502207879be1c27f846276fdf15e333e53c6f17a757388a02   cb7b8ae481c1641ae7a9022100ff99cd9c94076c82b02fea3b1350179a4b7752   e16fa30a3f9ab29650b0e2818931820109308201050201013033302631143012   060355040a0c0b6578616d706c652e636f6d310e300c06035504030c05416c69   6365020900b8793ec0e4c21530300b0609608648016503040201a06930180609   2a864886f70d010903310b06092a864886f70d010701301c06092a864886f70d   010905310f170d3139303132363036313335345a302f06092a864886f70d0109   0431220420ef778fc940d5e6dc2576f47a599b3126195a9f1a227adaf35fa22c   050d8d195a300a06082a8648ce3d04030204473045022005fdc2b55b0f444a46   be468dfc7ef3b7de30019ef0952a223e8521890b35bb4e02210090e43a9d9846   cf2af8159c5c0ef48848fa2f39f998b1bb99b52a6fc6c776f2c8   [end-hex]                      Figure 1: Signed Message in SIPCampbell & Housley           Standards Track                   [Page 18]

RFC 8591                S/MIME for SIP Messaging              April 201910.2.  Signed Message in SIP with No Certificate   Figure 2 shows the same message from Alice without the embedded   certificate.  The shorter total message length may be more   manageable.   MESSAGE sip:bob@example.org SIP/2.0   Via: SIP/2.0/TCP alice-pc.example.com;branch=z9hG4bK776sgdkfie   Max-Forwards: 70   From: sip:alice@example.com;tag=49597   To: sip:bob@example.org   Call-ID: asd88asd66b@1.2.3.4   CSeq: 1 MESSAGE   Content-Transfer-Encoding: binary   Content-Type: application/pkcs7-mime; smime-type=signed-data;                 name="smime.p7m"   Content-Disposition: attachment; filename="smime.p7m"   Content-Length: 395   [start-hex]   3082018706092a864886f70d010702a082017830820174020101310d300b0609   608648016503040201305306092a864886f70d010701a0460444436f6e74656e   742d547970653a20746578742f706c61696e0d0a0d0a576174736f6e2c20636f   6d652068657265202d20492077616e7420746f2073656520796f752e0d0a3182   0109308201050201013033302631143012060355040a0c0b6578616d706c652e   636f6d310e300c06035504030c05416c696365020900b8793ec0e4c21530300b   0609608648016503040201a069301806092a864886f70d010903310b06092a86   4886f70d010701301c06092a864886f70d010905310f170d3139303132363036   313335345a302f06092a864886f70d01090431220420ef778fc940d5e6dc2576   f47a599b3126195a9f1a227adaf35fa22c050d8d195a300a06082a8648ce3d04   03020447304502203607275592d30c8c5a931041a01804d60c638ac9a8080918   87172a0887c8d4aa022100cd9e14bd21817336e9052fe590af2e2bcde16dd3e9   48d0f5f78a969e26382682   [end-hex]       Figure 2: Signed Message in SIP with No Certificate IncludedCampbell & Housley           Standards Track                   [Page 19]

RFC 8591                S/MIME for SIP Messaging              April 201910.3.  MSRP Signed and Encrypted Message in a Single Chunk   Figure 3 shows a signed and encrypted message from Bob to Alice sent   via MSRP.   MSRP dsdfoe38sd SEND   To-Path: msrp://alicepc.example.com:7777/iau39soe2843z;tcp   From-Path: msrp://bobpc.example.org:8888/9di4eae923wzd;tcp   Message-ID: 456so39s   Byte-Range: 1-1940/1940   Content-Disposition: attachment; filename="smime.p7m"   Content-Type: application/pkcs7-mime; smime-type=auth-enveloped-data;                 name="smime.p7m"   [start-hex]   30820790060b2a864886f70d0109100117a082077f3082077b0201003182024f   3082024b0201003033302631143012060355040a0c0b6578616d706c652e636f   6d310e300c06035504030c05416c69636502090083f50bb70bd5c40e300d0609   2a864886f70d010101050004820200759a61b4ddf1f1af24668005635e476110   fa2723c1b9e45484b6d33e8387de967dc5e0cafb35571a56a1975cb550e7be31   c131da80fb731024845babb8d64cac26040424d9330561c843999415dd644b3c   ad95072f71451393c99f282c4883bd0ccc5dd54b931464e00a6e55e592c51a68   de1062516ec7d3ca8e764bb8ac789a88377765ef8dc36c0a6ed3ecae5285cac6   a29d5059445719a1bdcf906e0ff37e2c2ef0f4ec6225100cc062e1c748963bbc   88b8e3dfcf714073729dd5c7583e758acf3d186f2fa417be22c37c9a76c6b427   29aad27f73ae44ac98474d1eeb48948c12a403d0b3ce08a218d6af456924897c   c5c9664f6dfeb3f18141158dfc3b84090aa60380aa865137e1699c5c81974167   9d7a3c90ba79e6d7d5c8d89bb54a667423e43b0b7d6f78c0b4ab67bc343662a6   35fe595f1149c53950cac2e0ba318c227e6f76a8d940400fd3d3ea1c8ecea003   dcce2f1fb00f5cea335de1303fcbf93d8e1cbfd682f19beb624bacd1d7b8f580   f114a13b890894fb4044a5daa764b7f8c5ff92949452b35aeb9639b8ad63c051   5c95ccc6f823c2201067ea2262413fef397d48f7b6143f842ae8e1a48cad3ae0   1abaa3cf9ee7e36620e05cca0611bfac00eef1a498f2d259b9f0f7da83ef6f1b   061f387c2dc48c8b5dbaca862308f32f47925165c9e5ebb467799884918dd697   b447f4c407989b889b0c2e9580af783082050f06092a864886f70d010701301e   06096086480165030401063011040c4d8757222eac5294117f0c120201108082   04e0fe2fb3de0bf06998c39bf4a952fabf8b0fee3d7e2e85181aecf1a89e1a2e   decd9404885612dfc6984334d8602b7749b2504e45f57c3b066626b0fc746236   1eec267c560139be5cd286a2af9696cf51852278e52c3818cab0a68c598de4fc   e14a333884e4de5ddf57edd78867027a31e4a7c0c0299144c5de6bae39699e70   0e057eb0f0dad73b8b369f42eb321b41538781d982a11a0b3943ac10c97b54ee   b73b38ec131afc5610e373487274d69cafa9541902886c64f6962d42eb33f904   1a4ae11b88dc6958d53df50b8bb52aa35e2299885d0aae416b86f0a88d0eb7a9   81dbb283e8b94e9d50bf6265c2348a18a169aacb5a37a529bda2f9cb10efddcf   14231095d87964637bd33fb13c68b4cff9a1906960c1ea2301d325b7a15c5829   f3ea038f24df6b23180377d37131f75db18f41f9d85b653dfa46bf2617126326   ccf1cb833457752352c8417a094484d7b64bcf51b26a9beb3a0ed4b9caf1bd23   c690c654f7eb9ce9852e2f6d068eef8ba33bc6c4dddca7aef4d3574737d7c4dcCampbell & Housley           Standards Track                   [Page 20]

