1. Electronic mail – protocol evolution

2. E-mail standards

3. Electronic Mail Three major components: user agents mail servers simple mail transfer protocol: SMTP, TCP port 25 User Agent a.k.a. “mail reader” composing, editing, reading mail messages e.g., Eudora, Outlook, elm, Netscape Messenger outgoing, incoming messages stored on server user mailbox outgoing message queue mail server user agent user agent user agent mail server user agent user agent mail server user agent SMTP

4. Email terminology

5. SMTP (RFC 821)

6. Sample SMTP interaction: TCP port 25 S: 220 hamburger.edu C: HELO crepes.fr S: 250 Hello crepes.fr, pleased to meet you C: MAIL FROM: S: 250 alice@crepes.fr... Sender ok C: RCPT TO: S: 250 bob@hamburger.edu... Recipient ok C: DATA S: 354 Enter mail, end with "." on a line by itself C: Do you like ketchup? C: How about pickles? C:. S: 250 Message accepted for delivery C: QUIT S: 221 hamburger.edu closing connection

7. Mail Standard RFC822 Published in 1982 Lines no longer than 1000 char Message body - plain US-ASCII text Message header lines - plain US-ASCII text Limit on message length

8. RFC 822 format

9. RFC 822 restrictions no multiple objects in a single message no multi-part message bodies no non-textual bodies no X.400 messages can be gatewayed no multifont messages

10. ASCII times are over! Now we want: National language support Possibility to send –pictures –audiofiles –other applications –video files –multimedia applications

11. MIME - Multipurpose Internet Mail Extension RFC 2045-2048 obsolete RFC 1521, 1522,1590 RFC 2045 Format of Internet Message Bodies RFC 2046 Media Types RFC 2047 Message Header Extension for Non-ASCII Text RFC 2048 Registration Procedures To solve RFC822 restrictions without serious incompatibilities with it

12. MIME

13. MIME types and sub-types

14. base64 encoding

15. Mail message format SMTP: protocol for exchanging email msgs RFC 822: standard for text message format: header lines, e.g., –To: –From: –Subject: different from SMTP commands! body –the “message”, 7-bit ASCII characters only header body blank line

16. Message format: multimedia extensions MIME: multimedia mail extension, RFC 2045, 2056 additional lines in msg header declare MIME content type From: alice@crepes.fr To: bob@hamburger.edu Subject: Picture of yummy crepe. MIME-Version: 1.0 Content-Transfer-Encoding: base64 Content-Type: image/jpeg base64 encoded data....................................base64 encoded data multimedia data type, subtype, parameter declaration method used to encode data MIME version encoded data

17. Multipart Type From: alice@crepes.fr To: bob@hamburger.edu Subject: Picture of yummy crepe. MIME-Version: 1.0 Content-Type: multipart/mixed; boundary=98766789 --98766789 Content-Transfer-Encoding: quoted-printable Content-Type: text/plain Dear Bob, Please find a picture of a crepe. --98766789 Content-Transfer-Encoding: base64 Content-Type: image/jpeg base64 encoded data....................................base64 encoded data --98766789--

18. Multipart Type From: alice@crepes.fr To: bob@hamburger.edu Subject: Picture of yummy crepe. MIME-Version: 1.0 Content-Type: multipart/mixed; boundary=StartOfNextPart --StartOfNextPart Dear Bob, Please find a picture of a crepe. --StartOfNextPart Content-Transfer-Encoding: base64 Content-Type: image/jpeg base64 encoded data....................................base64 encoded data --StartOfNextPart Do you want the reciple?

