Network Working Group                                         R. Gellens
Request for Comments: 5383                                      Qualcomm
BCP: 143                                                    October 2008
Category: Best Current Practice

     Deployment Considerations for Lemonade-Compliant Mobile Email

Status of This Memo

   This document specifies an Internet Best Current Practices for the
   Internet Community, and requests discussion and suggestions for
   improvements.  Distribution of this memo is unlimited.


   This document discusses deployment issues and describes requirements
   for successful deployment of mobile email that are implicit in the
   IETF lemonade documents.

Table of Contents

   1. Introduction ....................................................2
   2. Conventions Used in This Document ...............................2
   3. Ports ...........................................................2
   4. TCP Connections .................................................3
      4.1. Lifetime ...................................................4
      4.2. Maintenance during Temporary Transport Loss ................5
   5. Dormancy ........................................................6
   6. Firewalls .......................................................6
      6.1. Firewall Traversal .........................................7
   7. NATs ............................................................8
   8. Security Considerations .........................................8
   9. Acknowledgments ................................................10
   10. Normative References ..........................................10
   11. Informative References ........................................10

Gellens                  Best Current Practice                  [Page 1]

RFC 5383           Lemonade Deployment Considerations       October 2008

1.  Introduction

   The IETF lemonade group has developed a set of extensions to IMAP and
   Message Submission, along with a profile document that restricts
   server behavior and describes client usage [PROFILE].

   Successful deployment of lemonade-compliant mobile email requires
   various functionality that is generally assumed and hence not often
   covered in email RFCs.  This document describes some of these
   additional considerations, with a focus on those that have been
   reported to be problematic.

2.  Conventions Used in This Document

   The key words "MUST", "MUST NOT", "REQUIRED", "SHALL", "SHALL NOT",
   document are to be interpreted as described in [KEYWORDS].

3.  Ports

   Both IMAP and Message Submission have been assigned well-known ports
   [IANA] that MUST be available.  IMAP uses port 143.  Message
   Submission uses port 587.  It is REQUIRED that the client be able to
   contact the server on these ports.  Hence, the client and server
   systems, as well as any intermediary systems, MUST allow
   communication on these ports.

   Historically, Message User Agents (MUAs) have used port 25 for
   Message Submission, and [SUBMISSION] does accommodate this.  However,
   it has become increasingly common for ISPs and organizations to
   restrict outbound port 25.  Additionally, hotels and other public
   accommodations sometimes intercept port 25 connections, regardless of
   the destination host, resulting in users unexpectedly submitting
   potentially sensitive communications to unknown and untrusted third-
   party servers.  Typically, users are not aware of such interception.
   (Such interception violates [FIREWALLS] and has many negative

   Due to endemic security vulnerabilities in widely deployed SMTP
   servers, organizations often employ application-level firewalls that
   intercept SMTP and permit only a limited subset of the protocol.  New
   extensions are therefore more difficult to deploy on port 25.  Since
   lemonade requires support for several [SUBMISSION] extensions, it is
   extremely important that lemonade clients use, and lemonade servers
   listen on, port 587 by default.

Gellens                  Best Current Practice                  [Page 2]

RFC 5383           Lemonade Deployment Considerations       October 2008

   In addition to communications between the client and server systems,
   lemonade requires that the Message Submission server be able to
   establish a TCP connection to the IMAP server (for forward-without-
   download).  This uses port 143 by default.

   Messaging clients sometimes use protocols to store, retrieve, and
   update configuration and preference data.  Functionality such as
   setting a new device to use the configuration and preference data of
   another device, or having a device inherit default configuration data
   from a user account, an organization, or other source, is likely to
   be even more useful with small mobile devices.  Various protocols can
   be used for configuration and preference data; most of these
   protocols have designated ports.  It is important that clients be
   able to contact such servers on the appropriate ports.  As an
   example, one protocol that can be used for this purpose is [ACAP], in
   which case port 674 needs to be available.

   Note that systems that do not support application use of [TCP] on
   arbitrary ports are not full Internet clients.  As a result, such
   systems use gateways to the Internet that necessarily result in data
   integrity problems.

4.  TCP Connections

   Both IMAP and Message Submission use [TCP].  Hence, the client system
   MUST be able to establish and maintain TCP connections to these
   servers.  The Message Submission server MUST be able to initiate a
   connection to the IMAP server.  Support for application use of [TCP]
   is REQUIRED of both client and server systems.

