Rohit Khare (
Thu, 10 Sep 1998 19:30:48 -0700

The Spec's in the Mail

Rohit Khare // September 1, 1998

"It's made of people!"

While the surface intent of the ARPANET was serious experimentation
with computer-to-computer communication, the secret ingredient in its
success was the same as in Soylent Green: people. Electronic mail (ne
'netmail') and, later, news were the twin killer apps that motivated
many institutions to join regional networks, and later, to
internetwork them. Human collaboration turned out to be more
compelling than such digital dreams as an automated Data
Reconfiguration Service (RFC 194) or unified binary encoding (RFC 31)
or a programmable Network Standard Translator (RFC 5).

Peter Salus' oral history, Casting the Net (Addison-Wesley, 1995) goes
so far as to deem network e-mail "the application that hadn't been
thought of." Just because chit-chat was an afterthought to the Real
Work of timesharing and file transfer and distributed processing
doesn't mean modern protocol designers can skim past it, though.
E-mail is the "missing link" in the evolutionary lineage from
interactive control protocols like Telnet and FTP to modern
message-transfer systems like HTTP and NNTP. And since ontogeny
recapitulates phylogeny in this case, application-layer designers can
reflect upon how the mail-relay infrastructure to route text and
multimedia "packets" rediscovered classic IP-layer solutions to
fragmentation, congestion, error propagation, security, and other

This installment of Seventh Heaven focuses on the coevolution of the
Internet Text Message (RFC 822) format and the Simple Mail Transfer
Protocol (SMTP, RFC 821), from its roots as a printer-spooling
convention piggybacked on File Transfer Protocol (FTP) through the
development of the Multipurpose Internet Mail Extensions (MIME) up to
the latest drafts of the Detailed Revision/Update of Message Standards
(DRUMS) working group.

Babel, Tower of: see 'Mail Box Protocol'

Virtually every multiuser computer installation has had a user-user
messaging and/or paging facility, right back to the original maliboxes
in the Compatible Time Sharing System (CTSS) of the early 60's. The
operative metaphor for wide-area text messaging already existed, too:
public Telex service promised (relatively) low-latency guaranteed
delivery around the world (or so I'm told, having grown up in the Fax
Age -- I've never seen a telegram or telex in real life!). Electronic
mail across the ARPANET, like terminal emulation and file transfer
before it, was merely a simple matter of virtualizing the diversity of
hosts, terminals, printers, and user identification schemes out there.

In that spirit, Richard Watson's modest proposal for a "Mail Box
Protocol" (RFC 196) is best understood as a remote, deferred printer
service. Inspired by primitive TELNET, it added one control code
selects the 7-bit mailbox number; 0 is reserved for the "system
printer," with its own control codes for character set (ASCII, EBCDIC,
or 8-bit stream), page length (66 lines or infinite) and width (72
characters or max). Other mailboxes' formats were undefined, since he
noted "it is useful to have more than one receiving mail box, each to
be associated with a different process."

The only recognizable user identifier is an optional burst page: "This
address string is to contain the sender's name and address, and the
receiver's name and address formatted in some reasonable, easy-to-read
form for a clerk to read and distribute." RFC 278's later revisions
strengthened it to a requirement: "At the head of the message or
document sent there is to be two copies of an initial address string
each terminated by a form feed... make one readable from a fan fold
paper stack without effort."

RFC 278 reconstructed e-mail as an application of file transfer. It
reserves a top-level MAIL directory, containing files for each user
and the PRINTER. Messages were delivered using Append With Create
(command 5, before the advent of text protocols). It required
end-to-end connectivity: one connected directly to the target machine
to send mail. Addressing was centralized, with the Network Information
Center (NIC) maintaining identifiers and group mailboxes to burst RFCs
and operation memos to each ARPANET site -- and they liked it that
way: their oNLine System (NLS) could store and search every piece of

Even though e-mail in 1971 lacked effective abstractions for
addressing, distribution, and content -- the hallmarks of a TP
(transfer protocol) -- the future was visible. RFC 224 commented that
the "printer" model was already obsolete. Alex McKenzie predicted that
"a message destined for a Terminal IMP user would be shipped to the
site of the 'rented' mailbox according to protocol and stored there. A
terminal IMP user could then periodically log in to that site (under
TELNET protocol) and examine the contents of the mailbox"