RFC 8591                S/MIME for SIP Messaging              April 2019   1e93770d8f4f22dea61d73083c32c4038c1eb3dd3383a89a8795e241c2ed7cb6   80758c041069489860fc9f490e85236072548b3249698f99953acf1ec658b7aa   85e554c449701a6d4b039ed103dc458df4b29cb04b8cedd540c84348da79c186   56d5188f9f3a9e4b9b840c70664b90296c60b7ac984e918d48a09dbddfb281fc   862510db59d9fa9dc93f10f9c6d7bef72931d184cad7ac13c1a5295fc89fe3bb   7eb8e02085a828c5a138786e607ade4f5e8d4115909209ba878a79305a5316c2   2229e42b886d06481c8473f9d51269e2af6341bce20f768e860d7784ed46150e   04ff50cd209c5b127511369fe06bc4aa9a72d8f1fe4fcf0866d664b365ffa86e   8c1b43e7a9212aecc16ca350a28efae25fac054dd934bfe7e5fa4f753aa41596   8c7ebec439e0ac0270b4874a068d22484c09d9e8abe17f1372b4b2f65f1148e8   933eda92e5d1774564963b391c3bbd9f1c27ffe36f832e05155fc39ee6652fa7   b4188975ec5c67b32c9f213c8ac6b8e132a5a7c3bf74f016405cd8c201d10521   93e186d44358de388d73211ba2f1792f3cfeb9bbde7211d26f56ab06e11ccc9c   cde2b88cd8373773eafc37fd85b7a7a2bcaec752e617d6e01c02b86e9d9a40f3   20462c5d66f8351716dcd6014bdf30a60f75fc0631c920845ed8c0bad35ddf19   84f2241cd3b529dc1028845f8089543df4f1441ede36b1bf31af5afc8c2b708d   50b645d4e7db88648c3eefe14765158fb0e8d3bb53ddcbe26d7124c6e1d992f8   3230aa953376ee8c68109568e8571f0c9bbda48f4df306fe747f371175148f31   832767cd766cf07b450cbf62cad2a7bd71f1f88233f116a1a7f3caf12f34bcf4   0d21e79ffc9827221b68b080ff03ad782d6d6d07871676f798943e54f13fd75c   89c0b4263bf10f56243f9e72ef3b3899a539d9a3ac5be2b69400a3cf8d196c5c   ed697b2ed803b987a5ee85c5095b48da7a5b03b47e2b9fe4cd4bc3098e864e0c   e7d467da99cd7f3a9e947b5eea77f7a6be16c8c7e9e0decc1ff132559c234321   7b9c2950386e85d2942121086cdfa19658195be6d7f86bca9881b695082964f1   2e7cf801025d6792c6882409414d703321ec83abd698d68956118713a0ff1272   acbc9a6d148900c74c16921df9b38f29ec46d4f10060fffe5e36bbbacaf2d1ba   d7dd057ed3e30ebcd69083f9d3a2a26ef90b751d6a1adfa0590db19da107cf3e   a8db0410f6ffc6e1aef19cd23d985a921976352d   [end-hex]   -------dsdfoe38sd$              Figure 3: Signed and Encrypted Message in MSRP10.4.  MSRP Signed and Encrypted Message Sent in Multiple Chunks   Figure 4 shows the same message as in Figure 3 except that the   message is broken into two chunks.  The S/MIME operations were   performed prior to breaking the message into chunks.   MSRP d93kswow SEND   To-Path: msrp://alicepc.example.com:7777/iau39soe2843z;tcp   From-Path: msrp://bobpc.example.org:8888/9di4eae923wzd;tcp   Message-ID: 12339sdqwer   Byte-Range: 1-960/1940   Content-Disposition: attachment; filename="smime.p7m"   Content-Type: application/pkcs7-mime; smime-type=enveloped-data;                 name="smime.p7m"Campbell & Housley           Standards Track                   [Page 21]

RFC 8591                S/MIME for SIP Messaging              April 2019   [start-hex]   30820790060b2a864886f70d0109100117a082077f3082077b0201003182024f   3082024b0201003033302631143012060355040a0c0b6578616d706c652e636f   6d310e300c06035504030c05416c69636502090083f50bb70bd5c40e300d0609   2a864886f70d010101050004820200759a61b4ddf1f1af24668005635e476110   fa2723c1b9e45484b6d33e8387de967dc5e0cafb35571a56a1975cb550e7be31   c131da80fb731024845babb8d64cac26040424d9330561c843999415dd644b3c   ad95072f71451393c99f282c4883bd0ccc5dd54b931464e00a6e55e592c51a68   de1062516ec7d3ca8e764bb8ac789a88377765ef8dc36c0a6ed3ecae5285cac6   a29d5059445719a1bdcf906e0ff37e2c2ef0f4ec6225100cc062e1c748963bbc   88b8e3dfcf714073729dd5c7583e758acf3d186f2fa417be22c37c9a76c6b427   29aad27f73ae44ac98474d1eeb48948c12a403d0b3ce08a218d6af456924897c   c5c9664f6dfeb3f18141158dfc3b84090aa60380aa865137e1699c5c81974167   9d7a3c90ba79e6d7d5c8d89bb54a667423e43b0b7d6f78c0b4ab67bc343662a6   35fe595f1149c53950cac2e0ba318c227e6f76a8d940400fd3d3ea1c8ecea003   dcce2f1fb00f5cea335de1303fcbf93d8e1cbfd682f19beb624bacd1d7b8f580   f114a13b890894fb4044a5daa764b7f8c5ff92949452b35aeb9639b8ad63c051   5c95ccc6f823c2201067ea2262413fef397d48f7b6143f842ae8e1a48cad3ae0   1abaa3cf9ee7e36620e05cca0611bfac00eef1a498f2d259b9f0f7da83ef6f1b   061f387c2dc48c8b5dbaca862308f32f47925165c9e5ebb467799884918dd697   b447f4c407989b889b0c2e9580af783082050f06092a864886f70d010701301e   06096086480165030401063011040c4d8757222eac5294117f0c120201108082   04e0fe2fb3de0bf06998c39bf4a952fabf8b0fee3d7e2e85181aecf1a89e1a2e   decd9404885612dfc6984334d8602b7749b2504e45f57c3b066626b0fc746236   1eec267c560139be5cd286a2af9696cf51852278e52c3818cab0a68c598de4fc   e14a333884e4de5ddf57edd78867027a31e4a7c0c0299144c5de6bae39699e70   0e057eb0f0dad73b8b369f42eb321b41538781d982a11a0b3943ac10c97b54ee   b73b38ec131afc5610e373487274d69cafa9541902886c64f6962d42eb33f904   1a4ae11b88dc6958d53df50b8bb52aa35e2299885d0aae416b86f0a88d0eb7a9   81dbb283e8b94e9d50bf6265c2348a18a169aacb5a37a529bda2f9cb10efddcf   14231095d87964637bd33fb13c68b4cff9a1906960c1ea2301d325b7a15c5829   [end-hex]   -------d93kswow+   MSRP op2nc9a SEND   To-Path: msrp://alicepc.example.com:8888/9di4eae923wzd;tcp   From-Path: msrp://bobpc.example.org:7654/iau39soe2843z;tcp   Message-ID: 12339sdqwer   Byte-Range: 961-1940/1940   Content-Disposition: attachment; filename="smime.p7m"   Content-Type: application/pkcs7-mime; smime-type=enveloped-data;                 name="smime.p7m"Campbell & Housley           Standards Track                   [Page 22]

