CCNA Security

Chapter Seven
Cryptographic Systems

© 2009 Cisco Learning Institute. 1

Lesson Planning

• This lesson should take 3-4 hours to present

• The lesson should include lecture,
demonstrations, discussions and assessments
• The lesson can be taught in person or using
remote instruction

© 2009 Cisco Learning Institute. 2

Major Concepts

• Describe how the types of encryption, hashes, and digital signatures

work together to provide confidentiality, integrity, and authentication
• Describe the mechanisms to ensure data integrity and authentication
• Describe the mechanisms used to ensure data confidentiality
• Describe the mechanisms used to ensure data confidentiality and
authentication using a public key

© 2009 Cisco Learning Institute. 3

Lesson Objectives

Upon completion of this lesson, the successful participant will be

able to:
1. Describe the requirements of secure communications including
integrity, authentication, and confidentiality
2. Describe cryptography and provide an example
3. Describe cryptanalysis and provide an example
4. Describe the importance and functions of cryptographic hashes
5. Describe the features and functions of the MD5 algorithm and of the
SHA-1 algorithm
6. Explain how we can ensure authenticity using HMAC
7. Describe the components of key management

© 2009 Cisco Learning Institute. 4

Lesson Objectives

8. Describe how encryption algorithms provide confidentiality

9. Describe the function of the DES algorithms
10. Describe the function of the 3DES algorithm
11. Describe the function of the AES algorithm
12. Describe the function of the Software Encrypted Algorithm (SEAL) and
the Rivest ciphers (RC) algorithm
13. Describe the function of the DH algorithm and its supporting role to
DES, 3DES, and AES
14. Explain the differences and their intended applications
15. Explain the functionality of digital signatures
16. Describe the function of the RSA algorithm
17. Describe the principles behind a public key infrastructure (PKI)

© 2009 Cisco Learning Institute. 5

Lesson Objectives

18. Describe the various PKI standards

19. Describe the role of CAs and the digital certificates that they
issue in a PKI
20. Describe the characteristics of digital certificates and CAs

© 2009 Cisco Learning Institute. 6

Secure Communications
CSA

MARS

Firewall

VPN
IPS

CSA

VPN Iron Port CSA

Remote Branch CSA
CSA CSA

CSA
CSA

Web Email
Server Server DNS

• Traffic between sites must be secure

• Measures must be taken to ensure it cannot be altered, forged, or deciphered if intercepted

© 2009 Cisco Learning Institute. 7

Authentication

• An ATM Personal
Information Number (PIN)
is required for
authentication.
• The PIN is a shared
secret between a bank
account holder and the
financial institution.

© 2009 Cisco Learning Institute. 8

Integrity

• An unbroken wax seal on an envelop ensures integrity.

• The unique unbroken seal ensures no one has read the
contents.

© 2009 Cisco Learning Institute. 9

Confidentiality

• Julius Caesar
would send
encrypted
messages to his
I O D Q N H D V W generals in the
battlefield.
D W W D F N D W G D Z Q • Even if
intercepted, his
enemies usually
could not read, let
alone decipher,
the messages.

© 2009 Cisco Learning Institute. 10

History

Scytale - (700 BC)

Vigenère table

German Enigma Machine

Jefferson encryption device

© 2009 Cisco Learning Institute. 11

Transposition Ciphers

1
FLANK EAST The clear text message would be
ATTACK AT DAWN encoded using a key of 3.
Clear Text

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

3
FKTTAW The clear text message would
LNESATAKTAN
AATCD appear as follows.
Ciphered Text

© 2009 Cisco Learning Institute. 12

Substitution Ciphers
Caesar Cipher

1
FLANK EAST The clear text message would be
ATTACK AT DAWN encoded using a key of 3.
Clear text

Shift the top

2 scroll over by
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 three characters
(key of 3), an 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 A B C
becomes D, B
becomes E, and
so on.

