Electronic Mail Security: SMTP & Sendmail

1
Electronic Mail SecuritySMTP Sendmail

• Cmpe 526 Operating System and Network Security
  Presentation
• Serdar Sali

2
Overview

• Introduction
• SMTP
• SMTP Security Issues
• Solutions to SMTP Security Issues
• Sendmail
• Sendmail security mechanisms

3
Introduction

• E-mail a leading communication medium
• As usage spreads, security issues arise
• Privacy, integrity, authentication
• Spamming
• Unsolited commercial - bulk e-mail

4
How e-mail works
5
SMTP

• Simple Mail Transfer Protocol
• Objective
• Transfer mail reliably and efficiently
• Independent of a particular transmission system
• Only a reliable ordered data channel required

6
SMTP

• Can relay mail across transport service
  environments
• SMTP transports a mail object
• Envelope and content
• A text based protocol

7
How SMTP works

• User wishes to send mail
• Client SMTP establishes two way transmission
  channel to Server SMTP
• Receiver may be ultimate or intermediate
• Client SMTP generates and sends SMTP messages
• Replies are sent from Server SMTP

8
How SMTP works
User
Client SMTP
Server SMTP
SMTP Commands/Replies
File System
File System
And mail
9
The SMTP Model

• A typical communication
• User establishes a connection
• Identifies using HELO or EHLO
• Sends mail using MAIL from ltaddressgt
• Specifies recipients using RCPT to ltaddressgt
• Specify mail content using DATA
• Close connection using QUIT or send another mail

10
The SMTP Model

• S MAIL FROM ltSmith_at_Alpha.ARPAgt
• R 250 OK
• S RCPT TO ltJones_at_Beta.ARPAgt
• R 250 OK
• S RCPT TO ltGreen_at_Beta.ARPAgt
• R 550 No such user here
• S RCPT TO ltBrown_at_Beta.ARPAgt
• R 250 OK
• S DATA
• R 354 Start mail input end with ltCRLFgt.ltCRLFgt
• S Blah blah blah...
• S ...etc. etc. etc.
• S ltCRLFgt.ltCRLFgt
• R 250 OK

11
The SMTP Model

• SMTP can be used for
• Mailing sending message to mailbox
• Sending sending message to users terminal if
  the user is online
• Usually, SMTP is used for sending, POP or IMAP is
  used for retrieval

12
SMTP Mail Relay

• The destination of the SMTP server may be final
  or intermediate
• The client resolves the server address to
• an intermediate Mail eXchanger host or
• a final target host.
• A server may be
• Ultimate destination
• Intermediate destination
• A gateway

13
SMTP Mail Relay

• Mail from ltreverse-pathgt
• Rcpt to ltforward-pathgt
• Two ways to relay messages
• Explicit source routing
• DNS Mail eXchanger (MX) records

14
SMTP Mail Relay

• Explicit Routing
• Forward path
• lt_at_a.com,_at_b.com,receiver_at_c.comgt
• Reverse path
• ltsender_at_d.comgt
• SMTP servers connected in order
• Each server removes its address and adds it to
  reverse path
• Error or notification messages
• Designed when internet was a small community

15
SMTP Mail Relay

• DNS MX records
• For a domain, search for a record in the DNS
• Forward the mail request to that host
• Currently used method for mail relay
• Explicit source routing still supported for
  backward compatibility
• This causes SPAM

domain
Preference value
host
16
SMTP Security Issues

• No authentication
• Spamming
• Unauthorized use of relaying, DoS
• All communication done in plaintext
• Eavesdropping
• Man in the middle attacks
• VRFY, EXPN commands

17
SMTP Security Issues

• SMTP-AUTH
• An extension that adds access control to SMTP
• A client may
• indicate an authentication mechanism to the
  server
• perform an authentication protocol exchange
• optionally negotiate a security layer for
  subsequent protocol interactions

18
SMTP-AUTH

• SMTP-AUTH
• Only legitimate users can relay mail
• Does not guarantee authenticity of envelope
  header or message header
• Spoofing is still possible
• The receiver can not tell if the sender was
  authenticated