RFC 8591                S/MIME for SIP Messaging              April 2019   [start-hex]   f3ea038f24df6b23180377d37131f75db18f41f9d85b653dfa46bf2617126326   ccf1cb833457752352c8417a094484d7b64bcf51b26a9beb3a0ed4b9caf1bd23   c690c654f7eb9ce9852e2f6d068eef8ba33bc6c4dddca7aef4d3574737d7c4dc   1e93770d8f4f22dea61d73083c32c4038c1eb3dd3383a89a8795e241c2ed7cb6   80758c041069489860fc9f490e85236072548b3249698f99953acf1ec658b7aa   85e554c449701a6d4b039ed103dc458df4b29cb04b8cedd540c84348da79c186   56d5188f9f3a9e4b9b840c70664b90296c60b7ac984e918d48a09dbddfb281fc   862510db59d9fa9dc93f10f9c6d7bef72931d184cad7ac13c1a5295fc89fe3bb   7eb8e02085a828c5a138786e607ade4f5e8d4115909209ba878a79305a5316c2   2229e42b886d06481c8473f9d51269e2af6341bce20f768e860d7784ed46150e   04ff50cd209c5b127511369fe06bc4aa9a72d8f1fe4fcf0866d664b365ffa86e   8c1b43e7a9212aecc16ca350a28efae25fac054dd934bfe7e5fa4f753aa41596   8c7ebec439e0ac0270b4874a068d22484c09d9e8abe17f1372b4b2f65f1148e8   933eda92e5d1774564963b391c3bbd9f1c27ffe36f832e05155fc39ee6652fa7   b4188975ec5c67b32c9f213c8ac6b8e132a5a7c3bf74f016405cd8c201d10521   93e186d44358de388d73211ba2f1792f3cfeb9bbde7211d26f56ab06e11ccc9c   cde2b88cd8373773eafc37fd85b7a7a2bcaec752e617d6e01c02b86e9d9a40f3   20462c5d66f8351716dcd6014bdf30a60f75fc0631c920845ed8c0bad35ddf19   84f2241cd3b529dc1028845f8089543df4f1441ede36b1bf31af5afc8c2b708d   50b645d4e7db88648c3eefe14765158fb0e8d3bb53ddcbe26d7124c6e1d992f8   3230aa953376ee8c68109568e8571f0c9bbda48f4df306fe747f371175148f31   832767cd766cf07b450cbf62cad2a7bd71f1f88233f116a1a7f3caf12f34bcf4   0d21e79ffc9827221b68b080ff03ad782d6d6d07871676f798943e54f13fd75c   89c0b4263bf10f56243f9e72ef3b3899a539d9a3ac5be2b69400a3cf8d196c5c   ed697b2ed803b987a5ee85c5095b48da7a5b03b47e2b9fe4cd4bc3098e864e0c   e7d467da99cd7f3a9e947b5eea77f7a6be16c8c7e9e0decc1ff132559c234321   7b9c2950386e85d2942121086cdfa19658195be6d7f86bca9881b695082964f1   2e7cf801025d6792c6882409414d703321ec83abd698d68956118713a0ff1272   acbc9a6d148900c74c16921df9b38f29ec46d4f10060fffe5e36bbbacaf2d1ba   d7dd057ed3e30ebcd69083f9d3a2a26ef90b751d6a1adfa0590db19da107cf3e   a8db0410f6ffc6e1aef19cd23d985a921976352d   [end-hex]   -------op2nc9a$           Figure 4: Signed, Encrypted, and Chunked MSRP Message11.  IANA Considerations   This document has no IANA actions.12.  Security Considerations   The security considerations for S/MIME [RFC8550] [RFC8551] and   elliptic curves in CMS [RFC5753] apply.  The S/MIME-related security   considerations for SIP [RFC3261], SIP MESSAGE [RFC3428], and MSRP   [RFC4975] apply.Campbell & Housley           Standards Track                   [Page 23]

RFC 8591                S/MIME for SIP Messaging              April 2019   The security considerations for algorithms recommended in this   document also apply; see [RFC3565], [RFC5480], [RFC5753], [RFC5754],   [RFC7748], [RFC8032], [RFC8418], and [RFC8419].   This document assumes that end-entity certificate validation is   provided by a chain of trust to a certification authority (CA), using   a public key infrastructure.  The security considerations from   [RFC5280] apply.  However, other validations methods may be possible   -- for example, sending a signed fingerprint for the end entity in   SDP.  The relationship between this work and the techniques discussed   in [RFC8224] and [RTP-Sec] are out of scope for this document.   When matching an end-entity certificate to the sender or recipient   identity, the respective SIP AoRs are used.  Typically, these will   match the SIP From and To header fields.  Some UAs may extract the   sender identity from SIP AoRs in other header fields -- for example,   P-Asserted-Identity [RFC3325].  In general, the UAS should compare   the certificate to the identity that it relies upon -- for example,   for display to the end user or comparison against message-filtering   rules.   The secure notification use case discussed inSection 1 has   significant vulnerabilities when used in an insecure environment.   For example, "phishing" messages could be used to trick users into   revealing credentials.  Eavesdroppers could learn confirmation codes   from unprotected two-factor authentication messages.  Unsolicited   messages sent by impersonators could tarnish the reputation of an   organization.  While hop-by-hop protection can mitigate some of those   risks, it still leaves messages vulnerable to malicious or   compromised intermediaries.  End-to-end protection prevents   modification by intermediaries.  However, neither provides much   protection unless the recipient knows to expect messages from a   particular sender to be signed and refuses to accept unsigned   messages that appear to be from that source.   Mobile messaging is typically an online application; online   certificate revocation checks should usually be feasible.   S/MIME does not normally protect the SIP or MSRP headers.  While it   normally does protect the CPIM header, certain CPIM header fields may   not be protected if the sender excludes them from the encrypted or   signed part of the message.  (SeeSection 9.1.)  Certain messaging   services -- for example, those based on RCS -- may include   intermediaries that attach metadata to user-generated messages in the   form of SIP, MSRP, or CPIM header fields.  This metadata could   possibly reveal information to third parties that the sender mightCampbell & Housley           Standards Track                   [Page 24]

RFC 8591                S/MIME for SIP Messaging              April 2019   prefer not to send as cleartext.  Implementors and operators should   consider whether inserted metadata may create privacy leaks.  Such an   analysis is beyond the scope of this document.   MSRP messages broken into chunks must be reassembled by the recipient   prior to decrypting or validation of signatures.  (SeeSection 8.1.)Section 14.5 of [RFC4975] describes a potential denial-of-service   attack where the attacker puts large values in the Byte-Range header   field.  Implementations should sanity-check these values before   allocating memory space for reassembly.   Modification of the ciphertext in EnvelopedData can go undetected if   authentication is not also used, which is the case when sending   EnvelopedData without wrapping it in SignedData or enclosing   SignedData within it.  This is one of the reasons for moving from   EnvelopedData to AuthEnvelopedData, as the authenticated encryption   algorithms provide the authentication without needing the SignedData   layer.   An attack on S/MIME implementations of HTML and multipart/mixed   messages is highlighted in [Efail].  To avoid this attack, clients   MUST ensure that a text/html content type is a complete HTML   document.  Clients SHOULD treat each of the different pieces of the   multipart/mixed construct as coming from different origins.  Clients   MUST treat each encrypted or signed piece of a MIME message as being   from different origins both from unprotected content and from each   other.13.  References13.1.  Normative References   [RFC2119]  Bradner, S., "Key words for use in RFCs to Indicate              Requirement Levels",BCP 14,RFC 2119,              DOI 10.17487/RFC2119, March 1997,              <https://www.rfc-editor.org/info/rfc2119>.   [RFC3261]  Rosenberg, J., Schulzrinne, H., Camarillo, G., Johnston,              A., Peterson, J., Sparks, R., Handley, M., and E.              Schooler, "SIP: Session Initiation Protocol",RFC 3261,              DOI 10.17487/RFC3261, June 2002,              <https://www.rfc-editor.org/info/rfc3261>.   [RFC3264]  Rosenberg, J. and H. Schulzrinne, "An Offer/Answer Model              with Session Description Protocol (SDP)",RFC 3264,              DOI 10.17487/RFC3264, June 2002,              <https://www.rfc-editor.org/info/rfc3264>.Campbell & Housley           Standards Track                   [Page 25]

