Chapter 7:

Cryptographic Systems

CCNA Security

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 Chapter 7: Objectives
In this chapter you will:
 Describe the requirements of secure communications including integrity, authentication, and confidentiality.
 Describe cryptography and provide an example.
 Describe cryptanalysis and provide an example.
 Describe cryptology and provide an example.
 Describe the importance and functions of cryptographic hashes.
 Describe the features and functions of the MD5 algorithm and of the SHA-1 algorithm.
 Describe how to enable authenticity with HMAC.
 Describe the components of key management.
 Describe the mechanisms used to ensure data confidentiality.
 Describe the function of the DES algorithms.
 Describe the function of the 3DES algorithm.
 Describe the function of the AES algorithm.
 Describe the function of the Software Encrypted Algorithm (SEAL) and the Rivest ciphers (RC) algorithms.
 Describe the function of the DH algorithm and its supporting role to DES, 3DES, and AES.
 Explain the differences between symmetric and asymmetric encryptions and their intended applications.
 Explain the functionality of digital signatures.
 Describe the function of the RSA algorithm.
 Describe the principles behind a public key infrastructure (PKI).
 Describe the various PKI standards.
 Describe the role of CAs and the digital certificates that they issue in a PKI.
 Describe the characteristics of digital certificates and CAs.

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 Chapter 7
7.0 Introduction
7.1 Cryptographic Services
7.2 Basic Integrity and Authenticity
7.3 Confidentiality
7.4 Public Key Cryptography
7.5 Summary

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 7.1 Cryptographic Services

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 Securing Communications
Authentication, Integrity, and Confidentiality
 To ensure secure communications, the
network administrator’s primary goal is
to secure the network’s infrastructure,
including routers, switches, servers,
and hosts.
 A network LAN can be secured
through:
• Device hardening
• AAA access control
• Firewall features
• IPS implementations
 How is network traffic protected when
traversing the public Internet? By using
cryptographic methods.

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 Securing Communications
Authentication, Integrity, and Confidentiality Cont.
Secure communications
necessitates three primary
objectives:
• Authentication - Guarantees that
Authentication
the message is not a forgery and
does actually come from whom it
states.
• Integrity - Guarantees that no one
intercepted the message and
altered it; similar to a checksum
function in a frame. Integrity
• Confidentiality - Guarantees that
if the message is captured, it
cannot be deciphered.

Confidentiality
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Securing Communications
Authentication
 Authentication guarantees that
the message:
• Is not a forgery.
• Does actually come from who it
states it comes from.
 Authentication is similar to a
secure PIN for banking at an
ATM.
• The PIN should only be known
to the user and the financial
institution.
• The PIN is a shared secret that
helps protect against forgeries.

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Securing Communications
Authentication Cont.
 Data nonrepudiation is a similar service that allows the sender
of a message to be uniquely identified.
 This means that a sender/device cannot deny having been the
source of that message. It cannot repudiate, or refute, the
validity of a message sent.

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Securing Communications
Data Integrity
 Data integrity ensures that messages
are not altered in transit. The receiver
can verify that the received message is
identical to the sent message and that
no manipulation occurred.
 European nobility ensured the data
integrity by creating a wax seal to close
an envelope.
• The seal was often created using a
signet ring.
• An unbroken seal on an envelope
guaranteed the integrity of its contents.
• It also guaranteed authenticity based
on the unique signet ring impression.

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Securing Communications
Data Confidentiality Cont.
 Data confidentiality ensures
privacy so that only the receiver
can read the message.
 Encryption is the process of
scrambling data so that it
cannot be read by unauthorized
parties.
• Readable data is called
plaintext, or cleartext.
• Encrypted data is called
ciphertext.
 A key is required to encrypt and
decrypt a message. The key is
the link between the plaintext
and ciphertext.
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Cryptography
Creating Ciphertext
 Authentication, integrity, and confidentiality are components of
cryptography.
 Cryptography is both the practice and the study of hiding
information.
 It has been used for centuries to protect secret documents.
Today, modern day cryptographic methods are used in multiple
ways to ensure secure communications.

Authentication Integrity Confidentiality

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Cryptography
Creating Ciphertext Cont.
 Encryption methods uses a specific algorithm, called a
cipher, to encrypt and decrypt messages.
 A cipher is a series of well-defined steps that can be
followed as a procedure when encrypting and decrypting
messages.
 There are several methods of creating cipher text:
• Transposition
• Substitution
• One-time pad

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Cryptography
Creating Ciphertext Cont.
 Cryptography is both the practice and the study of hiding
information.
 Cryptography is used to ensure the protection of data when that
data might be exposed to untrusted parties.
 Cryptographic services are the foundation for many security
implementations
 Over the centuries, various cipher methods, physical devices, and
aids have been used to encrypt and decrypt text:
• Scytale
• Caesar cipher
• Vigenère Cipher
• Jefferson’s encryption device
• German Enigma machine
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Creating Cipher Text
Creating Ciphertext Cont.
Scytale
 Earliest cryptography method was
used by the Spartans in ancient
Greece.
 It is a rod used as an aid for a
transposition cipher. The sender and
receiver had identical rods (scytale)
on which to wrap a transposed
messaged.

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Cryptography
Creating Ciphertext Cont.
Caesar Cipher
 When Julius Caesar sent
messages to his generals, he did
not trust his messengers.
 Caesar encrypted his messages
by replacing every letter:
• A with a D
• B with an E
• and so on
 His generals knew the “shift by
3” rule and could decipher his
messages.

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Cryptography
Vigenère Cipher
Vigenère Cipher
 In 1586, Frenchman Blaise de
Vigenère described a
polyalphabetic system of
encryption. It became known as
the Vigenère Cipher.
 Based on the Caesar cipher, it
encrypted plaintext using a multi-
letter key. It is also referred to as
an autokey cipher.

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Cryptography
Vigenère Cipher Cont.
a b c d e f g h i j k l m n o p q r s t u v w x y z
A a b c d e f g h i j k l m n o p q r s t u v w x y z
B b c d e f g h i j k l m n o p q r s t u v w x y z a
C c d e f g h i j k l m n o p q r s t u v w x y z a b
D d e f g h i j k l m n o p q r s t u v w x y z a b c
E e f g h i j k l m n o p q r s t u v w x y z a b c d
F f g h i j k l m n o p q r s t u v w x y z a b c d e
G g h i j k l m n o p q r s t u v w x y z a b c d e f
H h i j k l m n o p q r s t u v w x y z a b c d e f g
I i j k l m n o p q r s t u v w x y z a b c d e f g h
J j k l m n o p q r s t u v w x y z a b c d e f g h i
K k l m n o p q r s t u v w x y z a b c d e f g h i j
L l m n o p q r s t u v w x y z a b c d e f g h i j k
M m n o p q r s t u v w x y z a b c d e f g h i j k l
N n o p q r s t u v w x y z a b c d e f g h i j k l m
O o p q r s t u v w x y z a b c d e f g h i j k l m n
P p q r s t u v w x y z a b c d e f g h i j k l m n o
Q q r s t u v w x y z a b c d e f g h i j k l m n o p
R r s t u v w x y z a b c d e f g h i j k l m n o p q
S s t u v w x y z a b c d e f g h i j k l m n o p q r
T t u v w x y z a b c d e f g h i j k l m n o p q r s
U u v w x y z a b c d e f g h i j k l m n o p q r s t
V v w x y z a b c d e f g h i j k l m n o p q r s t u
W w x y z a b c d e f g h i j k l m n o p q r s t u v
X x y z a b c d e f g h i j k l m n o p q r s t u v w
Y y z a b c d e f g h i j k l m n o p q r s t u v w x
Z z a b c d e f g h i j k l m n o p q r s t u v w x y
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Cryptography
Creating Ciphertext Cont.
Jefferson’s Encryption Device
 Thomas Jefferson, the third
president of the United States,
invented an encryption system
that was believed to have been
used when he served as
secretary of state from 1790 to
1793.

