Computer Security:

Principles and Practice

Fourth Edition

By: William Stallings and Lawrie Brown

Chapter 22
Internet Security Protocols and
Standards
 MIME and S/MIME
MIME S/MIME
• Extension to the old RFC • Secure/Multipurpose
822 specification of an Internet Mail Extension
Internet mail format
• RFC 822 defines a simple
• Security enhancement to
heading with To, From, the MIME Internet
Subject e-mail format
• Assumes ASCII text format • Based on technology from
• Provides a number of RSA Data Security

new header fields that • Provides the ability to

define information about sign and/or encrypt
the body of the message e-mail messages
 Table 22.1
S/MIME Content Types
 S/MIME Functions
Signed and
Enveloped Signed Clear-
enveloped
data data signed data
data

Cleartext
Encrypte Nesting
Encoded message
d content of signed
message +
and and
+ signed encoded
associate encrypte
digest signed
d keys d entities
digest
Signed and Clear-Signed Data
• The preferred algorithms used for signing S/MIME
messages use either an RSA or a DSA signature of a SHA-
256 message hash
• The process works as follows:
• Take the message you want to send and map it into a fixed-length code of 256
bits using SHA-256
• The 256-bit message digest is unique for this message making it virtually
impossible for someone to alter this message or substitute another message
and still come up with the same digest
• S/MIME encrypts the digest using RSA and the sender’s private RSA key
• The result is the digital signature, which is attached to the message
• Now, anyone who gets the message can recompute the message digest then
decrypt the signature using RSA and the sender’s public RSA key
• Since this operation only involves encrypting and decrypting a 256-bit block,
it takes up little time
 Enveloped Data
• Default algorithms used for encrypting S/MIME
messages are AES and RSA
• S/MIME generates a pseudorandom secret key that is used to
encrypt the message using AES or some other conventional
encryption scheme
• A new pseudorandom key is generated for each new message
encryption
• This session key is bound to the message and transmitted with it
• The secret key is used as input to the public-key encryption
algorithm, RSA, which encrypts the key with the recipient’s public
RSA key
• On the receiving end, S/MIME uses the receiver's private RSA key
to recover the secret key, then uses the secret key and AES to
recover the plaintext message
• If encryption is used alone, radix-64 is used to convert the
ciphertext to ASCII format
 DomainKeys Identified
Mail (DKIM)
• Specification of cryptographically signing e-mail
messages permitting a signing domain to claim
responsibility for a message in the mail stream
• Proposed Internet Standard (RFC 4871:
DomainKeys Identified Mail (DKIM) Signatures)
• Has been widely adopted by a
range of e-mail providers
Secure Sockets Layer (SSL) and
Transport Layer Security (TLS)
• One of the most widely Two
used security services implementation
choices:
• General-purpose service
implemented as a set of
protocols that rely on Provided as part
TCP of the underlying
protocol suite

• Subsequently became
Internet standard
RFC4346: Transport Embedded in
Layer Security (TLS) specific packages
 TLS Concepts
TLS Session TLS Connection
• An association between a • A transport (in the OSI
client and a server layering model
• Created by the Handshake definition) that provides a
Protocol suitable type of service
• Define a set of • Peer-to-peer relationships
cryptographic security
parameters
• Transient

• Used to avoid the expensive

• Every connection is
negotiation of new security
associated with one
parameters for each session
connection
Change Cipher Spec Protocol
• One of four TLS specific protocols that use the TLS
Record Protocol
• Is the simplest
• Consists of a single message which consists of a single
byte with the value 1
• Sole purpose of this message is to cause pending state to
be copied into the current state
• Hence updating the cipher suite in use
 Alert Protocol
Alert messages are
Conveys TLS-related
compressed and
alerts to peer entity
encrypted