RFC 8591                S/MIME for SIP Messaging              April 2019   [RFC3428]  Campbell, B., Ed., Rosenberg, J., Schulzrinne, H.,              Huitema, C., and D. Gurle, "Session Initiation Protocol              (SIP) Extension for Instant Messaging",RFC 3428,              DOI 10.17487/RFC3428, December 2002,              <https://www.rfc-editor.org/info/rfc3428>.   [RFC3565]  Schaad, J., "Use of the Advanced Encryption Standard (AES)              Encryption Algorithm in Cryptographic Message Syntax              (CMS)",RFC 3565, DOI 10.17487/RFC3565, July 2003,              <https://www.rfc-editor.org/info/rfc3565>.   [RFC3853]  Peterson, J., "S/MIME Advanced Encryption Standard (AES)              Requirement for the Session Initiation Protocol (SIP)",RFC 3853, DOI 10.17487/RFC3853, July 2004,              <https://www.rfc-editor.org/info/rfc3853>.   [RFC4566]  Handley, M., Jacobson, V., and C. Perkins, "SDP: Session              Description Protocol",RFC 4566, DOI 10.17487/RFC4566,              July 2006, <https://www.rfc-editor.org/info/rfc4566>.   [RFC4975]  Campbell, B., Ed., Mahy, R., Ed., and C. Jennings, Ed.,              "The Message Session Relay Protocol (MSRP)",RFC 4975,              DOI 10.17487/RFC4975, September 2007,              <https://www.rfc-editor.org/info/rfc4975>.   [RFC5084]  Housley, R., "Using AES-CCM and AES-GCM Authenticated              Encryption in the Cryptographic Message Syntax (CMS)",RFC 5084, DOI 10.17487/RFC5084, November 2007,              <https://www.rfc-editor.org/info/rfc5084>.   [RFC5280]  Cooper, D., Santesson, S., Farrell, S., Boeyen, S.,              Housley, R., and W. Polk, "Internet X.509 Public Key              Infrastructure Certificate and Certificate Revocation List              (CRL) Profile",RFC 5280, DOI 10.17487/RFC5280, May 2008,              <https://www.rfc-editor.org/info/rfc5280>.   [RFC5480]  Turner, S., Brown, D., Yiu, K., Housley, R., and T. Polk,              "Elliptic Curve Cryptography Subject Public Key              Information",RFC 5480, DOI 10.17487/RFC5480, March 2009,              <https://www.rfc-editor.org/info/rfc5480>.   [RFC5652]  Housley, R., "Cryptographic Message Syntax (CMS)", STD 70,RFC 5652, DOI 10.17487/RFC5652, September 2009,              <https://www.rfc-editor.org/info/rfc5652>.Campbell & Housley           Standards Track                   [Page 26]

RFC 8591                S/MIME for SIP Messaging              April 2019   [RFC5753]  Turner, S. and D. Brown, "Use of Elliptic Curve              Cryptography (ECC) Algorithms in Cryptographic Message              Syntax (CMS)",RFC 5753, DOI 10.17487/RFC5753, January              2010, <https://www.rfc-editor.org/info/rfc5753>.   [RFC5754]  Turner, S., "Using SHA2 Algorithms with Cryptographic              Message Syntax",RFC 5754, DOI 10.17487/RFC5754, January              2010, <https://www.rfc-editor.org/info/rfc5754>.   [RFC8174]  Leiba, B., "Ambiguity of Uppercase vs Lowercase inRFC2119 Key Words",BCP 14,RFC 8174, DOI 10.17487/RFC8174,              May 2017, <https://www.rfc-editor.org/info/rfc8174>.   [RFC8418]  Housley, R., "Use of the Elliptic Curve Diffie-Hellman Key              Agreement Algorithm with X25519 and X448 in the              Cryptographic Message Syntax (CMS)",RFC 8418,              DOI 10.17487/RFC8418, August 2018,              <https://www.rfc-editor.org/info/rfc8418>.   [RFC8419]  Housley, R., "Use of Edwards-Curve Digital Signature              Algorithm (EdDSA) Signatures in the Cryptographic Message              Syntax (CMS)",RFC 8419, DOI 10.17487/RFC8419, August              2018, <https://www.rfc-editor.org/info/rfc8419>.   [RFC8550]  Schaad, J., Ramsdell, B., and S. Turner, "Secure/              Multipurpose Internet Mail Extensions (S/MIME) Version 4.0              Certificate Handling",RFC 8550, DOI 10.17487/RFC8550,              April 2019, <https://www.rfc-editor.org/info/rfc8550>.   [RFC8551]  Schaad, J., Ramsdell, B., and S. Turner, "Secure/              Multipurpose Internet Mail Extensions (S/MIME) Version 4.0              Message Specification",RFC 8551, DOI 10.17487/RFC8551,              April 2019, <https://www.rfc-editor.org/info/rfc8551>.   [X680]     ITU-T, "Information technology -- Abstract Syntax Notation              One (ASN.1): Specification of basic notation",              ITU-T Recommendation X.680, ISO/IEC 8824-1, August 2015,              <https://www.itu.int/rec/T-REC-X.680>.   [X690]     ITU-T, "Information Technology -- ASN.1 encoding rules:              Specification of Basic Encoding Rules (BER), Canonical              Encoding Rules (CER) and Distinguished Encoding Rules              (DER)", ITU-T Recommendation X.690, ISO/IEC 8825-1, August              2015, <https://www.itu.int/rec/T-REC-X.690/>.Campbell & Housley           Standards Track                   [Page 27]

RFC 8591                S/MIME for SIP Messaging              April 201913.2.  Informative References   [CPM]      Open Mobile Alliance, "OMA Converged IP Messaging System              Description, Candidate Version 2.2", September 2017.   [Efail]    Poddebniak, D., Dresen, C., Muller, J., Ising, F.,              Schinzel, S., Friedberger, S., Somorovsky, J., and J.              Schwenk, "Efail: Breaking S/MIME and OpenPGP Email              Encryption using Exfiltration Channels", August 2018,              <https://www.usenix.org/system/files/conference/usenixsecurity18/sec18-poddebniak.pdf>.   [RCS]      GSMA, "RCS Universal Profile Service Definition Document,              Version 2.2", May 2018,              <https://www.gsma.com/futurenetworks/wp-content/uploads/2018/05/Universal-Profile-RCC.71-v2.2.pdf>.   [RFC3325]  Jennings, C., Peterson, J., and M. Watson, "Private              Extensions to the Session Initiation Protocol (SIP) for              Asserted Identity within Trusted Networks",RFC 3325,              DOI 10.17487/RFC3325, November 2002,              <https://www.rfc-editor.org/info/rfc3325>.   [RFC3840]  Rosenberg, J., Schulzrinne, H., and P. Kyzivat,              "Indicating User Agent Capabilities in the Session              Initiation Protocol (SIP)",RFC 3840,              DOI 10.17487/RFC3840, August 2004,              <https://www.rfc-editor.org/info/rfc3840>.   [RFC3860]  Peterson, J., "Common Profile for Instant Messaging              (CPIM)",RFC 3860, DOI 10.17487/RFC3860, August 2004,              <https://www.rfc-editor.org/info/rfc3860>.   [RFC3862]  Klyne, G. and D. Atkins, "Common Presence and Instant              Messaging (CPIM): Message Format",RFC 3862,              DOI 10.17487/RFC3862, August 2004,              <https://www.rfc-editor.org/info/rfc3862>.   [RFC4648]  Josefsson, S., "The Base16, Base32, and Base64 Data              Encodings",RFC 4648, DOI 10.17487/RFC4648, October 2006,              <https://www.rfc-editor.org/info/rfc4648>.   [RFC4976]  Jennings, C., Mahy, R., and A. Roach, "Relay Extensions              for the Message Sessions Relay Protocol (MSRP)",RFC 4976,              DOI 10.17487/RFC4976, September 2007,              <https://www.rfc-editor.org/info/rfc4976>.Campbell & Housley           Standards Track                   [Page 28]

RFC 8591                S/MIME for SIP Messaging              April 2019   [RFC5438]  Burger, E. and H. Khartabil, "Instant Message Disposition              Notification (IMDN)",RFC 5438, DOI 10.17487/RFC5438,              February 2009, <https://www.rfc-editor.org/info/rfc5438>.   [RFC6121]  Saint-Andre, P., "Extensible Messaging and Presence              Protocol (XMPP): Instant Messaging and Presence",RFC 6121, DOI 10.17487/RFC6121, March 2011,              <https://www.rfc-editor.org/info/rfc6121>.   [RFC7515]  Jones, M., Bradley, J., and N. Sakimura, "JSON Web              Signature (JWS)",RFC 7515, DOI 10.17487/RFC7515, May              2015, <https://www.rfc-editor.org/info/rfc7515>.   [RFC7516]  Jones, M. and J. Hildebrand, "JSON Web Encryption (JWE)",RFC 7516, DOI 10.17487/RFC7516, May 2015,              <https://www.rfc-editor.org/info/rfc7516>.   [RFC7701]  Niemi, A., Garcia-Martin, M., and G. Sandbakken, "Multi-              party Chat Using the Message Session Relay Protocol              (MSRP)",RFC 7701, DOI 10.17487/RFC7701, December 2015,              <https://www.rfc-editor.org/info/rfc7701>.   [RFC7748]  Langley, A., Hamburg, M., and S. Turner, "Elliptic Curves              for Security",RFC 7748, DOI 10.17487/RFC7748, January              2016, <https://www.rfc-editor.org/info/rfc7748>.   [RFC8032]  Josefsson, S. and I. Liusvaara, "Edwards-Curve Digital              Signature Algorithm (EdDSA)",RFC 8032,              DOI 10.17487/RFC8032, January 2017,              <https://www.rfc-editor.org/info/rfc8032>.   [RFC8224]  Peterson, J., Jennings, C., Rescorla, E., and C. Wendt,              "Authenticated Identity Management in the Session              Initiation Protocol (SIP)",RFC 8224,              DOI 10.17487/RFC8224, February 2018,              <https://www.rfc-editor.org/info/rfc8224>.   [RTP-Sec]  Peterson, J., Barnes, R., and R. Housley, "Best Practices              for Securing RTP Media Signaled with SIP", Work in              Progress,draft-ietf-sipbrandy-rtpsec-08, April 2019.Campbell & Housley           Standards Track                   [Page 29]