Throughout the Seventies, a flurry of mail systems tinkered around the
edges: reserving "secure" ports, decentralizing addresses around the
'@' fulcrum, avoiding junk mail, and creating new message headings.
RFC 808's survey of 36 mailers circa January 1979 noted "most of the
mail systems were not formal projects (in the sense of explicitly
sponsored research), but things that 'just happened'." Real change
would have to wait until the transition from NCP to TCP in the early
Eighties: as the October 1980 plan (RFC 773) recalled, "In the
ARPANET, electronic messages are transported via special procedures of
the File Transfer Protocol: MAIL and MLFL. The former method sends
electronic messages via the FTP Telnet command channel while the
latter achieves this by actual file transfer."

Once the prospect of internetwork e-mail was raised, the real work
began: fresh solutions to each of the three aspects of a Message
Transfer Protocol: Addressing, Distribution, and Content --
culminating in RFCs 974, 821, and 822, respectively.


E-mail's line-printer origins still constrain its content model thirty
years later. The key to understanding the arcana and fuzziness of
e-mail format wars is an unspoken assumption that the most primitive
user interface to mail is a still a printout -- and thus has to make
sense to a human.

Header fields are our basic building block: simultaneously human- and
machine-readable, they appear in a clump at the beginning of a memo,
followed by a single blank line. And helpfully suggestive names like
"Date:" and "From:," are ripe for misinterpretation, igniting jihads
of all sorts. The header-people discussion list from this era --
probably the first e-mail mediated virtual community -- reveals this
tendency in spades (@@URL of archive@@).

New headers require new grammars, usually assembled from the suite of
parsing rules in RFC822, and now IETF's official Augmented Bakus-Naur
Form notation (RFC 2234). Those already specify how to fold headers
across multiple lines (80-column printers strike again!), escape
reserved characters, and basic values like Message-ID.

The struggle for interoperabilty in the real world requires
accomodating buggy variants thereof, too. The maxim "Be conservative
in what you generate and liberal in what you accept" arose in this
context -- but within limits. Liberalism lets bad specifications live
on (like 822's 2-digit years), and worse yet, fast-and-loose
implementations that force other upstanding members of the mail relay
community to clean up their messes.

Such flexibility is essential to e-mail's evolvability: even the most
basic parsers can still grok the latest whiz-bang video mail because
of MIME's judicious use of headers, 7-bit clean bodies, and
line-length limits. It introduced the notion of content type and
message parts, allowing more sophisticated systems to look at the same
message and extract a structured tree of resources, and to understand
how to present each resource.

As intended, most new email applications need only define new
content-types for encryption, digital signatures, Electronic Data
Interchange (EDI), or Web page delivery. Internet Media Types are
registered in a two-level hierarchy that implies interchangeability
under each primary type (e.g. text/*, image/*, video/*). Political
control of this namespace has been contentious around the edges,
especially for proprietary types. Ironically, the Web's fateful
adoption of the same will ensure its survival, but that's a tale for
another column...

If you have to call it 'Simple'...

IP packets can drop with impunity, but email never should. Reliable
delivery requires clients to retry delivery until positive
acknowledgement, and server to ensure stable storage of the message
before acknowledgement -- leaving a race condition if the connection
drops in between leading to duplicate delivery (RFC 1047). Clients
will also keep retrying delivery to a machine without email service,
like a DNS server (RFC 1846). Message length shouldn't be restricted
by the protocol, but if there's a constrained server in the path,
there has to be an entire size-discovery method (RFC 1653). All of
these nits with reliable end-to-end delivery across the Internet --
including queuing for intermittently connected hosts -- still pale by
comparison to the challenges of gatewaying mail to other network
architectures (X.400 mappings are standardized in RFCs 2156-7).

By the time of the Great Transition to TCP, e-mail had grown into a
series of hacks on top of FTP. Naturally, the first cut at a Mail
Transfer Protocol (MTP) mimicked those very commands: "MAIL TO: <>
FROM: <>", with optional support for additional recipients, to be
listed before or after the mail body. Simplification actually
separated out more states: SMTP commands for creating a new mail
message, verifying addresses and expanding lists, adding recipients,
then sending the body -- and each with their own reply codes,
affording much more accurate debugging.