If the level is fatal, TSL

immediately terminates
the connection

First byte takes the

value warning (1) or
fatal (2) to convey the Other connections on
severity of the message the same session may
Each message consists continue, but no new
of two bytes: connections on this
session may be
Second byte contains a established
code that indicates the
specific alert
 Handshake Protocol
• Most complex part of TLS
• Is used before any application data are transmitted
• Allows server and client to:

Negotiate Negotiate
Authenticate
encryption and cryptographic
each other
MAC algorithms keys to be used

• Comprises a series of messages exchanged by client and

server
• Exchange has four phases
 Heartbeat Protocol
• A periodic signal generated by hardware or software to
indicate normal operation or to synchronize other parts of a
system
• Typically used to monitor the availability of a protocol entity
• Defined in 2012 in RFC 6250
• Runs on top of the TLS Record Protocol
• Use is established during Phase 1 of the Handshake Protocol
• Each peer indicates whether it supports heartbeats
• Serves two purposes:
• Assures the sender that the recipient is still alive
• Generates activity across the connection during idle periods
 SSL/TLS Attacks

Attacks on the record

Attacks on the and application data
Handshake Protocol protocols
Four general
categories:

Attacks on the PKI Other attacks

 HTTPS
(HTTP over SSL)
• Combination of HTTP and SSL to implement secure
communication between a Web browser and a Web server
• Built into all modern Web browsers
• Search engines do not support HTTPS
• URL addresses begin with https://

• Documented in RFC 2818, HTTP Over TLS

• Agent acting as the HTTP client also acts as the TLS client
• Closure of an HTTPS connection requires that TLS close
the connection with the peer TLS entity on the remote side,
which will involve closing the underlying TCP connection
 IP Security (IPsec)
• Various application security mechanisms
• S/MIME, Kerberos, SSL/HTTPS
•Security concerns cross protocol layers
• Would like security implemented by the
network for all applications
• Authentication and encryption security
features included in next-generation IPv6
• Also usable in existing IPv4
 Benefits of IPsec
• When implemented in a firewall or router, it
provides strong security to all traffic crossing the
perimeter
• In a firewall it is resistant to bypass
• Below transport layer, hence transparent to
applications
• Can be transparent to end users
• Can provide security for individual users
• Secures routing architecture
Provides two main
functions:
The Scope of IPsec
• A combined VPNs want
authentication/encryption both
function called authentication
Encapsulating Security
Payload (ESP) and
• Key exchange function encryption

Also an Specification is
authentication-only quite complex
function, • Numerous RFC’s
implemented using 2401/4302/
4303/4306
an Authentication
Header (AH)
• Because message
authentication is provided
by ESP, the use of AH is
included in IPsecv3 for
backward compatibility
but should not be used in
new applications
 Security Associations
• A one-way relationship
between sender and receiver Defined by 3
that affords security for
traffic flow
parameters:
• If a peer relationship is needed Security Parameter Index
for two-way secure exchange (SPI)
then two security associations
are required
IP Destination Address
• Is uniquely identified by the
Destination Address in the
IPv4 or IPv6 header and the Protocol Identifier
SPI in the enclosed extension
header (AH or ESP)
Transport and Tunnel Modes
Transport Mode Tunnel Mode
• Provides protection to the entire
• Extends to the payload of an IP IP packet
packet
• The entire original packet
• Typically used for end-to-end travels through a tunnel from
communication between two one point of an IP network to
hosts another
• ESP encrypts and optionally • Used when one or both ends of
authenticates the IP payload a security association are a
but not the IP header security gateway
• A number of hosts on networks
behind firewalls may engage in
secure communications without
implementing IPsec
 Summary
• Secure E-mail and
S/MIME • HTTPS
• MIME • Connection institution
• S/MIME • Connection closure
• DomainKeys • IPv4 and IPv6
identified mail security
• Internet mail architecture • IP security overview
• DKIM strategy • The scope of IPsec
• Security associations
• SSL and TLS • Encapsulating security
• TLS architecture payload
• TLS protocols • Transport and tunnel
• TLS attacks modes
• SSL/TLS attacks