19. Mail access protocols SMTP: delivery/storage to receiver’s server Mail access protocol: retrieval from server –POP: Post Office Protocol [RFC 1939] authorization (agent server) and download –IMAP: Internet Mail Access Protocol [RFC 1730] more features (more complex) manipulation of stored msgs on server –HTTP: Hotmail, Yahoo! Mail, etc. user agent sender’s mail server user agent SMTP access protocol receiver’s mail server

20. Try SMTP interaction for yourself: telnet servername 25 see 220 reply from server enter HELO, MAIL FROM, RCPT TO, DATA, QUIT commands above lets you send email without using email client (reader)

21. Post Office Protocol (POP3)

23. POP3 protocol authorization phase client commands: –user: declare username –pass: password server responses –+OK –-ERR transaction phase, client: list: list message numbers retr: retrieve message by number dele: delete quit C: list S: 1 498 S: 2 912 S:. C: retr 1 S: S:. C: dele 1 C: retr 2 S: S:. C: dele 2 C: quit S: +OK POP3 server signing off S: +OK POP3 server ready C: user bob S: +OK C: pass hungry S: +OK user successfully logged on

24. IMAP

25. Web Mail http://www.squirrelmail.org

26. (Adjusted) Mail Architecture petrel alpha admsrvcs Anti-virus Director Content Filter Off-Campus E-mail Antispam

28. Outgoing mail authentication RDC 2554 S: 220 smtp.example.com ESMTP server ready C: EHLO jgm.example.com S: 250-smtp.example.com S: 250 AUTH CRAM-MD5 DIGEST-MD5 C: AUTH FOOBAR S: 504 Unrecognized authentication type. C: AUTH CRAM-MD5 S: 334 U0NnbmhNWitOMjNGNndAZWx3b29kLmlubm9zb2Z0LmNvbT4= C: ZnJlZCA5ZTk1YWVlMDljNDBhZjJiODRhMGMyYjNiYmFlNzg2ZQ== S: 235 Authentication successful. S: 220 smtp.example.com ESMTP server ready C: EHLO jgm.example.com S: 250-smtp.example.com S: 250 AUTH CRAM-MD5 DIGEST-MD5 C: AUTH FOOBAR S: 504 Unrecognized authentication type. C: AUTH CRAM-MD5 S: 334 U0NnbmhNWitOMjNGNndAZWx3b29kLmlubm9zb2Z0LmNvbT4= C: ZnJlZCA5ZTk1YWVlMDljNDBhZjJiODRhMGMyYjNiYmFlNzg2ZQ== S: 235 Authentication successful.

30. Spam mail Return-Path: Delivered-To: guntis@latnet.lv Received: from server.thirdstone.net (unknown [66.216.98.139]) by pumpis4.latnet.lv (Postfix) with ESMTP id C09DF4943B for ; Fri, 24 Mar 2006 15:34:29 +0200 (EET) Received: by server.thirdstone.net (Postfix, from userid 80) id 2628636A33E; Fri, 24 Mar 2006 05:40:35 -0800 (PST) To: guntis@latnet.lv Subject: Your online account has been limited From: Chase Card Services Online Services Team Content-Type: text/html Message-Id: Date: Fri, 24 Mar 2006 05:40:35 -0800 (PST) X-Virus-Scanned: amavisd-new 2.3.2 (20050629) at latnet.lv X-Spam-Status: No, hits=5.448 tagged_above=0 required=7 tests=[BAYES_40=-0.002, HTML_40_50=0.496, HTML_IMAGE_ONLY_32=1.052, HTML_MESSAGE=0.001, HTML_TAG2=0.1, MESSAGE_ID_EXIST1=-0.1, MESSAGE_ID_EXIST2=-0.1, MIME_HEADER_CTYPE_ONLY=0, MIME_HTML_ONLY=0.001, NO_DNS_FOR_FROM=3.2, ONLINE_IN_BODY=0.1, SARE_RD_GOOGLE=0.8, URL_STARTS_WITH_WWW=-0.1] X-Spam-Level: ***** Return-Path: Delivered-To: guntis@latnet.lv Received: from server.thirdstone.net (unknown [66.216.98.139]) by pumpis4.latnet.lv (Postfix) with ESMTP id C09DF4943B for ; Fri, 24 Mar 2006 15:34:29 +0200 (EET) Received: by server.thirdstone.net (Postfix, from userid 80) id 2628636A33E; Fri, 24 Mar 2006 05:40:35 -0800 (PST) To: guntis@latnet.lv Subject: Your online account has been limited From: Chase Card Services Online Services Team Content-Type: text/html Message-Id: Date: Fri, 24 Mar 2006 05:40:35 -0800 (PST) X-Virus-Scanned: amavisd-new 2.3.2 (20050629) at latnet.lv X-Spam-Status: No, hits=5.448 tagged_above=0 required=7 tests=[BAYES_40=-0.002, HTML_40_50=0.496, HTML_IMAGE_ONLY_32=1.052, HTML_MESSAGE=0.001, HTML_TAG2=0.1, MESSAGE_ID_EXIST1=-0.1, MESSAGE_ID_EXIST2=-0.1, MIME_HEADER_CTYPE_ONLY=0, MIME_HTML_ONLY=0.001, NO_DNS_FOR_FROM=3.2, ONLINE_IN_BODY=0.1, SARE_RD_GOOGLE=0.8, URL_STARTS_WITH_WWW=-0.1] X-Spam-Level: ***** Return-Path: Received: from fifa.org (218-175-82-64.dynamic.hinet.net [218.175.82.64]) by alfred.taide.net (Postfix) with SMTP id 675FB3430E for ; Sun, 26 Mar 2006 11:12:52 +0200 (CEST) Message-ID: Reply-To: "Aegle Freudenburg" From: "Aegle Freudenburg" To: guntis.barzdins@taide.net Subject: Re: new Date: Sun, 26 Mar 2006 04:12:15 -0500 X-Virus-Scanned: by amavisd-new at taide.net X-Spam-Status: GOOD 0.0000000 4d8e508788a7565e07ee1405c73c45f1 Return-Path: Received: from fifa.org (218-175-82-64.dynamic.hinet.net [218.175.82.64]) by alfred.taide.net (Postfix) with SMTP id 675FB3430E for ; Sun, 26 Mar 2006 11:12:52 +0200 (CEST) Message-ID: Reply-To: "Aegle Freudenburg" From: "Aegle Freudenburg" To: guntis.barzdins@taide.net Subject: Re: new Date: Sun, 26 Mar 2006 04:12:15 -0500 X-Virus-Scanned: by amavisd-new at taide.net X-Spam-Status: GOOD 0.0000000 4d8e508788a7565e07ee1405c73c45f1 SMTP: MAIL FROM: SMTP: HELO server.thirdstone.net Reverse DNS lookup