3
IODQN HDVW The clear text message would
DWWDFN DW GDZQ be encrypted as follows using a
key of 3.
Cipherered text

© 2009 Cisco Learning Institute. 13

Cipher Wheel

1
FLANK EAST The clear text message would be
ATTACK AT DAWN encoded using a key of 3.
Clear text

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

3
IODQN HDVW The clear text message would
DWWDFN DW GDZQ appear as follows using a key of 3.
Cipherered text

© 2009 Cisco Learning Institute. 14

Vigenѐre Table
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

© 2009 Cisco Learning Institute. 15

Stream Ciphers

• Invented by the Norwegian Army Signal

Corps in 1950, the ETCRRM machine
uses the Vernam stream cipher method.
• It was used by the US and Russian
governments to exchange information.
• Plain text message is eXclusively OR'ed
with a key tape containing a random
stream of data of the same length to
generate the ciphertext.
• Once a message was enciphered the
key tape was destroyed.
• At the receiving end, the process was
reversed using an identical key tape to
decode the message.

© 2009 Cisco Learning Institute. 16

Defining Cryptanalysis

Allies decipher secret

NAZI encryption code!

Cryptanalysis is from the Greek words kryptós (hidden), and analýein (to loosen or to
untie). It is the practice and the study of determining the meaning of encrypted
information (cracking the code), without access to the shared secret key.

© 2009 Cisco Learning Institute. 17

Cryptanalysis Methods

Brute Force Attack

Known Ciphertext

Successfully
Unencrypted
Key found

With a Brute Force attack, the attacker has some portion of

ciphertext. The attacker attempts to unencrypt the ciphertext with
all possible keys.
© 2009 Cisco Learning Institute. 18
Meet-in-the-Middle Attack

Known Ciphertext Known Plaintext

Use every possible
decryption key until a result
is found matching the
corresponding plaintext.
Use every possible
encryption key until a
result is found matching
the corresponding
ciphertext.

MATCH of
Ciphertext!
Key found

With a Meet-in-the-Middle attack, the attacker has some portion of

text in both plaintext and ciphertext. The attacker attempts to
unencrypt the ciphertext with all possible keys while at the same time
encrypt the plaintext with another set of possible keys until one match
is found.
© 2009 Cisco Learning Institute. 19
Choosing a Cryptanalysis Method

The graph outlines the

1
frequency of letters in the
English language.
For example, the letters E,
T and A are the most
popular.

There are 6 occurrences of the cipher

letter D and 4 occurrences of the cipher
letter W.
2 Replace the cipher letter D first with
IODQN HDVW
DWWDFN DW GDZQ popular clear text letters including E, T,
and finally A.
Cipherered text
Trying A would reveal the shift pattern of 3.
© 2009 Cisco Learning Institute. 20
Defining Cryptology

Cryptology

Cryptography Cryptanalysis

© 2009 Cisco Learning Institute. 21

Cryptanalysis

© 2009 Cisco Learning Institute. 22

Cryptographic Hashes, Protocols,
and Algorithm Examples

Integrity Authentication Confidentiality

MD5 HMAC-MD5 DES

SHA HMAC-SHA-1 3DES
RSA and DSA AES
SEAL
RC (RC2, RC4, RC5, and RC6)

HASH HASH w/Key

NIST Rivest Encryption

© 2009 Cisco Learning Institute. 23

Hashing Basics

• Hashes are used for

integrity assurance. Data of Arbitrary
Length
• Hashes are based on
one-way functions.
• The hash function hashes
arbitrary data into a fixed-
length digest known as
the hash value, message
digest, digest, or
fingerprint.
Fixed-Length
Hash Value
e883aa0b24c09f

© 2009 Cisco Learning Institute. 24

Hashing Properties

Arbitrary X
length text Why is x not in
Parens?

h = H (x)

Hash
Function
(H)
Why is H in
Parens?

Hash h e883aa0b24c09f
Value

© 2009 Cisco Learning Institute. 25

Hashing in Action

•Vulnerabl
e to man-in-the-middle attacks
- Hashing does not provide security to transmission.
•Well-
known hash functions I would like to
- MD5 with 128-bit hashes cash this
- SHA-1 with 160-bit hashes check.

