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Cryptography

Chapter 3

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  • Explain the concept of cryptography.
  • Describe symmetric key encryption and the importance of key length.
  • Explain negotiation stage.
  • Explain initial authentication, including MS-CHAP.
  • Describe keying, including public key encryption.
  • Explain how electronic signatures, including digital signatures, digital certificates, and key-hashed message authentication codes (HMACs) work.
  • Describe public key encryption for authentication.
  • Describe quantum security.
  • Explain cryptographic systems including VPNs, SSL, and IPsec.

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  • Chapter 1 introduced the threat environment
  • Chapter 2 introduced the plan-protect-respond cycle and covered the planning phase
  • Chapters 3 through 9 will cover the protection phase
  • Chapter 3 introduces cryptography, which is important in itself and which is used in many other protections

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3.1 What Is Cryptography

3.2 Symmetric Key Encryption Ciphers

3.3 Cryptographic System Standards

3.4 The Negotiation Stage

3.5 Initial Authentication Stage

3.6 The Keying Stage

3.7 Message-by-Message Authentication

3.8 Quantum Security

3.9 Cryptographic Systems

3.10 SSL/TLS and IPsec

  • Cryptography is the use of mathematical operations to protect messages traveling between parties or stored on a computer
  • Confidentiality means that someone intercepting your communications cannot read them

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  • Confidentiality is only one cryptographic protection
  • Authentication means proving one’s identity to another so they can trust you more
  • Integrity means that the message cannot be changed or, if it is changed, that this change will be detected
  • Known as the CIA of cryptography

No, not that CIA

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  • Encryption for confidentiality needs a cipher (mathematical method) to encrypt and decrypt

The cipher cannot be kept secret

  • The two parties using the cipher also need to know a secret key or keys

A key is merely a long stream of bits (1s and 0s)

The key or keys must be kept secret

  • Cryptanalysts attempt to crack (find) the key

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n o p q r

+4

This is a very weak cipher.

Real ciphers use complex math.

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Figure 3-2

Plaintext Key Ciphertext
n 4 r
o 8 w
w 15 l
i 16
s 23
t 16
h 3
e 9
t 12
i 20
m 6
e 25

  • Substitution Ciphers

Substitute one letter (or bit) for another in each place

The cipher we saw in Figure 3-2 is a substitution cipher

  • Transposition Ciphers

Transposition ciphers do not change individual letters or bits, but they change their order

  • Most real ciphers use both substitution and transposition

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Key (Part 1)
Key (Part 2) 1 3 2
2 n o w
3 i s t
1 h e t
Key = 132 231

  • Ciphers can encrypt any message expressed in binary (1s and 0s)

This flexibility and the speed of computing makes this ciphers dominant for encryption today

  • Codes are more specialized

They substitute one thing for another

Usually a word for another word or a number for a word

Codes are good for humans and may be included in messages sent via encipherment

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Transmitted:

174346371783971…

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Message Code
From 17434
Akagi 63717
To 83971
Truk 11131
STOP 34058
ETA 53764
6 PM 73104
STOP 26733
Require 29798
B 72135
N 54678
STOP 61552

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Each extra bit

doubles the number of keys

Shaded keys are

Strong symmetric keys (>=100 bits)

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Key Length in Bits Number of Possible Keys
1 2
2 4
4 16
8 256
16 65,536
40 1,099,511,627,776
56 72,057,594,037,927,900
112 5,192,296,858,534,830,000,000,000,000,000,000
112 5.1923E+33
168 3.74144E+50
256 1.15792E+77
512 1.3408E+154

  • Note:

Public key/private key pairs (discussed later in the chapter) must be much longer than symmetric keys to be considered to be strong because of the disastrous consequences that could occur if a private key is cracked and because private keys cannot be changed frequently. Public keys and private keys must be at least 512 to 1,024 bits long

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3.1 What Is Cryptography

3.2 Symmetric Key Encryption Ciphers

3.3 Cryptographic System Standards

3.4 The Negotiation Stage

3.5 Initial Authentication Stage

3.6 The Keying Stage

3.7 Message-by-Message Authentication

3.8 Quantum Security

3.9 Cryptographic Systems

3.10 SSL/TLS and IPsec

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RC4 DES 3DES AES
Key Length (bits) 40 bits or more 56 112 or 168 128, 192, or 256
Key Strength Very weak at 40 bits Weak Strong Strong
Processing Requirements Low Moderate High Low
RAM Requirements Low Moderate Moderate Low
Remarks Can use keys of variable lengths Created in the 1970s Applies DES three times with two or three different DES keys Today’s gold standard for symmetric key encryption

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The DES cipher encrypts messages 64 bits at a time