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Cryptography
Creating Ciphertext Cont.
German Enigma Machine
 Arthur Scherbius invented the Enigma
in 1918 and sold it to Germany. It
served as a template for the machines
that all the major participants in World
War II used.
 It was estimated that if 1,000
cryptanalysts tested four keys per
minute, all day, everyday, it would take
1.8 billion years to try them all.
 Germany knew their ciphered
messages could be intercepted by the
allies, but never thought they could be
deciphered.
http://users.telenet.be/d.rijmenants/en/enigma.htm

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Cryptography
Transposition Ciphers
 In transposition ciphers, no letters are replaced; they are simply
rearranged.
 For example: Spell it backwards.
 Modern encryption algorithms, such as the Data Encryption
Standard (DES) and 3DES, still use transposition as part of the
algorithm.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 22
Cryptography
Transposition Ciphers - Rail Fence Cipher
FKTTAW
1 Solve the ciphertext. LNESATAKTAN
AATCD

Ciphered text

F...K...T...T...A...W.
2 .L.N.E.S.A.T.A.K.T.A.N
Use a rail fence cipher and a
key of 3. ..A...A...T...C...D...

FLANK EAST
3 The cleartext message. ATTACK AT DAWN

Cleartext

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Cryptography
Substitution Ciphers

 Substitution ciphers substitute one letter for another. In their

simplest form, substitution ciphers retain the letter frequency of
the original message.
 Examples include:
• Caesar Cipher
• Vigenère Cipher

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Cryptography
Substitution Ciphers - Encoding using the
Caesar Cipher
FLANK EAST
1 The cleartext message. ATTACK AT DAWN

Cleartext

2 Encode using a key of 3. Therefore, A becomes a D, B an E, …

A B C D E F G H I J K L M N O P Q R S T U V W X Y Z

A B C D E F G H I J K L M N O P Q R S T U V W X Y Z A B C

IODQN HDVW
3 The encrypted message becomes … DWWDFN DW GDZQ

Ciphered text

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Cryptography
Substitution Ciphers - Caesar Cipher Disk
1
FLANK EAST The cleartext message would be
ATTACK AT DAWN encoded using a key of 3.
Cleartext

2 Shifting the
inner wheel by
3, the A
becomes D, B
becomes E,
and so on.

3
IODQN HDVW The cleartext message appears as
DWWDFN DW GDZQ follows using a key of 3.

Ciphered text

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 27
Cryptography
Substitution Ciphers - Vigenère Cipher
 The Vigenère cipher is based on the Caesar cipher, except that it
encrypts text by using a different polyalphabetic key shift for every
plaintext letter.
• The different key shift is identified using a shared key between
sender and receiver.
• The plaintext message can be encrypted and decrypted using the
Vigenère Cipher Table.
 For example:
• A sender and receiver have a shared secret key: SECRETKEY.
• The sender then uses the key to encode: FLANK EAST ATTACK
AT DAWN.

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 A B C D E F G H I J K L M N O P Q R S T U V W X Y Z
A a b c d e f g h i j k l m n o p q r s t u v w x y z
B b c d e f g h i j k l m n o p q r s t u v w x y z a
C c d e f g h i j k l m n o p q r s t u v w x y z a b
D d e f g h i j k l m n o p q r s t u v w x y z a b c
E e f g h i j k l m n o p q r s t u v w x y z a b c d
F f g h i j k l m n o p q r s t u v w x y z a b c d e
G g h i j k l m n o p q r s t u v w x y z a b c d e f
H h i j k l m n o p q r s t u v w x y z a b c d e f g
I i j k l m n o p q r s t u v w x y z a b c d e f g h
J j k l m n o p q r s t u v w x y z a b c d e f g h i
K k l m n o p q r s t u v w x y z a b c d e f g h i j
L l m n o p q r s t u v w x y z a b c d e f g h i j k
M m n o p q r s t u v w x y z a b c d e f g h i j k l
N n o p q r s t u v w x y z a b c d e f g h i j k l m
O o p q r s t u v w x y z a b c d e f g h i j k l m n
P p q r s t u v w x y z a b c d e f g h i j k l m n o
Q q r s t u v w x y z a b c d e f g h i j k l m n o p
R r s t u v w x y z a b c d e f g h i j k l m n o p q
S s t u v w x y z a b c d e f g h i j k l m n o p q r
T t u v w x y z a b c d e f g h i j k l m n o p q r s
U u v w x y z a b c d e f g h i j k l m n o p q r s t
V v w x y z a b c d e f g h i j k l m n o p q r s t u
W w x y z a b c d e f g h i j k l m n o p q r s t u v
X x y z a b c d e f g h i j k l m n o p q r s t u v w
Y y z a b c d e f g h i j k l m n o p q r s t u v w x
Z z a b c d e f g h i j k l m n o p q r s t u v w x y

F L A N K E A S T A T T A C K A T D A W N
S E C R E T K E Y S E C R E T K E Y S E C
X P C E O X K U R S X V R G D K X B S A P
Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 29
 A B C D E F G H I J K L M N O P Q R S T U V W X Y Z
A a b c d e f g h i j k l m n o p q r s t u v w x y z
B b c d e f g h i j k l m n o p q r s t u v w x y z a
C
D
c
d
d
e
e
f
f
g
g
h
h
i
i
j
j
k
k
l
l
m
To Decrypt ….
m
n
n
o
o
p
p
q
q
r
r
s
s
t
t
u
u
v
v
w
w
x
x
y
y
z
z
a
a
b
b
c
E e f g h i j k l m n o p q r s t u v w x y z a b c d
F f g h i j k l m n o p q r s t u v w x y z a b c d e
G g h i j k l m n o p q r s t u v w x y z a b c d e f
H h i j k l m n o p q r s t u v w x y z a b c d e f g
I i j k l m n o p q r s t u v w x y z a b c d e f g h
J j k l m n o p q r s t u v w x y z a b c d e f g h i
K k l m n o p q r s t u v w x y z a b c d e f g h i j
L l m n o p q r s t u v w x y z a b c d e f g h i j k
M m n o p q r s t u v w x y z a b c d e f g h i j k l
N n o p q r s t u v w x y z a b c d e f g h i j k l m
O o p q r s t u v w x y z a b c d e f g h i j k l m n
P p q r s t u v w x y z a b c d e f g h i j k l m n o
Q q r s t u v w x y z a b c d e f g h i j k l m n o p
R r s t u v w x y z a b c d e f g h i j k l m n o p q
S s t u v w x y z a b c d e f g h i j k l m n o p q r
T t u v w x y z a b c d e f g h i j k l m n o p q r s
U u v w x y z a b c d e f g h i j k l m n o p q r s t
V v w x y z a b c d e f g h i j k l m n o p q r s t u
W w x y z a b c d e f g h i j k l m n o p q r s t u v
X x y z a b c d e f g h i j k l m n o p q r s t u v w
Y y z a b c d e f g h i j k l m n o p q r s t u v w x
Z z a b c d e f g h i j k l m n o p q r s t u v w x y