   The requirements and advice in [HOST-REQUIREMENTS] SHOULD be

   Note that, for environments that do not support application use of
   [TCP] but do so for HTTP, email can be offered by deploying webmail.
   Webmail is a common term for email over the web, where a server
   speaks HTTP to the client and an email protocol (often IMAP) to the
   mail store.  Its functionality is necessarily limited by the
   capabilities of the web client, the webmail server, the protocols
   used between the webmail server and the client (HTTP and a markup
   language such as HTML), and between the webmail server and the mail
   store.  However, if HTTP is all that is available to an application,
   the environment is by definition limited and thus, functionality
   offered to the user must also be limited, and can't be lemonade

Gellens                  Best Current Practice                  [Page 3]

RFC 5383           Lemonade Deployment Considerations       October 2008

4.1.  Lifetime

   In this document, "idle" refers to the idle time, as in the
   "established connection idle-timeout" of [BEHAVE-TCP], while
   "duration" refers to the total time that a TCP connection has been

   The duration of the TCP connections between the client and server
   systems for both IMAP and Message Submission can be arbitrarily long.
   The client system, the server, as well as all intermediate systems
   MUST NOT terminate these TCP connections simply because of their
   duration (that is, just because of how long they have been open).

   Lemonade depends on idle timers being enforced only at the
   application level (IMAP and Message Submission): if no data is
   received within a period of time, either side MAY terminate the
   connection as permitted by the protocol (see [SUBMISSION] or [IMAP]).
   Since IMAP permits unsolicited notifications of state changes, it is
   reasonable for clients to remain connected for extended periods with
   no data being exchanged.  Being forced to send data just to keep the
   connection alive can prevent or hinder optimizations such as dormancy
   mode (see Section 5).

   Two hours is a fairly common configuration timeout at middleboxes.
   That is, there are a number of sites at which TCP connections are
   torn down by the network two hours after data was last sent in either
   direction (for example, REQ-5 in [BEHAVE-TCP]).  Thus, lemonade
   clients and servers SHOULD make sure that, in the absence of a
   specific configuration setting that specifies a longer maximum idle
   interval, the TCP connection does not remain idle for two hours.
   This rule ensures that, by default, lemonade clients and servers
   operate in environments configured with a two-hour maximum for idle
   TCP connections.  Network and server operators can still permit IMAP
   connections to remain idle in excess of two hours and thus increase
   the benefits of dormancy, by configuring lemonade clients and
   servers, and network equipment, to allow this.

   It has been reported that some networks impose duration time
   restrictions of their own on TCP connections other than HTTP.  Such
   behavior is harmful to email and all other TCP-based protocols.  It
   is unclear how widespread such reported behavior is, or if it is an
   accidental consequence of an attempt at optimizing for HTTP traffic,
   implementation limitations in firewalls, NATs, or other devices, or a
   deliberate choice.  In any case, such a barrier to TCP connections is
   a significant risk to the increasing usage of IETF protocols on such
   networks.  Note that TCP is designed to be more efficient when it is

Gellens                  Best Current Practice                  [Page 4]

RFC 5383           Lemonade Deployment Considerations       October 2008

   used to transfer data over time.  Prohibiting such connections thus
   imposes hidden costs on an operator's network, forcing clients to use
   TCP in inefficient ways.  One way in which carriers can inadvertently
   force TCP connections closed, resulting in users wasting packets by
   reopening them, is described in Section 7.

   Note that systems remain able to terminate TCP connections at any
   time based on local decisions, for example, to prevent overload
   during a denial-of-service attack.  These mechanisms are permitted to
   take idle time into consideration and are not affected by these

4.2.  Maintenance during Temporary Transport Loss

   TCP is designed to withstand temporary loss of lower-level
   connectivity.  Such transient loss is not uncommon in mobile systems
   (for example, due to handoffs, fade, etc.).  The TCP connection
   SHOULD be able to survive temporary lower-level loss when the IP
   address of the client does not change (for example, short-duration
   loss of the mobile device's traffic channel or periods of high packet
   loss).  Thus, the TCP/IP stack on the client, the server, and all
   intermediate systems SHOULD maintain the TCP connection during
   transient loss of connectivity.