31. Mail from El Presidente Return-Path: Delivered-To: steve@blighty.com Received: from fake-name.example.com (unknown [64.71.176.18]) by gp.word-to-the-wise.com (Postfix) with SMTP id 3DD7790000D for ; Tue, 2 Dec 2003 12:55:36 -0800 (PST) From: El Presidente To: Steve Atkins Subject: Fake Mail Message-Id: Date: Tue, 2 Dec 2003 12:55:36 -0800 (PST) Status: RO Content-Length: 15 Lines: 1 Some body text

32. Sending spam (relay hijacking) SMTP POP3 SMTP Third-party mailserver (10.11.12.13) Recipients MX Spammer (64.71.176.18)

33. Sending spam (relay hijacking) Received: from openrelay.com (mail.openrelay.com [10.11.12.13]) by gp.word-to-the-wise.com (Postfix) with SMTP id 3DD7790000D for ; Tue, 2 Dec 2003 12:55:36 -0800 (PST) Received: from fake-spammer-helo (spammer.net [64.71.176.18]) by openrelay.com (Postfix) with SMTP id 3DD7790000D for ; Tue, 2 Dec 2003 12:55:36 -0800 (PST) You can see the relay, and the original spammer

34. Sending spam (direct to MX) SMTPPOP3 Recipients MX Spammer (64.71.176.18)

35. Sending spam (direct to MX) Received: from fake-spammer-helo (spammer.net [64.71.176.18]) by gp.word-to-the-wise.com (Postfix) with SMTP id 3DD7790000D for ; Tue, 2 Dec 2003 12:55:36 -0800 (PST) You can see the spammer

36. Sending spam (proxy hijacking) HTTP POP3 SMTP Open proxy (192.168.1.1) Recipients MX Spammer (64.71.176.18)

37. Sending spam (proxy hijacking) Received: from fake-spammer-helo (open-proxy.net [192.168.1.1]) by gp.word-to-the-wise.com (Postfix) with SMTP id 3DD7790000D for ; Tue, 2 Dec 2003 12:55:36 -0800 (PST) You can see the open proxy