S E C R E T K E Y S E C R E T K E Y S E C
X P C E O X K U R S X V R G D K X B S A P
F L A N K E A S T A T T A C K A T D A W N
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 A B C D E F G H I J K L M N O P Q R S T U V W X Y Z
A a b c d e f g h i j k l m n o p q r s t u v w x y z
B b c d e f g h i j k l m n o p q r s t u v w x y z a
C c d e f g h i j k l m n o p q r s t u v w x y z a b
D d e f g h i j k l Decrypt the following ….
m n o p q r s t u v w x y z a b c
E e f g h i j k l m n o p q r s t u v w x y z a b c d
F f g h i j k l m n o p q r s t u v w x y z a b c d e
G g h i j k l m n o p q r s t u v w x y z a b c d e f
H h i j k l m n o p q r s t u v w x y z a b c d e f g
I i j k l m n o p q r s t u v w x y z a b c d e f g h
J j k l m n o p q r s t u v w x y z a b c d e f g h i
K k l m n o p q r s t u v w x y z a b c d e f g h i j
L l m n o p q r s t u v w x y z a b c d e f g h i j k
M m n o p q r s t u v w x y z a b c d e f g h i j k l
N n o p q r s t u v w x y z a b c d e f g h i j k l m
O o p q r s t u v w x y z a b c d e f g h i j k l m n
P p q r s t u v w x y z a b c d e f g h i j k l m n o
Q q r s t u v w x y z a b c d e f g h i j k l m n o p
R r s t u v w x y z a b c d e f g h i j k l m n o p q
S s t u v w x y z a b c d e f g h i j k l m n o p q r
T t u v w x y z a b c d e f g h i j k l m n o p q r s
U u v w x y z a b c d e f g h i j k l m n o p q r s t
V v w x y z a b c d e f g h i j k l m n o p q r s t u
W w x y z a b c d e f g h i j k l m n o p q r s t u v
X x y z a b c d e f g h i j k l m n o p q r s t u v w
Y y z a b c d e f g h i j k l m n o p q r s t u v w x
Z z a b c d e f g h i j k l m n o p q r s t u v w x y

T C P I P T C P I P T C P I P T C P I P T
V E C I H X E J Z X M A
C C N A S E C U R I T Y
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Cryptography
One-Time Pad Ciphers
 In 1917, Gilbert Vernam, an AT&T Bell Labs engineer, invented
and patented the stream cipher and later co-invented the one-
time pad cipher.
• Vernam proposed a teletype cipher in which a prepared key
consisting of an arbitrarily long, non-repeating sequence of
numbers was kept on paper tape.
• It was then combined character by character with the plaintext
message to produce the ciphertext.
• To decipher the ciphertext, the same paper tape key was again
combined character by character, producing the plaintext.
 Each tape was used only once,; hence the name one-time pad.
As long as the key tape does not repeat or is not reused, this type
of cipher is immune to cryptanalytic attack, because the available
ciphertext does not display the pattern of the key.

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Cryptography
One-Time Pad Ciphers

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Cryptography
One-Time Pad Ciphers Cont.
 Several difficulties are inherent in using one-time pads in the real
world.
• Key distribution is challenging.
• Creating random data is challenging and if a key is used more than
once, it becomes easier to break.
 Computers, because they have a mathematical foundation, are
incapable of creating true random data.
 RC4 is a one-time pad cipher that is widely used on the Internet.
However, because the key is generated by a computer, it is not
truly random.

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Cryptanalysis
Cracking Code

 The practice and study of

determining the meaning of
encrypted information
(cracking the code),
without access to the
shared secret key.
 Been around since
cryptography.

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Cryptanalysis
Methods for Cracking Code
 Brute-Force Method
 Ciphertext-Only Method
 Known-Plaintext Method
 Chosen-Plaintext Method
 Chosen-Ciphertext Method
 Meet-in-the-Middle Method

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Cryptanalysis
Methods for Cracking Code - Brute-Force Attack

 An attacker tries every possible key with the decryption algorithm

knowing that eventually one of them will work. All encryption
algorithms are vulnerable to this attack.
 The objective of modern cryptographers is to have a keyspace
large enough that it takes too much time (money) to accomplish a
brute-force attack.
 For example: The best way to crack Caesar cipher-encrypted
code is to use brute force.
• There are only 25 possible rotations.
• Therefore, it is not a big effort to try all possible rotations and see
which one returns something that makes sense.

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Cryptanalysis
Methods for Cracking Code - Brute-Force Attack

 On average, a brute-force attack succeeds about 50 percent of the way

through the keyspace, which is the set of all possible keys.
 A DES cracking machine recovered a 56-bit DES key in 22 hours using
brute force.
 It is estimated it would take 149 trillion years to crack an AES key using
the same method.

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Cryptanalysis
Methods for Cracking Code - Ciphertext-Only Attack

 An attacker has:
• The ciphertext of several messages, all of which have been
encrypted using the same encryption algorithm, but the attacker
has no knowledge of the underlying plaintext.
• The attacker could use statistical analysis to deduce the key.
 These kinds of attacks are no longer practical, because modern
algorithms produce pseudorandom output that is resistant to
statistical analysis.

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Cryptanalysis
Methods for Cracking Code - Known-Plaintext Attack

 An attacker has:
• Access to the ciphertext of several messages.
• Knowledge (underlying protocol, file type, or some characteristic
strings) about the plaintext underlying that ciphertext.
 The attacker uses a brute-force attack to try keys until decryption
with the correct key produces a meaningful result.
 Modern algorithms with enormous keyspaces make it unlikely for
this attack to succeed, because, on average, an attacker must
search through at least half of the keyspace to be successful.

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Cryptanalysis
Methods for Cracking Code - Chosen-Plaintext Attack

 An attacker chooses which data the encryption device encrypts

and observes the ciphertext output. A chosen-plaintext attack is
more powerful than a known-plaintext attack, because the chosen
plaintext might yield more information about the key.
 This attack is not very practical, because it is often difficult or
impossible to capture both the ciphertext and plaintext.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 41
Cryptanalysis
Methods for Cracking Code - Chosen-Ciphertext Attack

 An attacker chooses different ciphertext to be decrypted and has

access to the decrypted plaintext. With the pair, the attacker can
search through the keyspace and determine which key decrypts
the chosen ciphertext in the captured plaintext.
 This attack is analogous to the chosen-plaintext attack.
• Like the chosen-plaintext attack, this attack is not very practical.
• Again, it is difficult or impossible for the attacker to capture both the
ciphertext and plaintext.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 42
Cryptanalysis
Methods for Cracking Code - Meet-in-the-Middle
 The meet-in-the-middle attack is a known plaintext attack.
 The attacker knows that a portion of the plaintext and the
corresponding ciphertext.
 The plaintext is encrypted with every possible key, and the results
are stored. The ciphertext is then decrypted using every key, until
one of the results matches one of the stored values.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 43
Cryptanalysis
Cracking Code Example
 The best way to crack the code is to
use brute force.
 Because there are only 25 possible
rotations, the effort is relatively small
to try all possible rotations and see
which one returns something that
makes sense.
 A more scientific approach is to use
the fact that some characters in the
English alphabet are used more
often than others.
 This method is called frequency
analysis.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 44
Cryptanalysis
Cracking Code Example- Frequency Analysis Method

 The English alphabet is used more

often than others.
• E, T, and A are the most popular
letters.
• J, Q, X, and Z are the least
popular. Ciphered Text
 Caesar ciphered message:
• The letter D appears six times.
• The letter W appears four times. FLANK EAST
ATTACK AT DAWN
• Therefore, it is probable that they
represent the more popular letters.
Cleartext
 In this case, D represents the letter A,
and W represents the letter T.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 45
Cryptology
Making and Breaking Secret Codes

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 46
Cryptology
Making and Breaking Secret Codes Cont.
 Cryptology is the science of making and breaking secret codes. It
combines cryptography (development and use of codes), and
cryptanalysis, (breaking of those codes).
 There is a symbiotic relationship between the two disciplines,
because each makes the other one better.
• National security organizations employ members of both disciplines
and put them to work against each other.
 There have been times when one of the disciplines has been
ahead of the other.
• Currently, it is believed that cryptographers have the edge.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 47
Cryptology
Cryptanalysis
 Ironically, it is impossible to prove
an algorithm secure. It can only be
proven that it is not vulnerable to
known cryptanalytic attacks.
 There is a need for
mathematicians, scholars, and
security forensic experts to keep
trying to break the encryption
methods.
 Cryptanalysis are most used
employed by:
• Governments in military and
diplomatic surveillance.
• Enterprises in testing the strength of
security procedures.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 48
Cryptology
The Secret Is in the Keys
Authentication, integrity, and data confidentiality are implemented in
many ways using various protocols and algorithms. Choice
depends on the security level required in the security policy.