   In general, applications can choose whether or not to enable TCP
   keep-alives, but in many cases are unable to affect any other aspect
   of TCP keep-alive operation, such as time between keep-alive packets,
   number of packets sent before the connection is aborted, etc.  In
   some environments, these are operating system tuning parameters not
   under application control.  In some cases, operational difficulties
   have been reported with application use of the TCP keep-alive option,
   which might be the result of TCP implementation differences or
   defects specific to a platform.  Lemonade client and server systems
   SHOULD NOT set the TCP keep-alive socket option unless operating in
   environments where this works correctly and such packets will not be
   sent more frequently than every two hours.  Application-level keep-
   alives (such as IMAP NOOP) MAY be used instead of the TCP keep-alive

   Client, server, and intermediate systems MUST comply with the
   "Destination Unreachable -- codes 0, 1, 5" text in Section of
   [HOST-REQUIREMENTS], which states "Since these Unreachable messages
   indicate soft error conditions, TCP MUST NOT abort the connection".

Gellens                  Best Current Practice                  [Page 5]

RFC 5383           Lemonade Deployment Considerations       October 2008

5.  Dormancy

   Cellular data channels are connection-oriented (they are brought up
   or down to establish or tear down connections); it costs network
   resources to establish connections.  Generally speaking, mobile
   device battery charges last longer when the traffic channel is used

   Some mobile devices and networks support dormant mode, in which the
   traffic channel is brought down during idle periods, yet the PPP or
   equivalent level remains active, and the mobile retains its IP

   Maintenance of TCP connections during dormancy SHOULD be supported by
   the client, server, and any intermediate systems, as described in
   Sections 4.1 and 4.2.

   Sending packets just to keep the session active causes unnecessary
   channel establishment and timeout; with a long-idle TCP connection,
   this would periodically bring up the channel and then let it idle
   until it times out, again and again.  However, in the absence of
   specific configuration information to the contrary, it is necessary
   to do this to ensure correct operation by default.

6.  Firewalls

   New services must necessarily have their traffic pass through
   firewalls in order to be usable by corporate employees or
   organization members connecting externally, such as when using mobile
   devices.  Firewalls exist to block traffic, yet exceptions must be
   made for services to be used.  There is a body of best practices
   based on long experience in this area.  Numerous techniques exist to
   help organizations balance protecting themselves and providing
   services to their members, employees, and/or customers. (Describing,
   or even enumerating, such techniques and practices is beyond the
   scope of this document, but Section 8 does mention some.)

   It is critical that protocol design and architecture permit such
   practices, and not constrain them.  One key way in which the design
   of a new service can aid its secure deployment is to maintain the
   one-to-one association of services and port numbers.

Gellens                  Best Current Practice                  [Page 6]

RFC 5383           Lemonade Deployment Considerations       October 2008

   One or more firewalls might exist in the path between the client and
   server systems, as well as between the Message Submission and IMAP
   servers.  Proper deployment REQUIRES that TCP connections be possible
   from the client system to the IMAP and Message Submission ports on
   the servers, as well as from the Message Submission server to the
   IMAP server.  This may require configuring firewalls to permit such

   Firewalls deployed in the network path MUST NOT damage protocol
   traffic.  In particular, both Message Submission and IMAP connections
   from the client MUST be permitted.  Firewalls MUST NOT partially
   block extensions to these protocols, such as by allowing one side of
   an extension negotiation, as doing so results in the two sides being
   out of synch, with later failures.  See [FIREWALLS] for more

   Application proxies, which are not uncommon mechanisms, are discussed
   in [PROXIES].

6.1.  Firewall Traversal

   An often-heard complaint from those attempting to deploy new services
   within an organization is that the group responsible for maintaining
   the firewall is unable or unwilling to open the required ports.  The
   group that owns the firewall, being charged with organizational
   network security, is often reluctant to open firewall ports without
   an understanding of the benefits and the security implications of the
   new service.

   The group wishing to deploy a new service is often tempted to bypass
   the procedure and internal politics necessary to open the firewall
   ports.  A tempting kludge is to tunnel the new service over an
   existing service that is already permitted to pass through the
   firewall, typically HTTP on port 80 or sometimes SMTP on port 25.
   Some of the downsides to this are discussed in [KLUDGE].