19
SMTP-AUTH

• Based on Simple Authentication and Security Layer
  (SASL-RFC-2222)
• SASL uses plugins to define authentication
  mechanisms
• Plaintext password PLAIN
• Shared secretCRAM-MD5, DIGEST-MD5
• Kerberos KERBEROS_V4, GSSAPI

20
SMTP-AUTH

• Adds AUTH verb to SMTP
• Can take parameters to save round-trip
• Any knowledge prior to authentication must be
  discarded

21
SMTP-AUTH

• 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 PENCeUxFREJoU0NnbmhNWitOMjNGNndAZWx3b29kLml
  ubm9zb2Z0LmNvbT4
• C ZnJlZCA5ZTk1YWVlMDljNDBhZjJiODRhMGMyYjNiYmFlNzg
  2ZQ
• S 235 Authentication successful.

22
SMTP-AUTH

• AUTH verb can also be applied to mail from verb
• Allows trusted entities to communicate
  authentication of individual messages
• AUTHltgt not authenticated
• C MAIL FROMltemc2_at_example.comgt
  AUTHe3Dmc2_at_example.com
• S 250 OK

23
SMTP-AUTH

• Spoofing is still a problem
• Subject to man-in-the-middle attack
• Does not provide user authentication, only
  delivery authentication
• Subject to brute force attacks when username
  password schemes are used

24
Secure SMTP over TLS

• Private, authenticated communication between
  client and server
• Defines a new verb, STARTTLS
• Takes no parameters
• Used to tell client that the server is TLS
  capable
• Used to start a TLS handshake by client

25
Secure SMTP over TLS

• Sample communication
• S ltwaits for connection on TCP port 25gt
• C ltopens connectiongt
• S 220 mail.imc.org SMTP service ready
• C EHLO mail.ietf.org
• S 250-mail.imc.org offers a warm hug of welcome
• S 250 STARTTLS
• C STARTTLS
• S 220 Go ahead
• C ltstarts TLS negotiationgt
• C S ltnegotiate a TLS sessiongt
• C S ltcheck result of negotiationgt
• C ltcontinues by sending an SMTP commandgt . . .

26
Secure SMTP over TLS

• A publicly referenced SMTP server must not
  require TLS
• May effect relaying capabilities
• After the TLS handshake, client and server should
  give the decision
• Is the achieved authentication and privacy enough?

27
Secure SMTP over TLS

• If not
• Client should quit immediately,
• Server should respond each request with an error
  message
• Server may place info from certificate in
  Received header of the message body

28
Secure SMTP over TLS

• If security level is enough
• All info before handshake is discarded
• Client should send a EHLO again
• The server may report different services
• Security considerations
• Not end-to-end
• SMTP is not end-to-end
• The entire chain has to be made secure
• Does not indicate authentication for the
  receiving client

29
Secure SMTP over TLS

• Decision on adequateness of security
• Must be made locally
• Implementation dependent
• Susceptible to man-in-the-middle attack
• The STARTTLS response from server may be deleted
  by an eavesdropper
• Client never knows that server is TSL capable

30
Secure SMTP over TLS

• Solution to man-in-the-middle attack
• Client records if a server offers TLS
• Generates a warning if it is not offered in later
  sessions
• Can not be used to authenticate author
• Every chain needs to be authenticated
• Other mechanisms are used for this purpose
• PGP, MIME, etc.

31
POP-before-SMTP

• POP requires authentication
• A user uses POP to read mail
• IP address of that user is recorded
• User is granted access to SMTP server for a
  certain time period
• Dependent on user reading mail
• Not everyone uses POP
• May introduce risks with
• dynamic IPs
• NAT schemes

32
Sender Policy Framework

• An extension to SMTP
• Also called SMTP SPF
• Quick and easy to implement
• Designed to prevent forged e-mail
• Checks if the sender is authorized to send mail
  from the domain they claim to be from
• Two sides
• Checking incoming mail
• Other people checking mail you send

33
Sender Policy Framework

• To check incoming mail
• Use an SPF enabled message transfer agent
• To allow others check the mail you send
• Publish SPF records in DNS
• This domain sends mail only through these
  servers