Integrity Authentication Confidentiality

Common
cryptographic HMAC-MD5 DES (weaker)
MD5 (weaker)
hashes, HMAC-SHA-1 3DES
protocols, and SHA (stronger)
RSA and DSA AES (stronger)
algorithms

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 49
Cryptology
The Secret Is in the Keys Cont.
 Security of encryption lies in the secrecy of the keys, not the
algorithm.
 Old encryption algorithms were based on the secrecy of the
algorithm to achieve confidentiality.
 With modern technology, algorithm secrecy no longer matters
since reverse engineering is often simple; therefore, public-
domain algorithms are often used. Now, successful decryption
requires knowledge of the keys.
 How can the keys be kept secret?

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 50
 7.2 Basic Integrity and
Authenticity

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 51
Cryptographic Hashes
Cryptographic Hash Function
 A hash function takes binary data
(message), and produces a
condensed representation, called a
hash. The hash is also commonly
called a Hash value, Message
digest, or Digital fingerprint.
 Hashing is based on a one-way
mathematical function that is
relatively easy to compute, but
significantly harder to reverse.
 Hashing is designed to verify and
ensure:
• Data integrity
• Authentication

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 52
Cryptographic Hashes
Cryptographic Hash Function Cont.
Cryptographic hash function is applied in many different situations:
 To provide proof of authenticity when it is used with a symmetric
secret authentication key, such as IP Security (IPsec) or routing
protocol authentication.
 To provide authentication by generating one-time and one-way
responses to challenges in authentication protocols, such as the
PPP CHAP.
 To provide a message integrity check proof, such as those
accepted when accessing a secure site using a browser.
 To confirm that a downloaded file (e.g., Cisco IOS images) has
not been altered.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 53
Cryptographic Hashes
Cryptographic Hash Function Properties
 Take an arbitrarily length of clear
text data to be hashed.
 Put it through a hash function.
 It produces a fixed length
message digest (hash value).
 H(x) is:
Relatively easy to computer for MD5
SHA-1
any given x.
One way and not reversible.
 If a hash function is hard to invert,
it is considered a one-way hash.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 54
Cryptographic Hashes
Well-Known Hash Functions
 Hash functions are helpful when ensuring data is not changed accidentally, such as by a
communication error.

 Hash functions cannot be used to guard against deliberate changes.

 There is no unique identifying information from the sender in the hashing procedure, so
anyone can compute a hash for any data, as long as they have the correct hash function.

 Hashing is vulnerable to man-in-the-middle attacks and does not provide security to

transmitted data.

 Two well-known hash functions are:

• MD5 with 128-bit digests
• SHA-256 with 256-bit digests

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 55
Integrity with MD5 and SHA-1
Message Digest 5 Algorithm
 MD5 algorithm is a hashing
algorithm that was developed by
Ron Rivest.
 Used in a variety of Internet
applications today.
 A one-way function that makes it
easy to compute a hash from the
given input data, but makes it
unfeasible to compute input data
given only a hash value.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 56
Integrity with MD5 and SHA-1
Secure Hash Algorithm
 U.S. National Institute of
Standards and Technology
(NIST) developed SHA, the
algorithm specified in the Secure
Hash Standard (SHS).
 SHA-1, published in 1994,
corrected an unpublished flaw in
SHA.
 SHA design is very similar to the
MD4 and MD5 hash functions
that Ron Rivest developed.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 57
Integrity with MD5 and SHA-1
Secure Hash Algorithm Cont.
 SHA-1 algorithm takes a message of
less than 2^64 bits in length and
produces a 160-bit message digest.
 Slightly slower than MD5, but the
larger message digest makes it more
secure against brute-force collision
and inversion attacks.
 NIST published four additional hash
functions in the SHA family, each with
longer digests:
• SHA-224 (224 bit)
• SHA-256 (256 bit)
• SHA-384 (384 bit)
• SHA-512 (512 bit)
Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 58
Integrity with MD5 and SHA-1
MD5 Versus SHA-1
MD5 SHA-1

Based on MD4 Based on MD4

Computation involves 64 steps Computation involves 80 steps

Algorithm must process a 128-bit Algorithm must process a 160-bit

buffer buffer

Faster Slower

Less Secure More secure

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 59
Authenticity with HMAC
Keyed-Hash Message Authentication Code
 HMAC (or KHMAC) is a message authentication code (MAC) that
is calculated using a hash function and a secret key.
• HMACs use an additional secret key as input to the hash function
adding authentication to integrity assurance.
• Hash functions are the basis of the protection mechanism of
HMACs.
• The output of the hash function now depends on the input data and
the secret key.
 Authenticity is guaranteed, because only the sender and the
receiver know the secret key.
• Only they can compute the digest of an HMAC function.
• This characteristic defeats man-in-the-middle attacks and provides
authentication of the data origin.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 60
Authenticity with HMAC
Keyed-Hash Message Authentication Code Cont.
 The cryptographic strength of the
HMAC depends on the:
• Cryptographic strength of the
underlying hash function.
• Size and quality of the key.
• Size of the hash output length
in bits.
 Cisco technologies use two well-
known HMAC functions:
• Keyed MD5 or HMAC-MD5 is
based on the MD5 hashing
algorithm.
• Keyed SHA-1 or HMAC-SHA-1
is based on the SHA-1 hashing
algorithm.
Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 61
Authenticity with HMAC
HMAC Operation
Data Received Data
Pay to Terry Smith $100.00 Pay to Terry Smith $100.00
Secret Secret
One Hundred and xx/100 Dollars Key One Hundred and xx/100 Dollars
Key

HMAC HMAC
(Authenticated 4ehIDx67NMop9 (Authenticated 4ehIDx67NMop9
Fingerprint) Fingerprint)

Pay to Terry Smith $100.00 If the generated HMAC matches the

One Hundred and xx/100 Dollars sent HMAC, then integrity and
authenticity have been verified.
4ehIDx67NMop9
If they don’t match, discard the
message.
Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 62
Authenticity with HMAC
HMAC and Cisco Products
 Cisco products use hashing for entity
authentication, data integrity, and
data authenticity purposes.
 For example:
• Authenticating routing protocol
updates.
• IPsec VPNs use MD5 and SHA-1 in
HMAC mode, to provide packet
integrity and authenticity.
• IOS images downloaded from
Cisco.com have an MD5-based
checksum to check the integrity of
downloaded images.
• TACACS+ uses an MD5 hash as
the key to encrypt the session.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 63
Key Management
Characteristics of Key Management
 Often considered the most difficult part of designing a
cryptosystem.
 There are several essential characteristics of key management to
consider:
• Key generation
• Key verification
• Key storage
• Key exchange
• Key revocation and destruction

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 64
Key Management
Characteristics of Key Management Cont.
 Key Generation
• Caesar chose the key of his cipher and the Sender/Receiver chose
a shared secret key for the Vigenère cipher.
• Modern cryptographic system key generation is usually automated.
 Key Verification
• Almost all cryptographic algorithms have some weak keys that
should not be used (e.g., Caesar cipher ROT 0 or ROT 25).
• With the help of key verification procedures, these keys can be
regenerated if they occur.
 Key Storage - Modern cryptographic system store keys in
memory.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 65
Key Management
Characteristics of Key Management Cont.
 Key Exchange
• Key management procedures should provide a secure key
exchange mechanism over an untrusted medium.
 Key Revocation and Destruction
• Revocation notifies all interested parties that a certain key has been
compromised and should no longer be used.
• Destruction erases old keys in a manner that prevents malicious
attackers from recovering them.
 Two terms that are used to describe keys are:
• Key size - The measure in bits; also called the key length.
• Keyspace - This is the number of possibilities that can be
generated by a specific key length.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 66
Key Management
Characteristics of Key Management Cont.
 The key length is the measure in bits and the keyspace is the
number of possibilities that can be generated by a specific key
length.
 As key lengths increase, keyspace increases exponentially:
• 22 key = a keyspace of 4
• 23 key = a keyspace of 8
• 24 key = a keyspace of 16
• 240 key = a keyspace of 1,099,511,627,776

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 67
Key Management
The Keyspace
 Adding one bit to a key doubles the keyspace.
 For each bit added to the DES key, the attacker would require
twice the amount of time to search the keyspace.
 Longer keys are more secure but are also more resource
intensive and can affect throughput.