   Such a bypass can appear to be immediately successful, since the new
   service seems to deploy.  However, assuming the network security
   group is competent, when they become aware of the kludge, their
   response is generally to block the violation of organizational
   security policy.  It is difficult to design an application-level
   proxy/firewall that can provide such access control without violating
   the transparency requirements of firewalls, as described in
   [FIREWALLS].  Collateral damage is common in these circumstances.
   The new service (which initially appeared to have been successfully
   deployed) as well as those existing services that were leveraged to
   tunnel the new service, become subject to arbitrary and unpredictable

Gellens                  Best Current Practice                  [Page 7]

RFC 5383           Lemonade Deployment Considerations       October 2008

   failures.  This encourages an adversarial relationship between the
   two groups, which hinders attempts at resolution.

   Even more serious is what happens if a vulnerability is discovered in
   the new service.  Until the vulnerability is corrected, the network
   security group must disable both the new service and the (typically
   mission-critical) existing service on which it is layered.

   An often-repeated truism is that any computer that is connected to a
   network is insecure.  Security and usefulness are both
   considerations, with organizations making choices about achieving
   acceptable measures in both areas.  Deploying new services typically
   requires deciding to permit access to the ports used by the service,
   with appropriate protections.  While the delay necessary to review
   the implications of a new service may be frustrating, in the long
   run, it is likely to be less expensive than a kludge.

7.  NATs

   Any NAT boxes that are deployed between client and server systems
   MUST comply with REQ-5 in [BEHAVE-TCP], which requires that "the
   value of the 'established connection idle-timeout' MUST NOT be less
   than 2 hours 4 minutes".

   See Section 5 for additional information on connection lifetimes.

   Note that IMAP and Message Submission clients will automatically re-
   open TCP connections as needed, but it saves time, packets, and
   processing to avoid the need to do so.  Re-opening IMAP and Message
   Submission connections generally incurs costs for authentication,
   Transport Layer Security (TLS) negotiation, and server processing, as
   well as resetting of TCP behavior, such as windows.  It is also
   wasteful to force clients to send NOOP commands just to maintain NAT
   state, especially since this can defeat dormancy mode.

8.  Security Considerations

   There are numerous security considerations whenever an organization
   chooses to make any of its services available via the Internet.  This
   includes email from mobile clients.

   Sites concerned about email security should perform a threat
   analysis, get relevant protections in place, and then make a
   conscious decision to open up this service.  As discussed in Section
   6.1, piggybacking email traffic on the HTTP port in an attempt to
   avoid making a firewall configuration change to explicitly permit
   mobile email connections would bypass this important step and reduce
   the overall security of the system.

Gellens                  Best Current Practice                  [Page 8]

RFC 5383           Lemonade Deployment Considerations       October 2008

   Organizations deploying a messaging server "on the edge" (that is,
   accessible from the open Internet) are encouraged to choose one that
   has been designed to operate in that environment.

   This document does not attempt to catalogue either the various risks
   an organization might face or the numerous techniques that can be
   used to protect against the risks.  However, to help illustrate the
   deployment considerations, a very small sample of some of the risks
   and countermeasures appear below.

   Some organizations are concerned that permitting direct access to
   their mail servers via the Internet increases their vulnerability,
   since a successful exploit against a mail server can potentially
   expose all mail and authentication credentials stored on that server,
   and can serve as an injection point for spam.  In addition, there are
   concerns over eavesdropping or modification of mail data and
   authentication credentials.

   A large number of approaches exist that can mitigate the risks while
   allowing access to mail services via mobile clients.

   Placing servers inside one or more DMZs (demilitarized zones, also
   called perimeter networks) can protect the rest of the network from a
   compromised server.  An additional way to reduce the risk is to store
   authentication credentials on a system that is not accessible from
   the Internet and that the servers within the DMZ can access only by
   sending the credentials as received from the client and receiving an
   authorized/not authorized response.  Such isolation reduces the
   ability of a compromised server to serve as a base for attacking
   other network hosts.

   Many additional techniques for further isolation exist, such as
   having the DMZ IMAP server have no mail store of its own.  When a
   client connects to such a server, the DMZ IMAP server might contact
   the authentication server and receive a ticket, which it passes to
   the mail store in order to access the client's mail.  In this way, a
   compromised IMAP server cannot be used to access the mail or
   credentials for other users.