Internet
Pay to Terry Smith Pay to Alex Jones
$100.00 $1000.00
One Hundred and xx/100 One Thousand and xx/100
Dollars Dollars
4ehIDx67NMop9 12ehqPx67NMoX

Match = No changes
No match = Alterations
© 2009 Cisco Learning Institute. 26
MD5

• MD5 is a ubiquitous hashing

algorithm
• Hashing properties
- One-way function—easy to
compute hash and infeasible to MD5
compute data given a hash
- Complex sequence of simple
binary operations (XORs,
rotations, etc.) which finally
produces a 128-bit hash.

© 2009 Cisco Learning Institute. 27

SHA

• SHA is similar in design to the MD4 and MD5

family of hash functions
- Takes an input message of no more than 264 bits
- Produces a 160-bit message digest

• The algorithm is slightly slower than MD5. SHA

• SHA-1 is a revision that corrected an unpublished
flaw in the original SHA.
• SHA-224, SHA-256, SHA-384, and SHA-512 are
newer and more secure versions of SHA and are
collectively known as SHA-2.

© 2009 Cisco Learning Institute. 28

Hashing Example

In this example the clear text entered is displaying hashed

results using MD5, SHA-1, and SHA256. Notice the
difference in key lengths between the various algorithm. The
longer the key, the more secure the hash function.

© 2009 Cisco Learning Institute. 29

Features of HMAC

• Uses an additional secret

key as input to the hash Data of Arbitrary Secret
function Length + Key

• The secret key is known to

the sender and receiver
- Adds authentication to
integrity assurance
- Defeats man-in-the-middle
attacks Fixed Length
Authenticated e883aa0b24c09f
Hash Value
• Based on existing hash
functions, such as MD5 The same procedure is used for
and SHA-1. generation and verification of
secure fingerprints
© 2009 Cisco Learning Institute. 30
HMAC Example

Data Received Data Secret Key

Pay to Terry Smith $100.00 Secret
Pay to Terry Smith $100.00
One Hundred and xx/100 Dollars Key One Hundred and xx/100 Dollars

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.
© 2009 Cisco Learning Institute. 31
Using Hashing

Data Integrity Data Authenticity

e883aa0b24c09f
Fixed-Length Hash
Value

Entity Authentication

• Routers use hashing with secret keys

• Ipsec gateways and clients use hashing algorithms
• Software images downloaded from the website have checksums
• Sessions can be encrypted

© 2009 Cisco Learning Institute. 32

Key Management

Key Generation Key Verification

Key
Management Key Storage
Key Exchange

Key Revocation and Destruction

© 2009 Cisco Learning Institute. 33

Keyspace
DES Key Keyspace # of Possible Keys
56-bit 256 72,000,000,000,000,000
111111111111111111111111

11111111111111111111111111111111

Twice as
57-bit 257 144,000,000,000,000,000 much time
111111111111111111111111

11111111111111111111111111111111 1 Four time as

much time

58-bit 258 288,000,000,000,000,000

111111111111111111111111

11111111111111111111111111111111 11 With 60-bit DES

an attacker would
require sixteen
59-bit 259 576,000,000,000,000,000 more time than
111111111111111111111111 56-bit DES
11111111111111111111111111111111 111

60-bit 260 1,152,000,000,000,000,000

111111111111111111111111
For each bit added to the DES key, the attacker would require twice the amount of time to
11111111111111111111111111111111 1111
search the keyspace.
Longer keys are more secure but are also more resource intensive and can affect throughput.

© 2009 Cisco Learning Institute. 34

Types of Keys
Symmetric Asymmetric Digital
Hash
Key Key Signature

Protection up
to 3 years 80 1248 160 160
Protection up
to 10 years 96 1776 192 192
Protection up
to 20 years 112 2432 224 224
Protection up
to 30 years 128 3248 256 256
Protection against
quantum computers 256 15424 512 512

 Calculations are based on the fact that computing power will continue to
grow at its present rate and the ability to perform brute-force attacks will
grow at the same rate.
 Note the comparatively short symmetric key lengths illustrating that
symmetric algorithms are the strongest type of algorithm.
© 2009 Cisco Learning Institute. 35
Key Properties