34
Sender Policy Framework

• Types of DNS records used in SPF
• A maps name to IP address
• mail.example.com. IN A 192.0.2.3
• MX indicates servers responsible for handling
  mail in the domain
• example.com. IN MX 10 mail.example.com.
  example.com. IN MX 100 mailhandler.com
• PTR maps IP to name
• 6.1.36.36.in-addr.arpa. IN PTR example.com
• TXT arbitrary text strings up to 255 characters
  long

35
Sender Policy Framework

• Domains
• Identify which machines are allowed to send
  e-mail from that domain
• Add this info as a TXT record to their DNS info
• Receivers
• Must request and use SPF records

36
Sender Policy Framework

• An example SPF record
• vspf1 a mx a127.0.0.1
• amy.resolved.ip.com ptr all
• General format
• vspf1 pre type ... mod
• Pre specifies the result from a particular test
• Pass (Default)
• - Fail
• Softfail
• ? Neutral

37
Sender Policy Framework

• Type
• includedomain
• replace sender domain with given domain
• Use SPF record for that domain
• all
• Represents all other conditions
• a, adomain, adomain/cidr, a/cidr
• Requires an A record in DNS for sender domain
• mx, mxdomain,mxdomain/cidr, mx/cidr
• Requires an MX record in DNS for sender domain

38
Sender Policy Framework

• Type
• ptr, ptrdomain
• Requires a PTR record in DNS for sender IP
• ip4ipv4, ip4ipv4/cidr
• Used for defining valid IPv4s or IPv4 ranges
• ip6ipv6, ip6ipv6/cidr
• Used for defining valid IPv4s or IPv4 ranges
• existsdomain
• Requires existence of the domain

39
Sender Policy Framework

• Mod
• redirectdomain
• Redirects to SPF of indicated domain
• Functionally equivalent to include
• Can also be used after all to use redirect if all
  tests fail
• expTXT-RR
• Should come last in an SPF record
• Defines a DNS name whose TXT records may be
  returned as error messages

40
Sender Policy Framework

• Examples
• Only allow mail.example.com to send for
  example.com
• A receving MTA may also make an IP comparison

example.com. IN MX 10 mail.example.com. mail.examp
le.com. IN A 192.168.0.4 example.com. IN TXT
"vspf1 mx all" mail.example.com. IN TXT "vspf1
a -all"
41
Sender Policy Framework

• Examples
• Uses virtual domain
• Defines a valid IP range
• 192.168.0.0 192.168.0.31

vhost1.com. IN MX 10 mail.example.com vhost1.com.
IN TXT "vspf1 includeexample.com -all"
example.com. IN MX 10 mail.example.com. example.co
m. IN TXT "vspf1
ip4192.168.0.3/27 -all" mail.example.com. IN TXT
"vspf1 ip4192.168.0.3/27
-all"
42
Internal SMTP Issues

• Vrfy name
• Used to verify if a mailbox with the given name
  exists in an SMTP server
• Expn maillist-name
• Used to expand the members of the given maillist
  name
• Both sources of e-mail address for spammers
• Must be disabled

43
Sendmail

• An open source mail transfer agent
• Original version written by Eric Allman in 1980s
  at UC Berkeley
• Descendant of ARPANET delivermail
• Very flexible
• Supports different transfer and delivery
  protocols
• Very complicated
• Difficult to manage
• Configured using sendmail.cf, sendmail.mc
• Unfortunately, known for its bugs

44
Sendmail

• Security measures
• Sendmail restricted shell smrsh
• Standard security checks
• SMTP AUTH
• SMTP STARTTLS
• Rejecting SPAM
• Access database
• Anti-spamming relay features
• Validating senders

45
Sendmail

• Configuring sendmail
• /etc/mail/sendmail.cf
• Actual configuration file
• /etc/mail/sendmail.mc
• More user friendly configuration file
• Make sendmail.cf from sendmail.mc
• m4 /usr/local/share/sendmail/cf/m4/cf.m4
• /etc/mail/sendmail.mc gt /etc/mail/sendmail.cf

46
Sendmail

• Turning off exploitable features
• Find the line in sendmail.cf that contains
• O PrivacyOptions
• Add noexpn and novrfy
• O PrivacyOptionsnoexpn novrfy
• Most strict goaway
• Or set the confPRIVACY_FLAGS in sendmail.mc
• define(confPRIVACY_FLAGS, goaway, noexpn,
  novrfy, nobodyreturn)