DES Key Length Keyspace # of Possible Keys

56 bit 25 72,000,000,000,000,000
57 bit 257 144,000,000,000,000,000
58 bit 258 288,000,000,000,000,000
59 bit 259 576,000,000,000,000,000
60 bit 260 1,152,000,000,000,000,000

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 68
Key Management
Types of Cryptographic Keys
 Symmetric keys that can be exchanged between two routers
supporting a VPN.
 Asymmetric keys that used in secure HTTPS applications.
 Digital signatures that used when connecting to a secure website.
 Hash keys that used in symmetric and asymmetric key
generation, digital signatures, and other types of applications.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 69
Key Management
Choosing Cryptographic Keys
 Performance is another issue
that can influence the choice of
a key length.
 An administrator must find a
good balance between the
speed and protective strength
of an algorithm.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 71
 7.3 Confidentiality

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 72
Encryption
Cryptographic Encryption
Cryptographic encryption can provide confidentiality at several
layers of the OSI model by incorporating various tools and
protocols:
• Proprietary link-encrypting devices provide data link layer
confidentiality.
• Network layer protocols, such as the IPsec protocol suite, provide
network layer confidentiality.
• Protocols, such as Secure Sockets Layer (SSL) or Transport Layer
Security (TLS), provide session layer confidentiality.
• Secure email, secure database session (Oracle SQL*net), and
secure messaging (Lotus Notes sessions) provide application layer
confidentiality.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 73
Encryption
Symmetric Encryption Algorithms
Symmetric encryption algorithms characteristics include:
• Symmetric encryption algorithms are best known as shared-secret key
algorithms.
• The usual key length is 80 to 256 bits.
• A sender and receiver must share a secret key.
• They are usually quite fast (wire speed), because these algorithms are
based on simple mathematical operations.
• Examples of symmetric encryption algorithms are DES, 3DES, AES, IDEA,
RC2/4/5/6, and Blowfish.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 74
Encryption
Asymmetric Encryption Algorithms Cont.
Asymmetric encryption algorithms characteristics include:
• Asymmetric encryption algorithms are best known as public key algorithms.
• The usual key length is 512 to 4,096 bits.
• A sender and receiver do not share a secret key.
• These algorithms are relatively slow, because they are based on difficult
computational algorithms.
• Examples: RSA, ElGamal, elliptic curves, and DH.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 75
Encryption
Symmetric Encryption Algorithms Cont.
 Symmetric encryption algorithms, also called shared secret-key
algorithms, use the same pre-shared secret key to encrypt and
decrypt data. The pre-shared key is known by the sender and
receiver before any encrypted communications begins.
 Because both parties are guarding a shared secret, the
encryption algorithms used can have shorter key lengths. Shorter
key lengths mean faster execution.
 For this reason symmetric algorithms are generally much less
computationally intensive than asymmetric algorithms.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 76
Encryption
Symmetric Encryption Techniques
There are two types of encryption method used:
• Block Ciphers
• Stream Ciphers

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Encryption
Symmetric Encryption Techniques Cont.
 Block ciphers transform a fixed-length block of plaintext into a
common block of ciphertext of 64 or 128 bits.
• Block size refers to how much data is encrypted at any one time.
• The key length refers to the size of the encryption key that is used.
• This ciphertext is decrypted by applying the reverse transformation
to the ciphertext block, using the same secret key.
 Common block ciphers include:
• DES with a 64-bit block size
• AES with a 128-bit block size
• RSA with a variable block size

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 78
Encryption
Symmetric Encryption Techniques Cont.
 Stream ciphers encrypt plaintext one byte or one bit at a time.
• Think of it like a block cipher with a block size of one bit.
• The Vigenère cipher is an example of a stream cipher.
• Can be much faster than block ciphers, and generally do not
increase the message size.
 Common stream ciphers include:
• A5 used to encrypt GSM cell phone communications.
• RC4 cipher.
• DES can also be used in stream cipher mode.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 79
Encryption
Choosing an Encryption Algorithm
 Is the algorithm trusted by the cryptographic community?
Algorithms that have been resisting attacks for a number of years
are preferred.
 Does the algorithm adequately protects against brute-force
attacks? With the appropriate key lengths, these attacks are
usually considered unfeasible.
 Does the algorithm support variable and long key lengths?
 Does the algorithm have export or import restrictions?

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 80
Encryption
Choosing an Encryption Algorithm Cont.

DES 3DES AES

Is the algorithm trusted by the Been replaced by

Yes Verdict is still out
cryptographic community? 3DES

Does the algorithm adequately

No Yes Yes
protect against brute-force attacks?

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 81
Data Encryption Standard
DES Symmetric Encryption
 The most popular symmetric encryption standard.
• Developed by IBM
• Thought to be unbreakable in the 1970s
• Shared keys enable the encryption and decryption
 DES converts blocks of 64-bits of clear text into ciphertext by
using an encryption algorithm.
• The decryption algorithm on the remote end restores ciphertext to
clear text.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 82
Data Encryption Standard
DES Operation
 ECB mode serially encrypts
each 64-bit plaintext block
using the same 56-bit key.
 If two identical plaintext blocks
are encrypted using the same
key, their ciphertext blocks are
the same.
 Therefore, an attacker could
identify similar or identical
traffic flowing through a
communications channel.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 83
Data Encryption Standard
DES Operation Cont.
 CBC mode, each 64-bit
plaintext block is XORed
bitwise with the previous
ciphertext block and then
is encrypted using the
DES key.
 The encryption of each
block depends on
previous blocks.
 Encryption of the same
64-bit plaintext block can
result in different
ciphertext blocks.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 84
Data Encryption Standard
DES Operation Cont.
 To encrypt or decrypt more than 64 bits of data, DES uses two
common stream cipher modes:
• Cipher feedback (CFB), which is similar to CBC and can
encrypt any number of bits, including single bits or single
characters.
• Output feedback (OFB) generates keystream blocks, which are
then XORed with the plaintext blocks to get the ciphertext.
 The cipher uses previous ciphertext and the secret key to
generate a pseudo-random stream of bits, which only the
secret key can generate.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 85
Data Encryption Standard
DES Summary
 Because of its short key length, DES is considered a good
protocol to protect data for a very short time.
• 3DES is a better choice to protect data, because it has an algorithm
that is very trusted and has higher security strength.
 Recommendations:
• Change keys frequently to help prevent brute-force attacks.
• Use a secure channel to communicate the DES key from the
sender to the receiver.
• Consider using DES in CBC mode.
• Test a key to see if it is a weak key before using it.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 86
3DES
Improving DES with 3DES
 3DES is 256 times stronger than DES.
 It takes a 64-bit block of data and performs three DES operations
in sequence:
• Encrypts, decrypts, and encrypts.
• Requires additional processing time.
• Can use 1, 2, or 3 different keys (when used with only one key, it is
the same as DES).
 3DES software is subject to U.S. export laws.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 87
3DES
Improving DES with 3DES Cont.