Shorter keys = faster

processing, but less secure

Longer keys = slower

processing, but more
secure

© 2009 Cisco Learning Institute. 36

Confidentiality and the OSI Model

• For Data Link Layer confidentiality, use proprietary link-

encrypting devices
• For Network Layer confidentiality, use secure Network Layer
protocols such as the IPsec protocol suite
• For Session Layer confidentiality, use protocols such as
Secure Sockets Layer (SSL) or Transport Layer Security (TLS)
• For Application Layer confidentiality, use secure e-mail, secure
database sessions (Oracle SQL*net), and secure messaging
(Lotus Notes sessions)

© 2009 Cisco Learning Institute. 37

Symmetric Encryption

Pre-shared
Key key Key

Encrypt Decrypt
$1000 $!@#IQ $1000

• Best known as shared-secret key algorithms

• The usual key length is 80 - 256 bits
• A sender and receiver must share a secret key
• Faster processing because they use simple mathematical operations.
• Examples include DES, 3DES, AES, IDEA, RC2/4/5/6, and Blowfish.

© 2009 Cisco Learning Institute. 38

Symmetric Encryption and XOR

The XOR operator results in a 1 when the value of either

the first bit or the second bit is a 1

The XOR operator results in a 0 when neither or both of

the bits is 1

Plain Text 1 1 0 1 0 0 1 1
Key (Apply) 0 1 0 1 0 1 0 1
XOR (Cipher 1 0 0 0 0 1 1 0
Text)
Key (Re-Apply) 0 1 0 1 0 1 0 1
XOR (Plain Text) 1 1 0 1 0 0 1 1

© 2009 Cisco Learning Institute. 39

Asymmetric Encryption
Two separate
keys which are
Encryption Key not shared Decryption Key

Encrypt Decrypt
$1000 %3f7&4 $1000

• Also known as public key algorithms

• The usual key length is 512–4096 bits
• A sender and receiver do not share a secret key
• Relatively slow because they are based on difficult computational
algorithms
• Examples include RSA, ElGamal, elliptic curves, and DH.

© 2009 Cisco Learning Institute. 40

Asymmetric Example : Diffie-Hellman
Get Out Your Calculators?

© 2009 Cisco Learning Institute. 41

Symmetric Algorithms

Symmetric Key length Description

Encryption (in bits)
Algorithm
DES 56 Designed at IBM during the 1970s and was the NIST standard until 1997.
Although considered outdated, DES remains widely in use.
Designed to be implemented only in hardware, and is therefore extremely slow
in software.

3DES 112 and 168 Based on using DES three times which means that the input data is encrypted
three times and therefore considered much stronger than DES.
However, it is rather slow compared to some new block ciphers such as AES.

AES
Software Encryption
Algorithm (SEAL)
The RC series
© 2009 Cisco Learning Institute.
128, 192, and 256 Fast in both software and hardware, is relatively easy to implement, and
requires little memory.
As a new encryption standard, it is currently being deployed on a large scale.
160 SEAL is an alternative algorithm to DES, 3DES, and AES.
It uses a 160-bit encryption key and has a lower impact to the CPU when
compared to other software-based algorithms.
RC2 (40 and 64) A set of symmetric-key encryption algorithms invented by Ron Rivest.
RC4 (1 to 256) RC1 was never published and RC3 was broken before ever being used.
RC5 (0 to 2040) RC4 is the world's most widely used stream cipher.
RC6 (128, 192, and RC6, a 128-bit block cipher based heavily on RC5, was an AES finalist
256)
developed in 1997.
42
Symmetric Encryption Techniques

Enc
Mes rypted
blank blank 1100101 01010010110010101 sag
e
01010010110010101

64 bits 64bits 64bits

Block Cipher – encryption is completed

in 64 bit blocks

Enc
Mes rypted
sag
e

0101010010101010100001001001001 0101010010101010100001001001001

Stream Cipher – encryption is one bit

at a time

© 2009 Cisco Learning Institute. 43

Selecting an Algorithm

DES 3DES AES

The algorithm is trusted by Been Yes Verdict is still

the cryptographic community replaced by out
3DES
The algorithm adequately No Yes Yes
protects against brute-force
attacks