38. Mapping email to postal mail- the envelope Mail From / Envelope From / Return Path Recipient To ~ Sender ID’s authorization proof

39. Email Authentication Proposals (not directly related to spam!) Client SMTP Validation (CSV): –http://www.ietf.org/internet-drafts/draft-ietf-marid-csv-intro-01.txthttp://www.ietf.org/internet-drafts/draft-ietf-marid-csv-intro-01.txt Bounce Address Tag Validation (BATV): –http://www.ietf.org/internet-drafts/draft-levine-mass-batv-00.txthttp://www.ietf.org/internet-drafts/draft-levine-mass-batv-00.txt DomainKeys: –http://antispam.yahoo.com/domainkeyshttp://antispam.yahoo.com/domainkeys Identified Internet Mail (IIM): –http://www.ietf.org/internet-drafts/draft-fenton-identified-mail-01.txthttp://www.ietf.org/internet-drafts/draft-fenton-identified-mail-01.txt Sender ID (SPF + PRA): –http://www.ietf.org/internet-drafts/draft-ietf-marid-pra-00.txthttp://www.ietf.org/internet-drafts/draft-ietf-marid-pra-00.txt –http://www.ietf.org/internet-drafts/draft-ietf-marid-core-03.txthttp://www.ietf.org/internet-drafts/draft-ietf-marid-core-03.txt

40. SPF: Sender Policy Framework Domains use public records (DNS) to direct requests for different services (web, email, etc.) to the machines that perform those services. All domains already publish email (MX) records to tell the world what machines receive mail for the domain. SPF works by domains publishing "reverse MX" records to tell the world what machines send mail from the domain. When receiving a message from a domain, the recipient can check those records to make sure mail is coming from where it should be coming from. With SPF, those "reverse MX" records are easy to publish: one line in DNS is all it takes. Domains use public records (DNS) to direct requests for different services (web, email, etc.) to the machines that perform those services. All domains already publish email (MX) records to tell the world what machines receive mail for the domain. SPF works by domains publishing "reverse MX" records to tell the world what machines send mail from the domain. When receiving a message from a domain, the recipient can check those records to make sure mail is coming from where it should be coming from. With SPF, those "reverse MX" records are easy to publish: one line in DNS is all it takes.

41. DomainKeys Under DomainKeys, a domain owner generates one or more private/public key-pairs that will be used to sign messages originating from that domain. The domain owner places the public-key in his domain namespace (i.e., in a DNS record associated with that domain), and makes the private-key available to the outbound email system. When an email is submitted by an authorized user of that domain, the email system uses the private-key to digitally sign the email associated with the sending domain. The signature is added as a "DomainKey-Signature:" header to the email, and the message is transferred to its recipients in the usual way. When a message is received with a DomainKey signature header, the receiving system can verify the signature as follows: 1. Extract the signature and claimed sending domain from the email. 2. Fetch the public-key from the claimed sending domain namespace. 3. Use public-key to determine whether the signature of the email has been generated with the corresponding private-key, and thus whether the email was sent with the authority of the claimed sending domain. In the event that an email arrives without a signature or when the signature verification fails, the receiving system retrieves the policy of the claimed sending domain to ascertain the preferred disposition of such email. Under DomainKeys, a domain owner generates one or more private/public key-pairs that will be used to sign messages originating from that domain. The domain owner places the public-key in his domain namespace (i.e., in a DNS record associated with that domain), and makes the private-key available to the outbound email system. When an email is submitted by an authorized user of that domain, the email system uses the private-key to digitally sign the email associated with the sending domain. The signature is added as a "DomainKey-Signature:" header to the email, and the message is transferred to its recipients in the usual way. When a message is received with a DomainKey signature header, the receiving system can verify the signature as follows: 1. Extract the signature and claimed sending domain from the email. 2. Fetch the public-key from the claimed sending domain namespace. 3. Use public-key to determine whether the signature of the email has been generated with the corresponding private-key, and thus whether the email was sent with the authority of the claimed sending domain. In the event that an email arrives without a signature or when the signature verification fails, the receiving system retrieves the policy of the claimed sending domain to ascertain the preferred disposition of such email. $ openssl rsa -in rsa.private -out rsa.public -pubout -outform PEM -----BEGIN PUBLIC KEY----- MHwwDQYJKoZIhvcNAQEBBQADawAwaAJhAKJ2lzDLZ8XlVambQfMXn3LRGKOD5o6l MIgulclWjZwP56LRqdg5ZX15bhc/GsvW8xW/R5Sh1NnkJNyL/cqY1a+GzzL47t7E XzVc+nRLWT1kwTvFNGIoAUsFUq+J6+OprwIDAQAB -----END PUBLIC KEY----- This public-key data is placed in the DNS: _domainkey IN TXT "t=y; o=-; n=notes; r=emailAddress" $ openssl rsa -in rsa.private -out rsa.public -pubout -outform PEM -----BEGIN PUBLIC KEY----- MHwwDQYJKoZIhvcNAQEBBQADawAwaAJhAKJ2lzDLZ8XlVambQfMXn3LRGKOD5o6l MIgulclWjZwP56LRqdg5ZX15bhc/GsvW8xW/R5Sh1NnkJNyL/cqY1a+GzzL47t7E XzVc+nRLWT1kwTvFNGIoAUsFUq+J6+OprwIDAQAB -----END PUBLIC KEY----- This public-key data is placed in the DNS: _domainkey IN TXT "t=y; o=-; n=notes; r=emailAddress"