RFC 8591                S/MIME for SIP Messaging              April 2019Appendix A.  Message Details   The following section shows the detailed content of the S/MIME bodies   used inSection 10.A.1.  Signed Message   Figure 5 shows the details of the message signed by Alice used in the   example inSection 10.1. CMS_ContentInfo:   contentType: pkcs7-signedData (1.2.840.113549.1.7.2)   d.signedData:     version: 1     digestAlgorithms:         algorithm: sha256 (2.16.840.1.101.3.4.2.1)         parameter: <ABSENT>     encapContentInfo:       eContentType: pkcs7-data (1.2.840.113549.1.7.1)       eContent:   0000 - 43 6f 6e 74 65 6e 74 2d-54 79 70 65 3a 20 74   Content-Type: t   000f - 65 78 74 2f 70 6c 61 69-6e 0d 0a 0d 0a 57 61   ext/plain....Wa   001e - 74 73 6f 6e 2c 20 63 6f-6d 65 20 68 65 72 65   tson, come here   002d - 20 2d 20 49 20 77 61 6e-74 20 74 6f 20 73 65    - I want to se   003c - 65 20 79 6f 75 2e 0d 0a-                       e you...     certificates:       d.certificate:         cert_info:           version: 2           serialNumber: 13292724773353297200           signature:             algorithm: ecdsa-with-SHA256 (1.2.840.10045.4.3.2)             parameter: <ABSENT>           issuer: O=example.com, CN=Alice           validity:             notBefore: Dec 19 23:12:05 2017 GMT             notAfter: Dec 19 23:12:05 2018 GMT           subject: O=example.com, CN=Alice           key:             algor:               algorithm: id-ecPublicKey (1.2.840.10045.2.1)               parameter: OBJECT:prime256v1 (1.2.840.10045.3.1.7)             public_key:  (0 unused bits)   0000 - 04 d8 7b 54 72 9f 2c 22-fe eb d9 dd ba 0e   ..{Tr.,"......   000e - fa 40 64 22 97 a6 09 38-87 a4 da e7 99 0b   .@d"...8......   001c - 23 f8 7f a7 ed 99 db 8c-f5 a3 14 f2 ee 64   #............d   002a - 10 6e f1 ed 61 db fc 0a-4b 91 c9 53 cb d0   .n..a...K..S..   0038 - 22 a7 51 b9 14 80 7b b7-94                  ".Q...{..Campbell & Housley           Standards Track                   [Page 30]

RFC 8591                S/MIME for SIP Messaging              April 2019           issuerUID: <ABSENT>           subjectUID: <ABSENT>           extensions:               object: X509v3 Subject Alternative Name (2.5.29.17)               critical: BOOL ABSENT               value:   0000 - 30 17 86 15 73 69 70 3a-61 6c 69 63 65   0...sip:alice   000d - 40 65 78 61 6d 70 6c 65-2e 63 6f 6d      @example.com         sig_alg:           algorithm: ecdsa-with-SHA256 (1.2.840.10045.4.3.2)           parameter: <ABSENT>         signature:  (0 unused bits)   0000 - 30 45 02 20 78 79 be 1c-27 f8 46 27 6f df 15   0E. xy..'.F'o..   000f - e3 33 e5 3c 6f 17 a7 57-38 8a 02 cb 7b 8a e4   .3.<o..W8...{..   001e - 81 c1 64 1a e7 a9 02 21-00 ff 99 cd 9c 94 07   ..d....!.......   002d - 6c 82 b0 2f ea 3b 13 50-17 9a 4b 77 52 e1 6f   l../.;.P..KwR.o   003c - a3 0a 3f 9a b2 96 50 b0-e2 81 89               ..?...P....     crls:       <ABSENT>     signerInfos:         version: 1         d.issuerAndSerialNumber:           issuer: O=example.com, CN=Alice           serialNumber: 13292724773353297200         digestAlgorithm:           algorithm: sha256 (2.16.840.1.101.3.4.2.1)           parameter: <ABSENT>         signedAttrs:             object: contentType (1.2.840.113549.1.9.3)             set:               OBJECT:pkcs7-data (1.2.840.113549.1.7.1)             object: signingTime (1.2.840.113549.1.9.5)             set:               UTCTIME:Jan 24 23:52:56 2019 GMT             object: messageDigest (1.2.840.113549.1.9.4)             set:               OCTET STRING:   0000 - ef 77 8f c9 40 d5 e6 dc-25 76 f4 7a 59   .w..@...%v.zY   000d - 9b 31 26 19 5a 9f 1a 22-7a da f3 5f a2   .1&.Z.."z.._.   001a - 2c 05 0d 8d 19 5a                        ,....Z         signatureAlgorithm:           algorithm: ecdsa-with-SHA256 (1.2.840.10045.4.3.2)           parameter: <ABSENT>Campbell & Housley           Standards Track                   [Page 31]

RFC 8591                S/MIME for SIP Messaging              April 2019         signature:   0000 - 30 45 02 20 58 79 cc 62-85 e0 86 06 19 d3 bf   0E. Xy.b.......   000f - 53 d4 67 9f 03 73 d7 45-20 cf 56 10 c2 55 5b   S.g..s.E .V..U[   001e - 7b ec 61 d4 72 dc 02 21-00 83 aa 53 44 28 4d   {.a.r..!...SD(M   002d - 4c ef de 31 07 9c f9 71-bd 69 5d 6e c8 71 e9   L..1...q.i]n.q.   003c - a4 60 ec 2e 12 65 2b 77-a4 62 4d               .`...e+w.bM         unsignedAttrs:           <ABSENT>                         Figure 5: Signed MessageA.2.  Short Signed Message   Figure 6 shows the message signed by Alice with no embedded   certificate, as used in the example inSection 10.2. CMS_ContentInfo:   contentType: pkcs7-signedData (1.2.840.113549.1.7.2)   d.signedData:     version: 1     digestAlgorithms:         algorithm: sha256 (2.16.840.1.101.3.4.2.1)         parameter: <ABSENT>     encapContentInfo:       eContentType: pkcs7-data (1.2.840.113549.1.7.1)       eContent:   0000 - 43 6f 6e 74 65 6e 74 2d-54 79 70 65 3a 20 74   Content-Type: t   000f - 65 78 74 2f 70 6c 61 69-6e 0d 0a 0d 0a 57 61   ext/plain....Wa   001e - 74 73 6f 6e 2c 20 63 6f-6d 65 20 68 65 72 65   tson, come here   002d - 20 2d 20 49 20 77 61 6e-74 20 74 6f 20 73 65    - I want to se   003c - 65 20 79 6f 75 2e 0d 0a-                       e you...     certificates:       <ABSENT>     crls:       <ABSENT>     signerInfos:         version: 1         d.issuerAndSerialNumber:           issuer: O=example.com, CN=Alice           serialNumber: 13292724773353297200         digestAlgorithm:           algorithm: sha256 (2.16.840.1.101.3.4.2.1)           parameter: <ABSENT>         signedAttrs:             object: contentType (1.2.840.113549.1.9.3)             set:               OBJECT:pkcs7-data (1.2.840.113549.1.7.1)Campbell & Housley           Standards Track                   [Page 32]