© 2009 Cisco Learning Institute. 44

DES Scorecard

Description Data Encryption Standard

Timeline Standardized 1976

Type of Algorithm Symmetric

Key size (in bits) 56 bits

Speed Medium

Time to crack Days (6.4 days by the COPACABANA machine, a specialized

(Assuming a computer could try 255 cracking device)
keys per second)

Resource Consumption Medium

© 2009 Cisco Learning Institute. 45

Block Cipher Modes

ECB CBC
Message of Five 64-Bit Blocks Message of Five 64-Bit Blocks

Initialization
Vector
DES

DES
DES

DES

DES

DES

DES

DES

DES

DES
© 2009 Cisco Learning Institute. 46
Considerations

• Change keys frequently to help

prevent brute-force attacks. DES

• Use a secure channel to

communicate the DES key from
the sender to the receiver.
• Consider using DES in CBC
mode. With CBC, the
encryption of each 64-bit block
depends on previous blocks.
• Test a key to see if it is a weak
key before using it.

© 2009 Cisco Learning Institute. 47

3DES Scorecard

Description Triple Data Encryption Standard

Timeline Standardized 1977

Type of Algorithm Symmetric

Key size (in bits) 112 and 168 bits

Speed Low

Time to crack 4.6 Billion years with current technology

(Assuming a computer could try 255
keys per second)

Resource Consumption Medium

© 2009 Cisco Learning Institute. 48

Encryption Steps

The clear text from Alice is

encrypted using Key 1. That
ciphertext is decrypted
using a different key, Key 2.
1 Finally that ciphertext is
encrypted using another
key, Key 3.

When the 3DES ciphered text

2 is received, the process is
reversed. That is, the
ciphered text must first be
decrypted using Key 3,
encrypted using Key 2, and
finally decrypted using Key 1.

© 2009 Cisco Learning Institute. 49

AES Scorecard

Description Advanced Encryption Standard

Timeline Official Standard since 2001

Type of Algorithm Symmetric

Key size (in bits) 128, 192, and 256

Speed High

Time to crack 149 Trillion years

(Assuming a computer could try 255
keys per second)

Resource Consumption Low

© 2009 Cisco Learning Institute. 50

Advantages of AES

• The key is much stronger due to the key length

• AES runs faster than 3DES on comparable hardware
• AES is more efficient than DES and 3DES on
comparable hardware
The plain text is now
encrypted using 128
AES

An attempt at
deciphering the text
using a lowercase,
and incorrect key

© 2009 Cisco Learning Institute. 51

SEAL Scorecard
Description Software-Optimized Encryption Algorithm

Timeline First published in 1994. Current version is 3.0 (1997)

Type of Algorithm Symmetric

Key size (in bits) 160

Speed High

Time to crack Unknown but considered very safe

(Assuming a computer could try 255
keys per second)

Resource Consumption Low

© 2009 Cisco Learning Institute. 52

Rivest Codes Scorecard

Description RC2 RC4 RC5 RC6

Timeline 1987 1987 1994 1998

Type of Algorithm Block cipher Stream Block cipher Block cipher

cipher
Key size (in bits) 40 and 64 1 - 256 0 to 2040 bits 128, 192, or
(128 256
suggested)

© 2009 Cisco Learning Institute. 53

DH Scorecard
Description Diffie-Hellman Algorithm

Timeline 1976

Type of Algorithm Asymmetric

Key size (in bits) 512, 1024, 2048

Speed Slow

Time to crack Unknown but considered very safe

(Assuming a computer could try
255 keys per second)

Resource Medium
Consumption

© 2009 Cisco Learning Institute. 54

Using Diffie-Hellman
Alice Bob
Shared Secret Calc Shared Secret Calc

1 5, 23 1 5, 23
3
2 6 56mod 23 = 8 8

1. Alice and Bob agree to use the same two numbers. For example, the base number g= 5
and prime number p= 23
2. Alice now chooses a secret number x= 6.
3. Alice performs the DH algorithm: gx modulo p = ( 56 modulo 23) = 8 (Y) and
sends the new number 8 (Y) to Bob.
© 2009 Cisco Learning Institute. 55
Using Diffie-Hellman