47
Sendmail

• SMTP server banner
• May give away system info
• 220 192.168.1.1 ESMTP Sendmail 8.10.2Sun/8.10.2
  Tue,14 Jan 2003 09 2802-0500 (EST)
• Change SmtpGreetingMessage field in sendmail.cf

48
Sendmail

• Precautions against DoS attacks, in sendmail.mc
• Set confMAX_MESSAGE_SIZE to limit message size
• Set confMAX_DAEMON_CHILDREN to limit number of
  processes
• Does not prevent DoS attacks

49
Sendmail

• Controlled SMTP relaying in sendmail
  FEATURE(access_db)
• List the domains you are willing to relay from in
  /etc/mail/relay-domains
• FEATURE(relay_hosts_only)
• Hosts must also be listed
• FEATURE(relay_entire_domain)
• Relay all computers in domain
• FEATURE(access_db)
• Enables or disables access database
• FEATURE(blacklist_recipients)
• Also look up recipients in access database

50
Sendmail

• Controlled SMTP relaying in sendmail
• List the domains you are willing to relay from in
  /etc/mail/relay-domains
• FEATURE(dnsbl)
• Use realtime black hole list at mail-abuse.org
• 1.5.5.192.blackholes.mail-abuse.org 
• IN A 127.0.0.2
• FEATURE(accept_unqualified_senders)
• Allow users without domains
• FEATURE(accept_unresolvable_domains)
• Allow users with unresolvable domains
• FEATURE(relay_based_on_MX)
• Permit any relay directed to your host

51
Sendmail

• Following features make vulnerable to abuse
• FEATURE(relay_local_from).
• Allows relaying if the message claims to
  originate at your domain.
• FEATURE(loose_relay_check).
• turns off checking for explicit routing
• FEATURE(promiscuous_relay).
• turn off all checking for relaying.

52
Sendmail

• Access database
• In /etc/mail/access
• Allow access by individual domains
• Two-tuples key action
• Key
• Fully or partly qualified host name
• Network or subnetwork address
• Specific e-mail addresses
• Can also include FROM, TO, etc.

53
Sendmail

• Actions
• REJECT
• refuse connections from host
• DISCARD
• accept the message but silently discard it,
  sender will think message is accepted
• OK
• Allow access, overrides other checks
• RELAY
• Allow access including relaying
• ERROR arbitrary message
• Reject mail with customized message

54
Sendmail

• Example
• cyberpromo.com REJECT
• sendmail.org RELAY
• spam_at_buyme.com ERROR550 Spammers do not live
  here anymore
• Froma_at_b.com REJECT
• Toc_at_d.com REJECT
• 193.140 RELAY
• Generate database from map
• makemap hash
• /etc/mail/access lt /etc/mail/access

55
Sendmail

• smrsh (Sendmail restricted shell)
• aliases database
• alias mailing list
• forwarding mail
• .forward file in home directory
• In addition to mail addresses, commands may also
  be used
• A malicious user can execute commands using the
  sent mail

56
Sendmail

• smsrh
• Form an explicit list of executables that
  sendmail is allowed to execute
• sendmail.mc FEATURE(smsrh)
• Directory for allowed executables
• /usr/libexec/sm.bin
• Any reference to executables appended with this
  directory
• Should be carefully populated
• Advised to be used in all sendmail versions

57
Sendmail

• Enhanced File Security
• Tight rules for opening files
• In general, all read directories should be owned
  by root
• No .forward in unsafe (group or world writable)
  directories

58
Sendmail

• Enhanced File Security
• If too restrictive, set the DontBlameSendmail
  option in sendmail.mc
• define
• (confDONT_BLAME_SENDMAIL,...)
• ForwardFileInUnsafeDirPath
• Allow .forward files in unsafe directories.
• ForwardFileInUnsafeDirPathSafe
• Allow a .forward file that is in an unsafe
  directory to include references to program and
  files.