RFC 8591                S/MIME for SIP Messaging              April 2019             object: signingTime (1.2.840.113549.1.9.5)             set:               UTCTIME:Jan 24 23:52:56 2019 GMT             object: messageDigest (1.2.840.113549.1.9.4)             set:               OCTET STRING:   0000 - ef 77 8f c9 40 d5 e6 dc-25 76 f4 7a 59   .w..@...%v.zY   000d - 9b 31 26 19 5a 9f 1a 22-7a da f3 5f a2   .1&.Z.."z.._.   001a - 2c 05 0d 8d 19 5a                        ,....Z         signatureAlgorithm:           algorithm: ecdsa-with-SHA256 (1.2.840.10045.4.3.2)           parameter: <ABSENT>         signature:   0000 - 30 44 02 20 1c 51 6e ed-9c 10 10 a2 87 e1 11   0D. .Qn........   000f - 6b af 76 1d f1 c4 e6 48-da ea 17 89 bc e2 8a   k.v....H.......   001e - 9d 8a f4 a4 ae f9 02 20-72 7f 5e 4b cc e2 0b   ....... r.^K...   002d - cf 3c af 07 c8 1c 11 64-f0 21 e7 70 e0 f6 a0   .<.....d.!.p...   003c - 96 2e 0a 7b 19 b7 42 ad-cb 34                  ...{..B..4         unsignedAttrs:           <ABSENT>           Figure 6: Signed Message without Embedded CertificateA.3.  Signed and Encrypted Message   The following sections show details for the message signed by Bob and   encrypted to Alice, as used in the examples in Sections10.3   and 10.4.A.3.1.  Signed Message prior to Encryption CMS_ContentInfo:   contentType: pkcs7-signedData (1.2.840.113549.1.7.2)   d.signedData:     version: 1     digestAlgorithms:         algorithm: sha256 (2.16.840.1.101.3.4.2.1)         parameter: <ABSENT>     encapContentInfo:       eContentType: pkcs7-data (1.2.840.113549.1.7.1)       eContent:   0000 - 43 6f 6e 74 65 6e 74 2d-54 79 70 65 3a 20 74   Content-Type: t   000f - 65 78 74 2f 70 6c 61 69-6e 0d 0a 0d 0a 57 61   ext/plain....Wa   001e - 74 73 6f 6e 2c 20 63 6f-6d 65 20 68 65 72 65   tson, come here   002d - 20 2d 20 49 20 77 61 6e-74 20 74 6f 20 73 65    - I want to se   003c - 65 20 79 6f 75 2e 0d 0a-                       e you...Campbell & Housley           Standards Track                   [Page 33]

RFC 8591                S/MIME for SIP Messaging              April 2019     certificates:       d.certificate:         cert_info:           version: 2           serialNumber: 11914627415941064473           signature:             algorithm: ecdsa-with-SHA256 (1.2.840.10045.4.3.2)             parameter: <ABSENT>           issuer: O=example.org, CN=Bob           validity:             notBefore: Dec 20 23:07:49 2017 GMT             notAfter: Dec 20 23:07:49 2018 GMT           subject: O=example.org, CN=Bob           key:             algor:               algorithm: id-ecPublicKey (1.2.840.10045.2.1)               parameter: OBJECT:prime256v1 (1.2.840.10045.3.1.7)             public_key:  (0 unused bits)   0000 - 04 86 4f ff fc 53 f1 a8-76 ca 69 b1 7e 27   ..O..S..v.i.~'   000e - 48 7a 07 9c 71 52 ae 1b-13 7e 39 3b af 1a   Hz..qR...~9;..   001c - ae bd 12 74 3c 7d 41 43-a2 fd 8a 37 0f 02   ...t<}AC...7..   002a - ba 9d 03 b7 30 1f 1d a6-4e 30 55 94 bb 6f   ....0...N0U..o   0038 - 95 cb 71 fa 48 b6 d0 a3-83                  ..q.H....           issuerUID: <ABSENT>           subjectUID: <ABSENT>           extensions:               object: X509v3 Subject Alternative Name (2.5.29.17)               critical: TRUE               value:   0000 - 30 15 86 13 73 69 70 3a-62 6f 62 40 65   0...sip:bob@e   000d - 78 61 6d 70 6c 65 2e 6f-72 67            xample.org         sig_alg:           algorithm: ecdsa-with-SHA256 (1.2.840.10045.4.3.2)           parameter: <ABSENT>         signature:  (0 unused bits)   0000 - 30 45 02 21 00 b2 24 8c-92 40 28 22 38 9e c9   0E.!..$..@("8..   000f - 25 7f 64 cc fd 10 6f ba-0b 96 c1 19 07 30 34   %.d...o......04   001e - d5 1b 10 2f 73 39 6c 02-20 15 8e b1 51 f0 85   .../s9l. ...Q..   002d - b9 bd 2e 04 cf 27 8f 0d-52 2e 6b b6 fe 4f 36   .....'..R.k..O6   003c - f7 4c 77 10 b1 5a 4f 47-9d e4 0d               .Lw..ZOG...     crls:       <ABSENT>     signerInfos:         version: 1         d.issuerAndSerialNumber:           issuer: O=example.org, CN=Bob           serialNumber: 11914627415941064473Campbell & Housley           Standards Track                   [Page 34]

RFC 8591                S/MIME for SIP Messaging              April 2019         digestAlgorithm:           algorithm: sha256 (2.16.840.1.101.3.4.2.1)           parameter: <ABSENT>         signedAttrs:             object: contentType (1.2.840.113549.1.9.3)             set:               OBJECT:pkcs7-data (1.2.840.113549.1.7.1)             object: signingTime (1.2.840.113549.1.9.5)             set:               UTCTIME:Jan 24 23:52:56 2019 GMT             object: messageDigest (1.2.840.113549.1.9.4)             set:               OCTET STRING:   0000 - ef 77 8f c9 40 d5 e6 dc-25 76 f4 7a 59   .w..@...%v.zY   000d - 9b 31 26 19 5a 9f 1a 22-7a da f3 5f a2   .1&.Z.."z.._.   001a - 2c 05 0d 8d 19 5a                        ,....Z         signatureAlgorithm:           algorithm: ecdsa-with-SHA256 (1.2.840.10045.4.3.2)           parameter: <ABSENT>         signature:   0000 - 30 45 02 21 00 f7 88 ed-44 6a b7 0f ff 2c 1f   0E.!....Dj...,.   000f - fa 4c 03 74 fd 08 77 fd-61 ee 91 7c 31 45 b3   .L.t..w.a..|1E.   001e - 89 a6 76 15 c7 46 fa 02-20 77 94 ad c5 7f 00   ..v..F.. w.....   002d - 61 c7 84 b9 61 23 cc 6e-54 bb 82 82 65 b6 d4   a...a#.nT...e..   003c - cc 12 99 76 a6 b1 fc 6d-bc 28 d6               ...v...m.(.         unsignedAttrs:           <ABSENT>            Figure 7: Message Signed by Bob prior to EncryptionA.3.2.  Encrypted Message CMS_ContentInfo:   contentType: pkcs7-authEnvelopedData (1.2.840.113549.1.9.16.1.23)   d.authEnvelopedData:     version: 0     originatorInfo: <ABSENT>     recipientInfos:       d.ktri:         version: <ABSENT>         d.issuerAndSerialNumber:           issuer: O=example.com, CN=Alice           serialNumber: 9508519069068149774         keyEncryptionAlgorithm:           algorithm: rsaEncryption (1.2.840.113549.1.1.1)           parameter: NULLCampbell & Housley           Standards Track                   [Page 35]