Alice Bob
Shared Secret Calc Shared Secret Calc

5, 23 5, 23
6 56mod 23 = 8 8 15 4

19 515 mod 23 = 19

19 mod 23 = 2 2
5
6
6 815 mod 23 =

15, performed the DH algorithm:

4. Meanwhile Bob has also chosen a secret number x=

g modulo p = (515 modulo 23)

x 23 = 19 (Y) and sent the new number 19 (Y) to
Alice. The result (22) is the same
for both Alice and Bob.
196 modulo 23) = 2.
5. Alice now computes Yx modulo p = (
This number can now be
used as a shared secret
key by the encryption
6. Bob now computes Y modulo p = (86 modulo 23) = 2.
x algorithm.

© 2009 Cisco Learning Institute. 56

Asymmetric Key Characteristics

Encryption Decryption
Key Key
Plain Encryption Encrypted Decryption Plain
text text text

• Key length ranges from 512–4096 bits

• Key lengths greater than or equal to 1024 bits can be trusted
• Key lengths that are shorter than 1024 bits are considered
unreliable for most algorithms

© 2009 Cisco Learning Institute. 57

Public Key (Encrypt) + Private Key
(Decrypt) = Confidentiality

Computer A acquires
Computer B’s public key
Can I get your Public Key please? Bob’s Public
1 Key
Here is my Public Key.

Bob’s Public
Computer A transmits Bob’s Private
2 4
Key The encrypted message Key

Computer
Computer to Computer B Encrypted
Text B
A
Encryption Encryption
Algorithm Algorithm

Encrypted 3 Computer B uses

Text its private key to
decrypt and reveal
Computer A uses Computer B’s
the message
public key to encrypt a message
using an agreed-upon algorithm

© 2009 Cisco Learning Institute. 58

Private Key (Encrypt) + Public Key
(Decrypt) = Authentication
Bob uses the public key to
Alice encrypts a message successfully decrypt the message
with her private key and authenticate that the message
did, indeed, come from Alice.
Alice’s Private
1 Key
Encrypted
Text

Encryption
Alice transmits the 4
Alice’s Public
Key

Algorithm encrypted message Encrypted

2 to Bob Text

Encrypted
Computer Text
3 Computer Encryption

A B
Algorithm

Alice’s Public Can I get your Public Key please?

Key
Here is my Public Key

Bob needs to verify that the message

actually came from Alice. He requests
and acquires Alice’s public key

© 2009 Cisco Learning Institute. 59

Asymmetric Key Algorithms
Key length Description
(in bits)

DH 512, 1024, Invented in 1976 by Whitfield Diffie and Martin Hellman.

2048 Two parties to agree on a key that they can use to encrypt messages
The assumption is 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 512 - 1024 Created by NIST and specifies DSA as the algorithm for digital signatures.
Standard (DSS) and A public key algorithm based on the ElGamal signature scheme.
Digital Signature
Algorithm (DSA) Signature creation speed is similar with RSA, but is slower for verification.

RSA encryption 512 to 2048 Developed by Ron Rivest, Adi Shamir, and Leonard Adleman at MIT in 1977
algorithms Based on the current difficulty of factoring very large numbers
Suitable for signing as well as encryption
Widely used in electronic commerce protocols

EIGamal 512 - 1024 Based on the Diffie-Hellman key agreement.