59
Sendmail

• SMTP-Auth in sendmail
• Install an SASL library
• i.e. Cyrus SASL
• Compile sendmail with right options
• APPENDDEF(confENVDEF', -DSASL')
  APPENDDEF(conf_sendmail_LIBS', -lsasl')
• for Cyrus SASLv1
• APPENDDEF(confENVDEF', -DSASL2')
  APPENDDEF(conf_sendmail_LIBS', -lsasl2')
• for Cyrus SASLv2
• to site.config.m4

60
Sendmail

• Set options in sendmail.mc
• TRUST_AUTH_MECH(GSSAPI DIGEST-MD5')dnl
• define(confAUTH_MECHANISMS', GSSAPI
  DIGEST-MD5')dnl
• define(confDEF_AUTH_INFO', /etc/mail/auth/auth-i
  nfo')dnl
• DAEMON_OPTIONS(a')dnl
• Requiring SMTP AUTH
• Delete all other means of relaying

61
Sendmail

• To use as client,generate an info file
• client-info AuthInfoyour.isp.net "Uroot"
  "Ppassword
• Generate authentication database
• makemap hash client-info lt client-info
• Edit configuration file
• define(SMART_HOST',your.isp.net')
• define(confAUTH_MECHANISMS', DIGEST-MD5
  CRAM-MD5 LOGIN PLAIN')
• FEATURE(authinfo',hash /etc/mail/auth/client-inf
  o')

62
Sendmail

• SMTP STARTTLS in sendmail
• Allow relaying based on certificates
• Restrict incoming or outgoing connections
• Define following variables
• define(confCACERT_PATH', /etc/mail/certs/')
• define(confCACERT', /etc/mail/certs/CA.cert.pem'
  )
• define(confSERVER_CERT', /etc/mail/certs/my.cert
  .pem')
• define(confSERVER_KEY', /etc/mail/certs/my.key.p
  em')

63
Sendmail

• verify macro that keeps result of
  verification
• OK verification succeeded.
• NO no cert presented.
• NOT no cert requested.
• FAIL cert presented but could not be verified,
  e.g., the cert of the signing CA is
  missing.
• NONE STARTTLS has not been performed.
• TEMP temporary error occurred.
• PROTOCOL protocol error occurred (SMTP level).
• SOFTWARE STARTTLS handshake failed.

64
Sendmail

• Relaying based on certificates
• If sender not verified, usual relaying
• If verified, look up the domain of certificate
  issuer, and check access database for that domain
• If result is RELAY, relay
• If result is SUBJECT, look up the subject

65
Sendmail

• Example
• To allow relaying only for a subset of machines
  that have a cert signed by
• /CUS/STCalifornia/Oendmail.org/OUprivate/CN
  Darth20Mail2028Cert29/Emaildarth2Bcert_at_endma
  il.org
• use
• CertIssuer/CUS/STCalifornia/Oendmail.org/OUpr
  ivate/CNDarth20Mail2028Cert29/Emaildarth2Bc
  ert_at_endmail.org
  SUBJECT
• CertSubject/CUS/STCalifornia/Oendmail.org/OUp
  rivate/CN DeathStar/Emaildeathstar_at_endmail.org
  RELAY
• Received header
• (versiontls_version ciphercipher
  bitscipher_bits verifyverify)

66
Sendmail

• Deciding to continue communication
• Two-tuples in access map
• Key clients or servers
• Values
• VERIFY successful verification required
• VERIFYbits successful verification required
  cipher bits gt bits
• ENCRbits cipher bits gt bits
• TLS_Srv, TLS_Clt keywords

67
Sendmail

• Example
• TLS_Srvsecure.example.com ENCR112
• TLS_Cltlaptop.example.com VERIFY112
• E-mail sent to secure.example.com should be
  encrypted
• E-mail sent from laptop.example.com should be
  authenticated

68
Sendmail

• Known application bugs and exploits
• CERT advisories, www.cert.org
• Do not run sendmail as root
• Current versions do not
• Sendmail X new generation of sendmail
• Similar to Postfix architecture

69
Conclusion

• Spamming is a serious issue
• Open mail relays
• Open proxies
• Worms that make servers vulnerable
• Methods presented here do not provide end-to-end
  security
• PGP, S/MIME must be used

70
Questions?
71
Questions?

• Thank you!