RFC 8591                S/MIME for SIP Messaging              April 2019         encryptedKey:   0000 - 75 9a 61 b4 dd f1 f1 af-24 66 80 05 63 5e 47   u.a.....$f..c^G   000f - 61 10 fa 27 23 c1 b9 e4-54 84 b6 d3 3e 83 87   a..'#...T...>..   001e - de 96 7d c5 e0 ca fb 35-57 1a 56 a1 97 5c b5   ..}....5W.V..\.   002d - 50 e7 be 31 c1 31 da 80-fb 73 10 24 84 5b ab   P..1.1...s.$.[.   003c - b8 d6 4c ac 26 04 04 24-d9 33 05 61 c8 43 99   ..L.&..$.3.a.C.   004b - 94 15 dd 64 4b 3c ad 95-07 2f 71 45 13 93 c9   ...dK<.../qE...   005a - 9f 28 2c 48 83 bd 0c cc-5d d5 4b 93 14 64 e0   .(,H....].K..d.   0069 - 0a 6e 55 e5 92 c5 1a 68-de 10 62 51 6e c7 d3   .nU....h..bQn..   0078 - ca 8e 76 4b b8 ac 78 9a-88 37 77 65 ef 8d c3   ..vK..x..7we...   0087 - 6c 0a 6e d3 ec ae 52 85-ca c6 a2 9d 50 59 44   l.n...R.....PYD   0096 - 57 19 a1 bd cf 90 6e 0f-f3 7e 2c 2e f0 f4 ec   W.....n..~,....   00a5 - 62 25 10 0c c0 62 e1 c7-48 96 3b bc 88 b8 e3   b%...b..H.;....   00b4 - df cf 71 40 73 72 9d d5-c7 58 3e 75 8a cf 3d   ..q@sr...X>u..=   00c3 - 18 6f 2f a4 17 be 22 c3-7c 9a 76 c6 b4 27 29   .o/...".|.v..')   00d2 - aa d2 7f 73 ae 44 ac 98-47 4d 1e eb 48 94 8c   ...s.D..GM..H..   00e1 - 12 a4 03 d0 b3 ce 08 a2-18 d6 af 45 69 24 89   ...........Ei$.   00f0 - 7c c5 c9 66 4f 6d fe b3-f1 81 41 15 8d fc 3b   |..fOm....A...;   00ff - 84 09 0a a6 03 80 aa 86-51 37 e1 69 9c 5c 81   ........Q7.i.\.   010e - 97 41 67 9d 7a 3c 90 ba-79 e6 d7 d5 c8 d8 9b   .Ag.z<..y......   011d - b5 4a 66 74 23 e4 3b 0b-7d 6f 78 c0 b4 ab 67   .Jft#.;.}ox...g   012c - bc 34 36 62 a6 35 fe 59-5f 11 49 c5 39 50 ca   .46b.5.Y_.I.9P.   013b - c2 e0 ba 31 8c 22 7e 6f-76 a8 d9 40 40 0f d3   ...1."~ov..@@..   014a - d3 ea 1c 8e ce a0 03 dc-ce 2f 1f b0 0f 5c ea   ........./...\.   0159 - 33 5d e1 30 3f cb f9 3d-8e 1c bf d6 82 f1 9b   3].0?..=.......   0168 - eb 62 4b ac d1 d7 b8 f5-80 f1 14 a1 3b 89 08   .bK.........;..   0177 - 94 fb 40 44 a5 da a7 64-b7 f8 c5 ff 92 94 94   ..@D...d.......   0186 - 52 b3 5a eb 96 39 b8 ad-63 c0 51 5c 95 cc c6   R.Z..9..c.Q\...   0195 - f8 23 c2 20 10 67 ea 22-62 41 3f ef 39 7d 48   .#. .g."bA?.9}H   01a4 - f7 b6 14 3f 84 2a e8 e1-a4 8c ad 3a e0 1a ba   ...?.*.....:...   01b3 - a3 cf 9e e7 e3 66 20 e0-5c ca 06 11 bf ac 00   .....f .\......   01c2 - ee f1 a4 98 f2 d2 59 b9-f0 f7 da 83 ef 6f 1b   ......Y......o.   01d1 - 06 1f 38 7c 2d c4 8c 8b-5d ba ca 86 23 08 f3   ..8|-...]...#..   01e0 - 2f 47 92 51 65 c9 e5 eb-b4 67 79 98 84 91 8d   /G.Qe....gy....   01ef - d6 97 b4 47 f4 c4 07 98-9b 88 9b 0c 2e 95 80   ...G...........   01fe - af 78                                          .x     authEncryptedContentInfo:       contentType: pkcs7-data (1.2.840.113549.1.7.1)       contentEncryptionAlgorithm:         algorithm: aes-128-gcm (2.16.840.1.101.3.4.1.6)         parameter:           aes-nonce:   0000 - 4d 87 57 22 2e ac 52 94-11 7f 0c 12            M.W"..R.....           aes-ICVlen: 16       encryptedContent:   0000 - fe 2f b3 de 0b f0 69 98-c3 9b f4 a9 52 fa bf   ./....i.....R..   000f - 8b 0f ee 3d 7e 2e 85 18-1a ec f1 a8 9e 1a 2e   ...=~..........   001e - de cd 94 04 88 56 12 df-c6 98 43 34 d8 60 2b   .....V....C4..+Campbell & Housley           Standards Track                   [Page 36]