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3DES
3DES Operation
3DES Encryption

3DES Decryption

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 89
Advanced Encryption Standard
AES Origins
 1997, the AES initiative was announced, and the public was
invited to propose encryption schemes to replace DES.
 After a five-year standardization process in which 15 competing
designs were presented and evaluated, the U.S. National Institute
of Standards and Technology (NIST) selected the Rijndael block
cipher as the AES algorithm..
• Based on the Rijndael (“Rhine dahl”) algorithm.
• It uses keys with a length of 128, 192, or 256 bits to encrypt blocks
with a length of 128, 192, or 256 bits.
• All 9 combinations of key length and block length are possible.
 AES is now available in the latest Cisco router images that have
IPsec DES/3DES functionality.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 90
Advanced Encryption Standard
AES Summary
 AES was selected to replace DES for a number of reasons:
• The key length of AES makes the key much stronger than DES.
• AES runs faster than 3DES on comparable hardware.
• AES is more efficient than DES and 3DES on comparable
hardware, usually by a factor of five when it is compared with DES.
• AES is more suitable for high-throughput, low-latency
environments, especially if pure software encryption is used.
 However, AES is a relatively young algorithm and the golden rule
of cryptography states that a mature algorithm is always more
trusted.
 3DES is, therefore, a more trusted choice in terms of strength,
because it has been tested and analyzed for 35 years.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 91
Advanced Encryption Standard
AES Summary Cont.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 92
Alternative Encryption Algorithms
Software-Optimized Encryption Algorithm
 The Software-Optimized Encryption Algorithm (SEAL) is an
alternative algorithm to software-based DES, 3DES, and AES.
• Designed in 1993, it is a stream cipher that uses a 160-bit
encryption key.
• Because it is a stream cipher, data is continuously encrypted and,
therefore, much faster than block ciphers.
• However, it has a longer initialization phase during which a large
set of tables is created using SHA (Secure Hash Algorithm).
 SEAL has a lower impact on the CPU compared to other
software-based algorithms. SEAL support was added to Cisco
IOS Software Release 12.3(7)T.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 93
Alternative Encryption Algorithms
Software-Optimized Encryption Algorithm Cont.

SEAL Scorecard

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Alternative Encryption Algorithms
RC Algorithms
 The RC algorithms were designed all or in part by Ronald Rivest,
who also invented MD5.
 The RC algorithms are widely deployed in many networking
applications because of their favorable speed and variable key-
length capabilities.
 There are several variations of RC algorithms including:
• RC2
• RC4
• RC5
• RC6

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 95
Alternative Encryption Algorithms
RC Algorithms Cont.
RC Algorithms Scorecard

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 96
Diffie-Hellman Key Exchange
Diffie-Hellman Algorithm
 Whitfield Diffie and Martin Hellman invented the Diffie-Hellman
(DH) algorithm in 1976.
 The DH algorithm is the basis of most modern automatic key
exchange methods and is one of the most common protocols
used in networking today.
 DH is not an encryption mechanism
 DH is not typically used to encrypt data.
• It is a method to securely exchange the keys that encrypt data.
• This key can then be used to encrypt subsequent communications
using a symmetric key cipher.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 97
Diffie-Hellman Key Exchange
Diffie-Hellman Algorithm Cont.

 DH is commonly used when data is exchanged using an IPsec

VPN, data is encrypted on the Internet using either SSL or TLS,
or when SSH data is exchanged.
 It is not an encryption mechanism and is not typically used to
encrypt data, because it is extremely slow for any sort of bulk
encryption.
 It is common to encrypt the bulk of the traffic using a symmetric
algorithm and use the DH algorithm to create keys that will be
used by the encryption algorithm.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 98
Diffie-Hellman Key Exchange
Diffie-Hellman Algorithm Cont.
DH Characteristics

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Diffie-Hellman Key Exchange
DH Operation

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Diffie-Hellman Key Exchange
DH Operation Cont.
Alice and Bob DH Key Exchange

Alice Bob
Shared Secret Calc Shared Secret Calc

5, 23 5, 23
6 56mod 23 = 8

 Bob and Alice agree to use a base number g=5 and prime number
p=23.

 Alice chooses a secret integer a=6.

 Alice sends Bob (ga mod p) or 56 mod 23 = 8.
Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 101
Diffie-Hellman Key Exchange
DH Operation Cont.
Modulo
 In computing, the modulo operation finds the remainder of
division of one number by another.
 Given two numbers, X and Y, a modulo N (abbreviated as a mod
N) is the remainder, on division of a by N.
 For instance:
"8 mod 3" would evaluate to 2.
"9 mod 3" would evaluate to 0.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 102
Diffie-Hellman Key Exchange
DH Operation Cont.
Alice and Bob DH Key Exchange
Alice Bob
Shared Secret Calc Shared Secret Calc

5, 23 5, 23
6 56mod 23 = 8

15 515mod 23 = 19

196mod 23 = 2 815mod 23 = 2

 Meanwhile Bob chooses a secret integer b =15.

 Bob sends Alice (ga mod p) or 515 mod 23 = 19.

 Alice computes (xa mod p) or 196 mod 23 = 2.

 Bob computes (xa mod p) or 86 mod 23 = 2.

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Diffie-Hellman Key Exchange
DH Operation Cont.
Alice and Bob DH Key Exchange
Alice Bob
Shared Secret Calc Shared Secret Calc

5, 23 5, 23
6 56mod 23 = 8

15 515mod 23 = 19

196mod 23 = 2 815mod 23 = 2

 The result (2) is the same for both Alice and Bob.
 They will now use this as the secret key for encryption.

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 104
Diffie-Hellman Key Exchange
DH Operation Cont.
Alice and Bob DH Key Exchange
The initial secret integer used by Alice (6) and Bob (15) are very, very
large numbers (1,024 bits).

8 bits = 10101010
1,024 bits =
101010101010101010101010101010101010101010101010101010101010101010101010101010101010
101010101010101010101010101010101010101010101010101010101010101010101010101010101010
101010101010101010101010101010101010101010101010101010101010101010101010101010101010
101010101010101010101010101010101010101010101010101010101010101010101010101010101010
101010101010101010101010101010101010101010101010101010101010101010101010101010101010
101010101010101010101010101010101010101010101010101010101010101010101010101010101010
101010101010101010101010101010101010101010101010101010101010101010101010101010101010
101010101010101010101010101010101010101010101010101010101010101010101010101010101010
101010101010101010101010101010101010101010101010101010101010101010101010101010101010
101010101010101010101010101010101010101010101010101010101010101010101010101010101010
101010101010101010101010101010101010101010101010101010101010101010101010101010101010
101010101010101010101010101010101010101010101010101010101010101010101010101010101010
101010101010101010101010101010101010101010101010101010101010101010101010101010101010
101010101010101010101010101010101010101010101010101010101010101010101010101010101010
101010101010101010101010101010101010101010101010101010101010101010101010101010101010
101010101010101010101010101010101010101010101010101010101010101010101010101010101010
1010101010101010101010101010101010101010101010101010101010101010
Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 105
 7.4 Public Key
Cryptography

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 106
Symmetric Versus Asymmetric Key Algorithms
Asymmetric Key Algorithms
 Asymmetric algorithms are also called public-key algorithms.
 Public-key algorithms are asymmetric algorithms based on the
use of two different keys, instead of one.
• Private key - This key must be know only by its owner.
• Public key - This key is known to everyone (it is public).
 The key used for encryption is different from the key used for
decryption.
• However, the decryption key cannot, in any reasonable amount of
time, be calculated from the encryption key and vice versa.
 Public-key systems have a clear advantage over symmetric
algorithms.
• There is no need to agree on a common key for both the sender
and the receiver.