A decade later, ESMTP was deemed the new standard, with its EHLO
greeting that advertised available extensions. New functionality could
be registered under a keyword and could add new parameters to existing
commands. Its maxim was: "protocols with few options tend towards
ubiquity, whilst protocols with many options tend towards obscurity."
Extensions standardized to date provide important functionality:
transmitting large and 8-bit bodies (RFC 1830), limiting message size
(RFC 1870), requesting delivery status notification (RFC 1891),
initiating a destination's queued mail delivery (RFC 1985), using more
specific reply codes (RFC 2034), and pipelining commands (RFC 2157).

Poste Restante

The Great Transition also required e-mail addressing to adapt to the
newfangled Domain Naming System (DNS). The Internet had grown well
past the point that mail relays could directly connect to destination
servers; intranets (had the term existed) had also grown too large to
host users' mail at individual hosts. Instead of requiring senders to
compute increasingly complex source routes, the new Mail eXchanger
resource record contained the recipient's decision. Any host in the
DNS table could specify an alternate machine responsible for all its
incoming mail. Conversely, a single relay could aggregate mail for
several networks. New kinds of relays emerged, too: mailing list
servers that accepted a message and burst it out to a long list,
providing their own load-balancing, routing, and queue management.

The new world of mail began to look a lot like the very old: the
notion of poste restante, delivered to a regional depot (such as the
downtown post office or American Express branch) for a traveler to
rendezvous with. While SMTP connections came in from other Mail
Transfer Agents (MTAs), nomadic Mail User Agents (MUAs) used protocols
like PCMAIL or Post Office Protocol (POP) and now Interactive Message
Access Protocol (IMAP) to download and manage their mailboxes.
Two-phase delivery interrupts servers instantly with inbound mail, but
waits for users to poll for updates.

Mail Packets

IP exchanges packets between network interfaces; FTP exchanges files
between hosts; and SMTP exchanges messages between mailboxes. The
critical difference is that while we can quibble over the differences
between communicating with a host or one of its interfaces on the
connected Internet, mailboxes come from an entirely different, logical
set of endpoints. John Quarterman dubbed the wider world of e-mail
exchanging computers 'The Matrix,' in the spirit of William Gibsons's
original cyberpunk coinage. E-mail transfers reach out to systems well
beyond the reach of IP, and do so at the sender's bidding.

Its strategies for addressing (users and groups), distribution
(hierarchical aggregation), and content (MIME) give SMTP wide reach
and applicability. It may once have been built atop FTP, but now we
can use mail to access FTP archives, read news groups, browse web
sites, play chess, and more.

Upon reflection, mail messages are just the same as IP packets. Seven
layers up the stack, we recursively discover the same challenges as we
began with. Disparate notions of data transfer bridged by judicious
enveloping; gateways which can fragment and reassemble messages, and
improbable flexibility from text messages to bulk data transfer to
real-time multimedia and more. The same problems (and solutions)
arise, too: routing loops (and Time-To-Live bounds), asymmetric routes
(and source-routed mailboxes), transit size limits (and
message/partial fragmentation), rate limiting (and SMTP
implementations' queue throttling), end-to-end vs. hop-by-hop trust
(and key exchange between users and servers, respectively), and
resource rationing (and cost-based pricing).

For one, a lot of the claims made for Active Networking -- with its
programmable packets ("capsules") executing within routers start
making a lot more sense as programmable messages evaluated at


Next issue: NNTP and IRC.



Title and Comments


20 Jul 1971

Mail Box Protocol
Defined a remote "printer"; cosmetic user address on burst pages


14 Sep 1971

Comments on Mailbox Protocol
Terminal IMP users need two-phase delivery from central mailboxes


17 Nov 1971

Revision of the Mail Box Protocol
Mailbox files using FTP append-with-create and print formatting


5 Sep 1973

Standardizing Network Mail Headers
Introduced From:, Subject:, and Date: (with two-digit years!)