RFC 8591                S/MIME for SIP Messaging              April 2019   002d - 77 49 b2 50 4e 45 f5 7c-3b 06 66 26 b0 fc 74   wI.PNE.|..f&..t   003c - 62 36 1e ec 26 7c 56 01-39 be 5c d2 86 a2 af   b6..&|V.9.\....   004b - 96 96 cf 51 85 22 78 e5-2c 38 18 ca b0 a6 8c   ...Q."x.,8.....   005a - 59 8d e4 fc e1 4a 33 38-84 e4 de 5d df 57 ed   Y....J38...].W.   0069 - d7 88 67 02 7a 31 e4 a7-c0 c0 29 91 44 c5 de   ..g.z1....).D..   0078 - 6b ae 39 69 9e 70 0e 05-7e b0 f0 da d7 3b 8b   k.9i.p..~......   0087 - 36 9f 42 eb 32 1b 41 53-87 81 d9 82 a1 1a 0b   6.B.2.AS.......   0096 - 39 43 ac 10 c9 7b 54 ee-b7 3b 38 ec 13 1a fc   9C...{T...8....   00a5 - 56 10 e3 73 48 72 74 d6-9c af a9 54 19 02 88   V..sHrt....T...   00b4 - 6c 64 f6 96 2d 42 eb 33-f9 04 1a 4a e1 1b 88   ld..-B.3...J...   00c3 - dc 69 58 d5 3d f5 0b 8b-b5 2a a3 5e 22 99 88   .iX.=....*.^"..   00d2 - 5d 0a ae 41 6b 86 f0 a8-8d 0e b7 a9 81 db b2   ]..Ak..........   00e1 - 83 e8 b9 4e 9d 50 bf 62-65 c2 34 8a 18 a1 69   ...N.P.be.4...i   00f0 - aa cb 5a 37 a5 29 bd a2-f9 cb 10 ef dd cf 14   ..Z7.).........   00ff - 23 10 95 d8 79 64 63 7b-d3 3f b1 3c 68 b4 cf   #...ydc{.?.<h..   010e - f9 a1 90 69 60 c1 ea 23-01 d3 25 b7 a1 5c 58   ...i...#..%..\X   011d - 29 f3 ea 03 8f 24 df 6b-23 18 03 77 d3 71 31   )....$.k#..w.q1   012c - f7 5d b1 8f 41 f9 d8 5b-65 3d fa 46 bf 26 17   .]..A..[e=.F.&.   013b - 12 63 26 cc f1 cb 83 34-57 75 23 52 c8 41 7a   .c&....4Wu#R.Az   014a - 09 44 84 d7 b6 4b cf 51-b2 6a 9b eb 3a 0e d4   .D...K.Q.j..:..   0159 - b9 ca f1 bd 23 c6 90 c6-54 f7 eb 9c e9 85 2e   ....#...T......   0168 - 2f 6d 06 8e ef 8b a3 3b-c6 c4 dd dc a7 ae f4   /m.............   0177 - d3 57 47 37 d7 c4 dc 1e-93 77 0d 8f 4f 22 de   .WG7.....w..O".   0186 - a6 1d 73 08 3c 32 c4 03-8c 1e b3 dd 33 83 a8   ..s.<2......3..   0195 - 9a 87 95 e2 41 c2 ed 7c-b6 80 75 8c 04 10 69   ....A..|..u...i   01a4 - 48 98 60 fc 9f 49 0e 85-23 60 72 54 8b 32 49   H....I..#.rT.2I   01b3 - 69 8f 99 95 3a cf 1e c6-58 b7 aa 85 e5 54 c4   i...:...X....T.   01c2 - 49 70 1a 6d 4b 03 9e d1-03 dc 45 8d f4 b2 9c   Ip.mK.....E....   01d1 - b0 4b 8c ed d5 40 c8 43-48 da 79 c1 86 56 d5   .K...@.CH.y..V.   01e0 - 18 8f 9f 3a 9e 4b 9b 84-0c 70 66 4b 90 29 6c   ...:.K...pfK.)l   01ef - 60 b7 ac 98 4e 91 8d 48-a0 9d bd df b2 81 fc   ....N..H.......   01fe - 86 25 10 db 59 d9 fa 9d-c9 3f 10 f9 c6 d7 be   .%..Y....?.....   020d - f7 29 31 d1 84 ca d7 ac-13 c1 a5 29 5f c8 9f   .)1........)_..   021c - e3 bb 7e b8 e0 20 85 a8-28 c5 a1 38 78 6e 60   ..~.....(..8xn.   022b - 7a de 4f 5e 8d 41 15 90-92 09 ba 87 8a 79 30   z.O^.A.......y0   023a - 5a 53 16 c2 22 29 e4 2b-88 6d 06 48 1c 84 73   ZS..").+.m.H..s   0249 - f9 d5 12 69 e2 af 63 41-bc e2 0f 76 8e 86 0d   ...i..cA...v...   0258 - 77 84 ed 46 15 0e 04 ff-50 cd 20 9c 5b 12 75   w..F....P...[.u   0267 - 11 36 9f e0 6b c4 aa 9a-72 d8 f1 fe 4f cf 08   .6..k...r...O..   0276 - 66 d6 64 b3 65 ff a8 6e-8c 1b 43 e7 a9 21 2a   f.d.e..n..C..!*0285 - ec c1 6c a3 50 a2 8e fa-e2 5f ac 05 4d d9 34   ..l.P...._..M.40294 - bf e7 e5 fa 4f 75 3a a4-15 96 8c 7e be c4 39   ....Ou:....~..9   02a3 - e0 ac 02 70 b4 87 4a 06-8d 22 48 4c 09 d9 e8   ...p..J.."HL...   02b2 - ab e1 7f 13 72 b4 b2 f6-5f 11 48 e8 93 3e da   ....r..._.H..>.   02c1 - 92 e5 d1 77 45 64 96 3b-39 1c 3b bd 9f 1c 27   ...wEd..9......   02d0 - ff e3 6f 83 2e 05 15 5f-c3 9e e6 65 2f a7 b4   ..o...._...e/..   02df - 18 89 75 ec 5c 67 b3 2c-9f 21 3c 8a c6 b8 e1   ..u.\g.,.!<....   02ee - 32 a5 a7 c3 bf 74 f0 16-40 5c d8 c2 01 d1 05   2....t..@\.....Campbell & Housley           Standards Track                   [Page 37]

RFC 8591                S/MIME for SIP Messaging              April 2019   02fd - 21 93 e1 86 d4 43 58 de-38 8d 73 21 1b a2 f1   !....CX.8.s!...   030c - 79 2f 3c fe b9 bb de 72-11 d2 6f 56 ab 06 e1   y/<....r..oV...   031b - 1c cc 9c cd e2 b8 8c d8-37 37 73 ea fc 37 fd   ........77s..7.   032a - 85 b7 a7 a2 bc ae c7 52-e6 17 d6 e0 1c 02 b8   .......R.......   0339 - 6e 9d 9a 40 f3 20 46 2c-5d 66 f8 35 17 16 dc   n..@..F,]f.5...   0348 - d6 01 4b df 30 a6 0f 75-fc 06 31 c9 20 84 5e   ..K.0..u..1...^   0357 - d8 c0 ba d3 5d df 19 84-f2 24 1c d3 b5 29 dc   ....]....$...).   0366 - 10 28 84 5f 80 89 54 3d-f4 f1 44 1e de 36 b1   .(._..T=..D..6.   0375 - bf 31 af 5a fc 8c 2b 70-8d 50 b6 45 d4 e7 db   .1.Z..+p.P.E...   0384 - 88 64 8c 3e ef e1 47 65-15 8f b0 e8 d3 bb 53   .d.>..Ge......S   0393 - dd cb e2 6d 71 24 c6 e1-d9 92 f8 32 30 aa 95   ...mq$.....20..   03a2 - 33 76 ee 8c 68 10 95 68-e8 57 1f 0c 9b bd a4   3v..h..h.W.....   03b1 - 8f 4d f3 06 fe 74 7f 37-11 75 14 8f 31 83 27   .M...t.7.u..1..   03c0 - 67 cd 76 6c f0 7b 45 0c-bf 62 ca d2 a7 bd 71   g.vl.{E..b....q   03cf - f1 f8 82 33 f1 16 a1 a7-f3 ca f1 2f 34 bc f4   ...3......./4..   03de - 0d 21 e7 9f fc 98 27 22-1b 68 b0 80 ff 03 ad   .!.....".h.....   03ed - 78 2d 6d 6d 07 87 16 76-f7 98 94 3e 54 f1 3f   x-mm...v...>T.?   03fc - d7 5c 89 c0 b4 26 3b f1-0f 56 24 3f 9e 72 ef   .\...&...V$?.r.   040b - 3b 38 99 a5 39 d9 a3 ac-5b e2 b6 94 00 a3 cf   .8..9...[......   041a - 8d 19 6c 5c ed 69 7b 2e-d8 03 b9 87 a5 ee 85   ..l\.i{........   0429 - c5 09 5b 48 da 7a 5b 03-b4 7e 2b 9f e4 cd 4b   ..[H.z[..~+...K   0438 - c3 09 8e 86 4e 0c e7 d4-67 da 99 cd 7f 3a 9e   ....N...g....:.   0447 - 94 7b 5e ea 77 f7 a6 be-16 c8 c7 e9 e0 de cc   .{^.w..........   0456 - 1f f1 32 55 9c 23 43 21-7b 9c 29 50 38 6e 85   ..2U.#C!{.)P8n.   0465 - d2 94 21 21 08 6c df a1-96 58 19 5b e6 d7 f8   ..!!.l...X.[...   0474 - 6b ca 98 81 b6 95 08 29-64 f1 2e 7c f8 01 02   k......)d..|...   0483 - 5d 67 92 c6 88 24 09 41-4d 70 33 21 ec 83 ab   ]g...$.AMp3!...   0492 - d6 98 d6 89 56 11 87 13-a0 ff 12 72 ac bc 9a   ....V......r...   04a1 - 6d 14 89 00 c7 4c 16 92-1d f9 b3 8f 29 ec 46   m....L......).F   04b0 - d4 f1 00 60 ff fe 5e 36-bb ba ca f2 d1 ba d7   ......^6.......   04bf - dd 05 7e d3 e3 0e bc d6-90 83 f9 d3 a2 a2 6e   ..~...........n   04ce - f9 0b 75 1d 6a 1a df a0-59 0d b1 9d a1 07 cf   ..u.j...Y......   04dd - 3e a8 db                                       >..     authAttrs:       <EMPTY>     mac:0000 - f6 ff c6 e1 ae f1 9c d2-3d 98 5a 92 19 76 35   ........=.Z..v5   000f - 2d                                             -     unauthAttrs:       <EMPTY>               Figure 8: Message Encrypted by Bob for AliceCampbell & Housley           Standards Track                   [Page 38]

RFC 8591                S/MIME for SIP Messaging              April 2019Authors' Addresses   Ben Campbell   Standard Velocity, LLC   Email: ben@nostrum.com   Russ Housley   Vigil Security, LLC   Email: housley@vigilsec.comCampbell & Housley           Standards Track                   [Page 39]

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