   It is important to realize that simply throwing an extra box in front
   of the mail servers, such as a gateway that may use HTTP or any of a
   number of synchronization protocols to communicate with clients, does
   not itself change the security aspects.  By adding such a gateway,
   the overall security of the system, and the vulnerability of the mail
   servers, may remain unchanged or may be significantly worsened.
   Isolation and indirection can be used to protect against specific
   risks, but to be effective, such steps need to be done after a threat
   analysis, and with an understanding of the issues involved.

Gellens                  Best Current Practice                  [Page 9]

RFC 5383           Lemonade Deployment Considerations       October 2008

   Organizations SHOULD deploy servers that support the use of TLS for
   all connections and that can be optionally configured to require TLS.
   When TLS is used, it SHOULD be via the STARTTLS extensions rather
   than the alternate port method.  TLS can be an effective measure to
   protect against specific threats, including eavesdropping and
   alteration, of the traffic between the endpoints.  However, just
   because TLS is deployed does not mean the system is "secure".

   Attempts at bypassing current firewall policy when deploying new
   services have serious risks, as discussed in Section 6.1.

   It's rare for a new service to not have associated security
   considerations.  Making email available to an organization's members
   using mobile devices can offer significant benefits.

9.  Acknowledgments

   Chris Newman and Phil Karn suggested very helpful text.  Brian Ross
   and Dave Cridland reviewed drafts and provided excellent suggestions.

10.  Normative References

   [BEHAVE-TCP]        Guha, S., Ed., Biswas, K., Ford, B., Sivakumar,
                       S., and P. Srisuresh, "NAT Behavioral
                       Requirements for TCP", BCP 142, RFC 5382, October

   [HOST-REQUIREMENTS] Braden, R., Ed., "Requirements for Internet Hosts
                       - Communication Layers", STD 3, RFC 1122, October

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

   [IANA]              IANA Port Number Registry,

   [TCP]               Postel, J., "Transmission Control Protocol", STD
                       7, RFC 793, September 1981.

11.  Informative References

   [ACAP]              Newman, C. and J. Myers, "ACAP -- Application
                       Configuration Access Protocol", RFC 2244,
                       November 1997.

Gellens                  Best Current Practice                 [Page 10]

RFC 5383           Lemonade Deployment Considerations       October 2008

   [FIREWALLS]         Freed, N., "Behavior of and Requirements for
                       Internet Firewalls", RFC 2979, October 2000.

   [IMAP]              Crispin, M., "INTERNET MESSAGE ACCESS PROTOCOL -
                       VERSION 4rev1", RFC 3501, March 2003.

   [KLUDGE]            Moore, K., "On the use of HTTP as a Substrate",
                       BCP 56, RFC 3205, February 2002.

   [PROFILE]           Maes, S. and A. Melnikov, "Internet Email to
                       Support Diverse Service Environments (Lemonade)
                       Profile", RFC 4550, June 2006.

   [PROXIES]           Chatel, M., "Classical versus Transparent IP
                       Proxies", RFC 1919, March 1996.

   [SUBMISSION]        Gellens, R. and J. Klensin, "Message Submission
                       for Mail", RFC 4409, April 2006.

Author's Address

   Randall Gellens
   QUALCOMM Incorporated
   5775 Morehouse Drive
   San Diego, CA  92121


Gellens                  Best Current Practice                 [Page 11]

RFC 5383           Lemonade Deployment Considerations       October 2008

Full Copyright Statement

   Copyright (C) The IETF Trust (2008).

   This document is subject to the rights, licenses and restrictions
   contained in BCP 78, and except as set forth therein, the authors
   retain all their rights.

   This document and the information contained herein are provided on an

Intellectual Property

   The IETF takes no position regarding the validity or scope of any
   Intellectual Property Rights or other rights that might be claimed to
   pertain to the implementation or use of the technology described in
   this document or the extent to which any license under such rights
   might or might not be available; nor does it represent that it has
   made any independent effort to identify any such rights.  Information
   on the procedures with respect to rights in RFC documents can be
   found in BCP 78 and BCP 79.

   Copies of IPR disclosures made to the IETF Secretariat and any
   assurances of licenses to be made available, or the result of an
   attempt made to obtain a general license or permission for the use of
   such proprietary rights by implementers or users of this
   specification can be obtained from the IETF on-line IPR repository at

   The IETF invites any interested party to bring to its attention any
   copyrights, patents or patent applications, or other proprietary
   rights that may cover technology that may be required to implement
   this standard.  Please address the information to the IETF at

Gellens                  Best Current Practice                 [Page 12]