42. DomainKeys Example DomainKey-Status: good DomainKey-Signature: a=rsa-sha1; s=brisbane; d=football.example.com; c=simple; q=dns; b=dzdVyOfAKCdLXdJOc9G2q8LoXSlEniSbav+yuU4zGeeruD00lszZ VoG4ZHRNiYzR; Received: from dsl-10.2.3.4.football.example.com [10.2.3.4] by submitserver.football.example.com with SUBMISSION; Fri, 11 Jul 2003 21:01:54 -0700 (PDT) From: "Joe SixPack" To: "Suzie Q" Subject: Is dinner ready? Date: Fri, 11 Jul 2003 21:00:37 -0700 (PDT) Message-ID: Hi. We lost the game. Are you hungry yet? Joe. DomainKey-Status: good DomainKey-Signature: a=rsa-sha1; s=brisbane; d=football.example.com; c=simple; q=dns; b=dzdVyOfAKCdLXdJOc9G2q8LoXSlEniSbav+yuU4zGeeruD00lszZ VoG4ZHRNiYzR; Received: from dsl-10.2.3.4.football.example.com [10.2.3.4] by submitserver.football.example.com with SUBMISSION; Fri, 11 Jul 2003 21:01:54 -0700 (PDT) From: "Joe SixPack" To: "Suzie Q" Subject: Is dinner ready? Date: Fri, 11 Jul 2003 21:00:37 -0700 (PDT) Message-ID: Hi. We lost the game. Are you hungry yet? Joe. DNS TXT query for: brisbane._domainkey.football.example.com DNS TXT query for: brisbane._domainkey.football.example.com

43. DNS to distribute Domain-Level Keys [DomainKeys]

44. DomainKeys

45. intra-domain authentication? SK must be online mail-forwarding services?