22 Jul 1974

On The Problem Of Signature Authentication For Network Mail
Reserved fixed port numbers for "authentic" mail service


8 Nov 1975

On the Junk Mail Problem
Postel proposed IMPs should track offending hosts -- appeared 20 years
later as the MAPS Realtime Black Hole List (


5 Aug 1976

Address Specification Syntax for Network Mail
ARPANET outgrew "real" names; added group aliases and sub-boxes


Sept 1980
May 1981

Mail Transfer Protocol (MTP)
New mail relay system based on FTP MAIL; part of NCP->TCP transition

STD 10

Aug 1982

Simple Mail Transfer Protocol (SMTP)
MAIL FROM, RCPT TO, and DATA; as well as interactive SEND

STD 11

Aug 1982

Standard for the Format of ARPA Internet Text Messages
Grammar for headings and field-value types (revised as ABNF, 2234)

STD 14

Jan 1986

Mail Routing and the Domain System
Defines the Mail eXchanger resource so mail relays serve many hosts


May 1986

PCMAIL: A Distributed Mail System for Personal Computers
Clients manage mail at a server; prototyped w/Unified Stream Protocol


Aug 1989
Feb 1993

Privacy-Enhanced Mail
New headers for public-key certificates; encryption req'd signature


Sep 1993
Nov 1996

Multipurpose Internet Mail Extensions
Not just multimedia & charsets! Revised into five Parts: body formats,
media types, internationalized headers, registration, and testing


Oct 1995

Security Multiparts & MIME Object Security Services
Defined Signed and Encrypted parts; uses any key pair or secret

STD 10

6 Nov 1995

SMTP Service Extensions (ESMTP)
Defined the EHLO+keyword+parameters negotiation framework


Jan 1996

Delivery Status Notifications, Multipart/Report, Enhanced Status Codes
Suite for automated verification and debugging undeliverable mail


May 1996
Oct 1984

Post Office Protocol -- Version 3
Clients pull mail; limited ability to preview headers and flush store


Dec 1996
Dec 1994

Interactive Message Access Protocol -- Version 4rev1
Clients manipulate mail folders at the server; shared folders, too


Mar 1997

MIME E-mail Encapsulation of Aggregate Documents, such as HTML
Related parts can be bound together, preserving internal URI rules


May 1997
May 1980

Mailbox Names for Common Roles, Services, and Functions
Common business, operations, services, mailing lists, and domain boxes


Mar 1998

An Extensible Message Format for Message Disposition Notifications
Indicates that mail has been read/processed, beyond merely delivered


July 1998

The mailto URL scheme
Encodes recipient as well as optional headers or body


July 1998

URLs as Meta-Syntax for Core Mail List Commands ...
List-Help, -(Un)Subscribe, -Post, and -Archive headers with mailto:

Table 1: Milestones in the fossil record of e-mail: protocols, message
formats, security, and operations






Creation time. Originally used 2-digit year; many forms in use


Originally Title; replies use Latin res, "in the matter of"
The other two fell into disuse in Mail; popular for News



Originally Author. Putative creator of the message


Actual sender, from the MAIL command. Used to delegate.


Followup address. But is it the sender alone, a group, a list?


To, Cc

Original and "carbon copy" recipients; at least one req'd


Blind CC; post separate copies to hide such recipients



Redistribution envelope when prefixed to above headings



Each mail relay logs when received, from whom, and protocol


Accumulated a reverse delivery pathway; deprecated.



Uniquely identifies the entire text+headers (except trace)


Can specify addresses and message-IDs this refers to; used to track
topics and threads of conversation.



Internet Media Type (with parameters) of the part's body


Uniquely identifies each body part; -MD5 uses hash function


Protection against 7-bit, linewidth-limited mail infrastructure.
Quoted-printable for text, Base64 for arbitrary 8-bit streams.
Actual character sets/languages are indicated elsewhere.



The URL of the resource that generated the entity represented in a
body part.


Relative URLs within a part are evaluated against this path



Sender's Message Integrity Code (e.g. digital signature)


Each recipient's Data Encryption Key to unlock the body

Table 2: A selection of standardized e-mail Message Headings.









Required greeting exchanges domain name and software version



Extended response enumerates site's supported Service Extensions



Negotiates whether to list (R)ecipients or (T)ext first; from FTP mail





FROM: <>; MTP can add TO: <> and go straight to DATA mode



TO: <> for each recipient; appears either before or after MAIL




TO: <> for each recipient; must appear before DATA command




Transmit message in NVT (Telnet) format until <CRLF>.<CRLF>



Deliver instantly to logged-in user, and/or mail (SAML, SOML)




Clear address and message buffers (implicit in HELO and ELHO)




<user> exists locally. Now required, though raises privacy risk




<alias> lists members. Now recommended, given privacy risk



Swap roles and delivery any queued mail for "client"; spoofing risk



Asks server to initiate reverse connection to process queued mail

Table 3: Required (+) and optional (-) commands in MTP, SMTP, and ESMTP.