Described by Taher Elgamal in 1984and is used in GNU Privacy Guard software,
PGP, and other cryptosystems.
The encrypted message becomes about twice the size of the original message and
for this reason it is only used for small messages such as secret keys

Elliptical curve 160 Invented by Neil Koblitz in 1987 and by Victor Miller in 1986.
techniques Can be used to adapt many cryptographic algorithms
Keys can be much smaller

© 2009 Cisco Learning Institute. 60

Security Services- Digital Signatures

• Authenticates a source,
proving a certain party
has seen, and has signed,
the data in question
• Signing party cannot
repudiate that it signed
the data
• Guarantees that the data
has not changed from the
time it was signed Authenticity
Integrity
Nonrepudiation

© 2009 Cisco Learning Institute. 61

Digital Signatures

• The signature is authentic and

not forgeable: The signature is
proof that the signer, and no one
else, signed the document.
• The signature is not reusable:
The signature is a part of the document and cannot be moved to a
different document.
• The signature is unalterable: After a document is signed, it cannot be
altered.
• The signature cannot be repudiated: For legal purposes, the signature
and the document are considered to be physical things. The signer cannot
claim later that they did not sign it.

© 2009 Cisco Learning Institute. 62

 The Digital Signature Process

The sending device creates

a hash of the document
The receiving device Validity of the digital
Data accepts the document signature is verified
Confirm with digital signature
and obtains the public key Signature Verified
Order
0a77b3440…

1 hash Signed Data 6

Signature Confirm
Key Order 4
____________
Encrypted 0a77b3440…
hash Signature is
2 Signature
Algorithm verified with
The sending device 3 the verification
encrypts only the hash key
0a77b3440…
with the private key
of the signer The signature algorithm Verification
5

generates a digital signature Key

and obtains the public key
© 2009 Cisco Learning Institute. 63
Code Signing with Digital Signatures

• The publisher of the software attaches a digital signature to the

executable, signed with the signature key of the publisher.
• The user of the software needs to obtain the public key of the
publisher or the CA certificate of the publisher if PKI is used.

© 2009 Cisco Learning Institute. 64

DSA Scorecard

Description Digital Signature Algorithm (DSA)

Timeline 1994

Type of Algorithm Provides digital signatures

Advantages: Signature generation is fast

Disadvantages: Signature verification is slow

© 2009 Cisco Learning Institute. 65

RSA Scorecard

Description Ron Rivest, Adi Shamir, and Len Adleman

Timeline 1977

Type of Algorithm Asymmetric algorithm

Key size (in bits) 512 - 2048

Advantages: Signature verification is fast

Disadvantages: Signature generation is slow

© 2009 Cisco Learning Institute. 66

Properties of RSA

• One hundred times slower than

DES in hardware
• One thousand times slower
than DES in software
• Used to protect small amounts
of data
• Ensures confidentiality of data
thru encryption
• Generates digital signatures for
authentication and
nonrepudiation of data

© 2009 Cisco Learning Institute. 67

Public Key Infrastructure

Alice applies for a driver’s license.

She receives her driver’s license

after her identity is proven.

Alice attempts to cash a check.

Her identity is accepted after her

driver’s license is checked.

© 2009 Cisco Learning Institute. 68

Public Key Infrastructure

PKI terminology to remember:

PKI:
A service framework (hardware, software, people, policies
and procedures) needed to support large-scale public key-
based technologies.
Certificate:
A document, which binds together the name of the entity
and its public key and has been signed by the CA
Certificate authority (CA):
The trusted third party that signs the public keys of
entities in a PKI-based system

© 2009 Cisco Learning Institute. 69

 CA Vendors and Sample Certificates

http://www.verisign.com http://www.entrust.com

http://www.verizonbusiness.com/

http://www.novell.com

http://www.rsa.com/
http://www.microsoft.com

© 2009 Cisco Learning Institute. 70

Usage Keys

• When an encryption certificate is used much more frequently than a

signing certificate, the public and private key pair is more exposed due
to its frequent usage. In this case, it might be a good idea to shorten
the lifetime of the key pair and change it more often, while having a
separate signing private and public key pair with a longer lifetime.
• When different levels of encryption and digital signing are required
because of legal, export, or performance issues, usage keys allow an
administrator to assign different key lengths to the two pairs.
• When key recovery is desired, such as when a copy of a user’s private
key is kept in a central repository for various backup reasons, usage
keys allow the user to back up only the private key of the encrypting
pair. The signing private key remains with the user, enabling true
nonrepudiation.