46. Autentisks E-mails no ft.com guntis@gulbis:~$ nslookup > set type=any > uk.update.ft.com Server: 159.148.108.1 Address: 159.148.108.1#53 Non-authoritative answer: Name: uk.update.ft.com Address: 64.73.138.246 uk.update.ft.com mail exchanger = 10 uk.update.ft.com. uk.update.ft.com text = "v=spf1 ip4:64.73.138.0/24 -all“ > ftcom._domainkey.uk.update.ft.com Server: 159.148.108.1 Address: 159.148.108.1#53 Non-authoritative answer: ftcom._domainkey.uk.update.ft.com text = "k=rsa\; p=MIGfMA0GCSqGSIb3DQEBAQUAA4GNADCBiQKBgQCoNyixo7zQAb2mLAhB29hV6a7djDXrTZBo67Wa+j XykAt0O1vFhaLE1p5bFJnqhQzgmT91eVw58/Y2+MWqusiPrzycSQl7FNsmPW2iFqmO5wJbaytjkqvS5D wEiB4aHGQyCbi1Vobs7INFy1SAATdzqXFD8GNKNZRuf5fmqHvesQIDAQAB" > guntis@gulbis:~$ nslookup > set type=any > uk.update.ft.com Server: 159.148.108.1 Address: 159.148.108.1#53 Non-authoritative answer: Name: uk.update.ft.com Address: 64.73.138.246 uk.update.ft.com mail exchanger = 10 uk.update.ft.com. uk.update.ft.com text = "v=spf1 ip4:64.73.138.0/24 -all“ > ftcom._domainkey.uk.update.ft.com Server: 159.148.108.1 Address: 159.148.108.1#53 Non-authoritative answer: ftcom._domainkey.uk.update.ft.com text = "k=rsa\; p=MIGfMA0GCSqGSIb3DQEBAQUAA4GNADCBiQKBgQCoNyixo7zQAb2mLAhB29hV6a7djDXrTZBo67Wa+j XykAt0O1vFhaLE1p5bFJnqhQzgmT91eVw58/Y2+MWqusiPrzycSQl7FNsmPW2iFqmO5wJbaytjkqvS5D wEiB4aHGQyCbi1Vobs7INFy1SAATdzqXFD8GNKNZRuf5fmqHvesQIDAQAB" > Return-Path: Delivered-To: guntis@latnet.lv Received: from update.ft.com (transit246.email.mms.eloyalty.net [64.73.138.246]) by pumpis4.latnet.lv (Postfix) with ESMTP id 5B0115A5DB for ; Tue, 28 Mar 2006 15:10:43 +0300 (EEST) DomainKey-Signature: a=rsa-sha1; c=nofws; q=dns; s=ftcom; d=uk.update.ft.com; b=oILD038lHibyKsc7uPFA3Qx7n7CwegCQeNOAOIg+BZ3ZG+aIE68Mc5zB6FdHrJlWb+yxzkYOlqmf 8Qqzc2rmJXOtwtEFgO4BGUYpmGa6mYvXohBJC8Lf5CFbnyr0UjuGVzU46O249STEJ88e+A5eN3ep 9OvvBrSxGJ9HPnGHdsE=; Received: by update.ft.com (PowerMTA(TM) v3.0r11) id h54jse07d1s6 for ; Tue, 28 Mar 2006 06:10:39 -0600 (envelope-from ) From: "FT.com" To: Subject: The latest news and features on FT.com Date: Tue, 28 Mar 2006 06:10:42 -0600 Message-ID: Content-Return: allowed MIME-Version: 1.0 Content-Transfer-Encoding: quoted-printable Content-Type: text/html; charset="iso-8859-1" X-Virus-Scanned: amavisd-new 2.3.2 (20050629) at latnet.lv Return-Path: Delivered-To: guntis@latnet.lv Received: from update.ft.com (transit246.email.mms.eloyalty.net [64.73.138.246]) by pumpis4.latnet.lv (Postfix) with ESMTP id 5B0115A5DB for ; Tue, 28 Mar 2006 15:10:43 +0300 (EEST) DomainKey-Signature: a=rsa-sha1; c=nofws; q=dns; s=ftcom; d=uk.update.ft.com; b=oILD038lHibyKsc7uPFA3Qx7n7CwegCQeNOAOIg+BZ3ZG+aIE68Mc5zB6FdHrJlWb+yxzkYOlqmf 8Qqzc2rmJXOtwtEFgO4BGUYpmGa6mYvXohBJC8Lf5CFbnyr0UjuGVzU46O249STEJ88e+A5eN3ep 9OvvBrSxGJ9HPnGHdsE=; Received: by update.ft.com (PowerMTA(TM) v3.0r11) id h54jse07d1s6 for ; Tue, 28 Mar 2006 06:10:39 -0600 (envelope-from ) From: "FT.com" To: Subject: The latest news and features on FT.com Date: Tue, 28 Mar 2006 06:10:42 -0600 Message-ID: Content-Return: allowed MIME-Version: 1.0 Content-Transfer-Encoding: quoted-printable Content-Type: text/html; charset="iso-8859-1" X-Virus-Scanned: amavisd-new 2.3.2 (20050629) at latnet.lv