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Symmetric Versus Asymmetric Key Algorithms
Asymmetric Key Algorithms Cont.
 Either key can be used for encryption, but the complementary
matched key is required for decryption.
• If a public key encrypts data, the matching private key decrypts
data.
• If a private key encrypts data, the matching public key decrypts
data.
Asymmetric Key Characteristics

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Symmetric Versus Asymmetric Key Algorithms
Public Key (Encrypt) + Private Key (Decrypt) = Confidentiality

The confidentiality objective of asymmetric algorithms is achieved

when the encryption process is started with the public key.

Alice Acquires Public Key

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Symmetric Versus Asymmetric Key Algorithms
Public Key (Encrypt) + Private Key (Decrypt) = Confidentiality Cont.

Alice Encrypts Message Using Bob’s Public Key

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Symmetric Versus Asymmetric Key Algorithms
Public Key (Encrypt) + Private Key (Decrypt) = Confidentiality Cont.

Bob Decrypts the Message Using the Private Key

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Symmetric Versus Asymmetric Key Algorithms
Private Key + Public Key = Authentication
The authentication objective of asymmetric algorithms is achieved
when the encryption process is started with the private key.
Alice Encrypts Message Using Her Private Key

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Symmetric Versus Asymmetric Key Algorithms
Private Key + Public Key = Authentication Cont.

Bob Requests Alice’s Public Key

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Symmetric Versus Asymmetric Key Algorithms
Private Key + Public Key = Authentication Cont.
Bob Deciphers the Message Using the Public Key

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Symmetric Versus Asymmetric Key Algorithms
Asymmetric Algorithms
When sending a message that ensures message confidentiality,
authentication and integrity, the combination of two encryption
phases is necessary.
 Phase 1 - Confidentiality
 Phase 2 - Authentication and Integrity

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 Symmetric Versus Asymmetric Key Algorithms
Asymmetric Algorithms Cont.

Phase 1 - Confidentiality

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Symmetric Versus Asymmetric Key Algorithms
Asymmetric Algorithms Cont.
Phase 2 - Authentication and Integrity

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Symmetric Versus Asymmetric Key Algorithms
Asymmetric Algorithms Cont.
Phase 2 - Authentication and Integrity

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Symmetric Versus Asymmetric Key Algorithms
Asymmetric Algorithms Cont.
Phase 2 - Authentication and Integrity

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Symmetric Versus Asymmetric Key Algorithms
Asymmetric Algorithms Cont.
 Well-known asymmetric key algorithms:
• Diffie-Hellman
• Digital Signature Standard (DSS), which incorporates the Digital
Signature Algorithm (DSA)
• RSA encryption algorithms
• ElGamal
• Elliptical curve techniques

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 120
Symmetric Versus Asymmetric Key Algorithms
Asymmetric Algorithms
Key length
Algorithm Description
(in bits)
Public key algorithm invented in 1976 by Whitfield Diffie and Martin Hellman that allows two parties to
agree on a key that they can use to encrypt messages.
Diffie-Hellman 512, 1024, 2048
Security depends on the assumption that it is easy to raise a number to a certain power, but difficult to
compute which power was used given the number and the outcome.

Digital Signature Created by NIST and specifies DSA as the algorithm for digital signatures.
Standard and
512 - 1024 DSA is a public key algorithm based on the ElGamal signature scheme.
Digital Signature
Algorithm Signature creation speed is similar with RSA, but is 10 to 40 times as slow for verification.

Developed by Ron Rivest, Adi Shamir, and Leonard Adleman at MIT in 1977.
It is an algorithm for public-key cryptography based on the difficulty of factoring very large numbers.
RSA encryption It is the first algorithm known to be suitable for signing and encryption, and is one of the first great
512 to 2048
algorithms advances in public key cryptography.
Widely used in electronic commerce protocols, and is believed to be secure given sufficiently long keys
and the use of up-to-date implementations.
An asymmetric key encryption algorithm for public-key cryptography which is based on the Diffie-
Hellman key agreement.
EIGamal 512 - 1024 Developed in 1984 and used in GNU Privacy Guard software, PGP, and other cryptosystems.
A disadvantage is that the encrypted message becomes very big, about twice the size of the original
message, and for this reason, it is only used for small messages, such as secret keys.

Elliptic curve cryptography was invented by Neil Koblitz in 1987 and by Victor Miller in 1986.
Elliptical curve
160 Can be used to adapt many cryptographic algorithms, such as Diffie-Hellman or ElGamal.
techniques
The main advantage of elliptic curve cryptography is that the keys can be much smaller.
Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 121
Digital Signatures
Using Digital Signatures
 Authenticity of digitally signed data
• Digital signatures authenticate a source, proving that a certain party
has seen and signed the data in question.
 Integrity of digitally signed data
• Digital signatures guarantee that the data has not changed from the
time it was signed.
 Nonrepudiation of the transaction
• The recipient can take the data to a third party, and the third party
accepts the digital signature as a proof that this data exchange did
take place.
• The signing party cannot repudiate that it has signed the data.

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Digital Signatures
Digital Signature Process
There are six steps to the digital signature process, as shown in the figure (next
slide):
1. The sending device, the signer, creates a hash of the document.
2. The sending device encrypts the hash with the private key of the signer.
3. The encrypted hash, known as the signature, is appended to the document.
4. The receiving device, the verifier, accepts the document with the digital
signature and obtains the public key of the sending device.
5. The receiving device decrypts the signature using the public key of the
sending device. This step unveils the assumed hash value of the sending
device.
6. The receiving device makes a hash of the received document, without its
signature, and compares this hash to the decrypted signature hash. If the
hashes match, the document is authentic; it was signed by the assumed
signer and has not changed since it was signed.

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Digital Signatures
Digital Signature Process Cont.

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Digital Signatures
Digitally Signed Code
Digitally signing code provides several assurances about the code:
• The code has not been modified since it left the software publisher.
• The code is authentic and is actually sourced by the publisher.
• The publisher undeniably publishes the code.
• This provides nonrepudiation of the act of publishing.

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Digital Signatures
Digital Signature Algorithm
 Well-known asymmetric algorithms, such as RSA or Digital
Signature Algorithm (DSA), are typically used to perform digital
signing.
 In 1994, the U.S. NIST selected the DSA as the DSS. DSA is
based on the discrete logarithm problem and can only provide
digital signatures.
 A network administrator must decide whether RSA or DSA is
more appropriate for a given situation.
• DSA signature generation is faster than DSA signature verification.
• RSA signature verification is much faster than signature generation.

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Digital Signatures
Digital Signature Algorithm Cont.

DSA Scorecard

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Rivest, Shamir, and Alderman
RSA Asymmetric Algorithm
 RSA is one of the most common asymmetric algorithms.
 Ron Rivest, Adi Shamir, and Len Adleman invented the RSA
algorithm in 1977.
 Patented public-key algorithm.
• The patent expired in September 2000.
• The algorithm is now in the public domain.

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Rivest, Shamir, and Alderman
RSA Summary
 RSA is about 100 times slower than DES in hardware.
 RSA about 1,000 times slower than DES in software. This
performance problem is the main reason that RSA is typically
used only to protect small amounts of data.
 RSA is mainly used to ensure confidentiality of data by performing
encryption, and to perform authentication of data or
nonrepudiation of data, or both, by generating digital signatures.

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Public Key Infrastructure
Public Key Infrastructure Overview
 PKI is the service framework needed to support large-scale public
key-based technologies. Scalable solutions that are an extremely
important authentication solution for VPNs.
 PKI is a set of technical, organizational, and legal components
that are needed to establish a system that enables large-scale
use of public key cryptography to provide authenticity,
confidentiality, integrity, and nonrepudiation services.
 The PKI framework consists of the hardware, software, people,
policies, and procedures needed to create, manage, store,
distribute, and revoke digital certificates.