© 2009 Cisco Learning Institute. 71

The Current State

X.509

• Many vendors have proposed and implemented

proprietary solutions
• Progression towards publishing a common set of
standards for PKI protocols and data formats

© 2009 Cisco Learning Institute. 72

X.509v3

• X.509v3 is a standard that

describes the certificate
structure.
• X.509v3 is used with:
- Secure web servers: SSL
and TLS
- Web browsers: SSL and
TLS
- Email programs: S/MIME
- IPsec VPNs: IKE

© 2009 Cisco Learning Institute. 73

X.509v3 Applications
SSL S/MIME
Internet
Mail
External Server
Web Server EAP-TLS

Cisco
Secure
Internet Enterprise ACS
Network
CA
Server

VPN
IPsec Concentrator

• Certificates can be used for various purposes.

• One CA server can be used for all types of authentication
as long as they support the same PKI procedures.

© 2009 Cisco Learning Institute. 74

RSA PKCS Standards

• 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

© 2009 Cisco Learning Institute. 75

Public Key Technology
PKCS#7
PKCS#10

CA
Certificate

Signed
Certificate

PKCS#7

• A PKI communication protocol used for VPN PKI enrollment

• Uses the PKCS #7 and PKCS #10 standards

© 2009 Cisco Learning Institute. 76

Single-Root PKI Topology

• Certificates issued by one CA

• Centralized trust decisions
• Single point of failure
Root CA

© 2009 Cisco Learning Institute. 77

Hierarchical CA Topology

Root CA

Subordinate
CA

• Delegation and distribution of trust

• Certification paths

© 2009 Cisco Learning Institute. 78

Cross-Certified CAs

CA2
CA1

CA3

• Mutual cross-signing of CA certificates

© 2009 Cisco Learning Institute. 79

Registration Authorities

After the Registration

Authority adds specific
information to the
2 CA certificate request and
Completed Enrollment
Request Forwarded to
the request is approved
CA under the organization’s
policy, it is forwarded
Hosts will submit on to the Certification
certificate requests RA Authority
to the RA 3
1
Certificate Issued
Enrollment
request

The CA will sign the certificate

request and send it back to
the host

© 2009 Cisco Learning Institute. 80

Retrieving the CA Certificates
Alice and Bob telephone the CA
administrator and verify the public key
and serial number of the certificate
Out-of-Band
Out-of-Band Authentication of
Authentication of the CA Certificate
the CA Certificate CA
Admin POTS
3
POTS 3

CA
1 CA
1
Certificate
CA
Certificate

Enterprise Network
2
2

Alice and Bob request the CA certificate Each system verifies the
that contains the CA public key validity of the certificate
© 2009 Cisco Learning Institute. 81
Submitting Certificate Requests
The CA administrator telephones to
The certificate is confirm their submittal and the public
retrieved and the key and issues the certificate by
certificate is installed 2 adding some additional data to the
onto the system request, and digitally signing it all
Out-of-Band Out-of-Band
Authentication of Authentication of
the CA Certificate CA the CA Certificate
Admin
POTS POTS

CA
1 Certificate
3 1 Certificate Request 3
Request

Enterprise Network

Both systems forward a certificate request which

includes their public key. All of this information is
encrypted using the public key of the CA
© 2009 Cisco Learning Institute. 82
Authenticating
Bob and Alice exchange certificates. The CA is no longer involved
2 2

Private Key (Alice) Private Key (Bob)

Certificate (Alice)

Certificate (Alice) Certificate (Bob)

Certificate (Bob)
CA Certificate CA Certificate

Each party verifies the digital signature on the certificate by hashing the
plaintext portion of the certificate, decrypting the digital signature using the
CA public key, and comparing the results.

© 2009 Cisco Learning Institute. 83

PKI Authentication Characteristics

• To authenticate each other, users have to obtain

the certificate of the CA and their own certificate.
These steps require the out-of-band verification of
the processes.
• Public-key systems use asymmetric keys where
one is public and the other one is private.
• 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,
administrators can set a very long lifetime for the
certificates.

© 2009 Cisco Learning Institute. 84

© 2009 Cisco Learning Institute. 85