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Public Key Infrastructure
Public Key Infrastructure Overview

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Public Key Infrastructure
PKI Framework
 PKI Certificates are published public information containing the
binding between the names and public keys of entities.
 PKI Certificate Authority (CA)
• A trusted third-party entity that issues certificates.
• A CA always signs the certificate of a user.
• Every CA also has a certificate containing its public key, signed by
itself.
• This is called a CA certificate or, more properly, a self-signed CA
certificate.

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Public Key Infrastructure
Components of a PKI
 Building a large PKI involves a huge amount of organizational and
legal work.
 There are five main components of a PKI:
• PKI users, such as people, devices, and servers
• CAs for key management
• Storage and protocols
• Supporting organizational framework, known as practices and user
authentication using Local Registration Authorities (LRAs)
• Supporting legal framework

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Public Key Infrastructure
Components of a PKI Cont.
 The trust in the certificate is usually determined by how rigorous
the procedure was that verified the identity of the holder when the
certificate was issued:
• Class 0 – Used for testing purposes in which no checks have been
performed.
• Class 1 - Used for individuals with a focus on email.
• Class 2 - Used for organizations for which proof of identity is
required.
• Class 3 - Used for servers and software signing for which
independent verification and checking of identity and authority is
done by the issuing certificate authority.
• Class 4 - Used for online business transactions between
companies.
• Class 5 - Used for private organizations or governmental security.

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Public Key Infrastructure
PKI Usage Scenarios
 Some PKIs offer the possibility, or even require the use, of two
key pairs per entity.
• The first public and private key pair is intended only for encryption
operations. to back up only the private key of the encrypting pair.
• The signing private key remains with the user, enabling true
nonrepudiation.
• These keys are sometimes called usage or special keys.

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PKI Standards
Interoperability of Different PKI Vendors
 Interoperability between different PKI vendors is still an issue.
 To address this interoperability concern, the IETF formed the
Public-Key Infrastructure X.509 (PKIX) workgroup, that is
dedicated to promoting and standardizing PKI in the Internet.
 This workgroup has published a draft set of standards, X.509,
detailing common data formats and PKI-related protocols in a
network.
IETF PKIX Workgroup

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PKI Standards
X.509 Standard
 Defines basic PKI formats, such as the certificate and certificate
revocation list (CRL) format to enable basic interoperability.
 Widely used for years:
• Secure web servers: SSL and TLS
• Web browsers: SSL and TLS
• Email programs: S/MIME
• IPsec VPN: IKE

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PKI Standards
Public-Key Cryptography Standards
 The public-key cryptography standards (PKCS) refers to a group
of standards devised and published by RSA Laboratories.
• PKCS provides basic interoperability of applications that use public-
key cryptography.
• PKCS defines the low-level formats for the secure exchange of
arbitrary data, such as an encrypted piece of data or a signed piece
of data.

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PKI Standards
Public-Key Cryptography Standards Cont.
 PKCS #1: RSA Cryptography Standard
 PKCS #3: DH Key Agreement Standard
 PKCS #5: Password-Based Cryptography Standard
 PKCS #6: Extended-Certificate Syntax Standard
 PKCS #7: Cryptographic Message Syntax Standard
 PKCS #8: Private-Key Information Syntax Standard
 PKCS #10: Certification Request Syntax Standard
 PKCS #12: Personal Information Exchange Syntax Standard
 PKCS #13: Elliptic Curve Cryptography Standard
 PKCS #15: Cryptographic Token Information Format Standard

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 139
PKI Standards
Simple Certificate Enrollment Protocol
 The IETF designed the Simple
Certificate Enrollment Protocol
(SCEP) to make issuing and
revocation of digital certificates
as scalable as possible.
 The goal of SCEP is to support
the secure issuance of
certificates to network devices in
a scalable manner using existing
technology whenever possible.

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Certificate Authorities
Single-Root PKI Topology
 PKIs can form different topologies of trust, including:
• Single-root PKI topologies
• Hierarchical CA topologies
• Cross-certified CA topologies

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Certificate Authorities
Single-Root PKI Topology Cont.
 In the single-root PKI model, a single CA issues all the certificates
to the end users. The benefit is simplicity.
 There are also disadvantages:
• It is difficult to scale to a large environment.
• It needs a strictly centralized administration.
• It creates a single point of failure.

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Certificate Authorities
Hierarchical CA Topology
 More complex topologies involve
multiple CAs within the same
organization.
 The main benefits of a hierarchical
PKI topology are increased
scalability and manageability.
 Trust decisions can now be
hierarchically distributed to smaller
branches.

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Certificate Authorities
Hierarchical CA Topology Cont.
 Another approach to
hierarchical PKIs is called a
cross-certified CA or cross-
certifying.
 A multiple, flat, single-root CAs
establish trust relationships
horizontally by cross-certifying
their own CA certificates.

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Certificate Authorities
Complex PKI Topology
 Usually tasks offloaded to an RA
• Authentication of users when they enroll with the PKI
• Key generation for users that cannot generate their own keys
• Distribution of certificates after enrollment
 Additional tasks include
• Verifying user identity
• Establishing passwords for certificate management transactions
• Submitting enrollment requests to the CA
• Handling certificate revocation and re-enrollment

Presentation_ID © 2008 Cisco Systems, Inc. All rights reserved. Cisco Confidential 145
Certificate Authorities
Complex PKI Topology Cont.

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Digital Certificates and CAs
Step 1: Retrieve CA Certificates
 In the CA authentication procedure, the first step when contacting
the PKI is to securely obtain a copy of the public key of the CA.
 The public key verifies all the certificates issued by the CA and is
vital for the proper operation of the PKI.
 The public key, called the self-signed certificate, is also
distributed in the form of a certificate issued by the CA itself.
 Only a root CA issues self-signed certificates.

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Digital Certificates and CAs
Step 1: Retrieve CA Certificates Cont.

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Digital Certificates and Cas
Step 2: Submitting Certificate Requests to the CA

After retrieving the CA certificate, Alice and Bob submit certificate

requests to the CA.

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Digital Certificates and CAs
Step 3: Authenticate Endpoints
Having installed certificates signed by the same CA, Bob and Alice
are now ready to authenticate each other.

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Digital Certificates and CAs
PKA Summary
 PKI as an authentication mechanism has several characteristics:
• To authenticate each other, users must obtain the certificate of the
CA and their own certificate.
• Public-key systems use asymmetric keys in which one is public and
the other one is private.
• One of the features of these algorithms is that whatever is
encrypted using one key can only be decrypted using the other
key.
• This provides nonrepudiation.
• Key management is simplified, because two users can freely
exchange the certificates.
• The validity of the received certificates is verified using the
public key of the CA, which the users have in their possession.
• Because of the strength of the algorithms involved, administrators
can set a very long lifetime for the certificates, typically a lifetime
that is measured in years.
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Summary
 Secure communications employs cryptographic methods to
protect the integrity, authentication, and confidentiality of network
traffic when traversing the public Internet.
 Cryptology is the combination of:
• Cryptography - Related to the making and using of encryption
methods.
• Cryptanalysis - Related to the solving or breaking of a
cryptographic encryption method.
 Cryptographic hashes play a vital role when securing network traffic. For
example:
• Integrity is provided by using the MD5 algorithm or the SHA-1
algorithm.
• Authenticity is provided using HMAC.
• Confidentiality is provided using various encryption algorithms.

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Summary Cont.
 Encryption can be implemented using a:
• Symmetric algorithm - Various symmetric encryption algorithms
can be used, including DES, 3DES, AES, or SEAL.
• Each option varies with regard to the degree of protection and
the ease of implementation.
• DH is a hashing algorithm used to support DES, 3DES, and
AES.
• Asymmetric algorithm - These can use digital signatures, such as
the RSA algorithm, to provide authentication and confidentiality.
Asymmetric encryption is usually implemented using PKI.

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