The DES cipher (in codebook mode) needs two inputs

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3.1 What Is Cryptography

3.2 Symmetric Key Encryption Ciphers

3.3 Cryptographic System Standards

3.4 The Negotiation Stage

3.5 Initial Authentication Stage

3.6 The Keying Stage

3.7 Message-by-Message Authentication

3.8 Quantum Security

3.9 Cryptographic Systems

3.10 SSL/TLS and IPsec

  • Cryptographic Systems

Encryption for confidentiality is only one cryptographic protection

Individual users and corporations cannot be expected to master these many aspects of cryptography

Consequently, crypto protections are organized into complete cryptographic systems that provide a broad set of cryptographic protection

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  • Cryptographic Systems

Two parties first agree upon a particular cryptographic system to use

Each cryptographic system dialogue begins with three brief handshaking stages

The two parties then engage in cryptographically protected communication

This ongoing communication stage usually constitutes nearly all of the dialogue

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3.1 What Is Cryptography

3.2 Symmetric Key Encryption Ciphers

3.3 Cryptographic System Standards

3.4 The Negotiation Stage

3.5 Initial Authentication Stage

3.6 The Keying Stage

3.7 Message-by-Message Authentication

3.8 Quantum Security

3.9 Cryptographic Systems

3.10 SSL/TLS and IPsec

Selecting methods and parameters

Authentication

Keying (the secure exchange of secrets)

Ongoing communication

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Cipher Suite Key Negotiation Digital Signature Method Symmetric Key Encryption Method Hashing Method for HMAC Strength
NULL_WITH_NULL_NULL None None None None None
RSA_EXPORT_WITH_ RC4_40_MD5 RSA export strength (40 bits) RSA export strength (40 bits) RC4 (40-bit key) MD5 Weak
RSA_WITH_DES_CBC_ SHA RSA RSA DES_CBC SHA-1 Stronger but not very strong
DH_DSS_WITH_3DES_ EDE_CBC_SHA Diffie–Hellman Digital Signature Standard 3DES_ EDE_CBC SHA-1 Strong
RSA_WITH_AES_256_CBC_SHA256 RSA RSA AES 256 bits SHA-256 Very strong

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Copyright Pearson Prentice Hall 2013

3.1 What Is Cryptography

3.2 Symmetric Key Encryption Ciphers

3.3 Cryptographic System Standards

3.4 The Negotiation Stage

3.5 Initial Authentication Stage

3.6 The Keying Stage

3.7 Message-by-Message Authentication

3.8 Quantum Security

3.9 Cryptographic Systems

3.10 SSL/TLS and IPsec

Selecting methods and parameters

Authentication

Keying (the secure exchange of secrets)

Ongoing communication

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  • Hashing

A hashing algorithm is applied to a bit string of any length

The result of the calculation is called the hash

For a given hashing algorithm, all hashes are the same short length

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Bit string of any length

Hash: bit string of small fixed length

Hashing

Algorithm

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  • Hashing versus Encryption

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Characteristic Encryption Hashing
Result length About the same length as the plaintext Short fixed length regardless of message length
Reversible? Yes. Decryption No. There is no way to get from the short hash back to the long original message

  • Hashing Algorithms

MD5 (128-bit hashes)

SHA-1 (160-bit hashes)

SHA-224, SHA-256, SHA-384, and SHA-512 (name gives hash length in bits)

Note: MD5 and SHA-1 should not be used because have been shown to be unsecure

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Copyright Pearson Prentice Hall 2013

3.1 What Is Cryptography

3.2 Symmetric Key Encryption Ciphers

3.3 Cryptographic System Standards

3.4 The Negotiation Stage

3.5 Initial Authentication Stage

3.6 The Keying Stage

3.7 Message-by-Message Authentication

3.8 Quantum Security

3.9 Cryptographic Systems

3.10 SSL/TLS and IPsec

Selecting methods and parameters

Authentication

Keying (the secure exchange of secrets)

Ongoing communication

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  • There are two types of ciphers used for confidentiality

In symmetric key encryption for confidentiality, the two sides use the same key

For each dialogue (session), a new symmetric key is generated: the symmetric session key

In public key encryption, each party has a public key and a private key that are never changed

A person’s public key is available to anyone

A person keeps his or her private key secret

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  • The two parties exchange parameters p and g
  • Each uses a number that is never shared explicitly to compute a second number

Each sends the other their second number

  • Each does another computation on the second computed number
  • Both get the third number, which is the key
  • All of this communication is sent in the clear

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The gory details

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Copyright Pearson Prentice Hall 2013

3.1 What Is Cryptography

3.2 Symmetric Key Encryption Ciphers

3.3 Cryptographic System Standards

3.4 The Negotiation Stage

3.5 Initial Authentication Stage

3.6 The Keying Stage

3.7 Message-by-Message Authentication

3.8 Quantum Security

3.9 Cryptographic Systems

3.10 SSL/TLS and IPsec

Selecting methods and parameters

Authentication

Keying (the secure exchange of secrets)

Ongoing communication

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  • Consumes nearly all of the dialogues
  • Message-by-Message Encryption

Nearly always uses symmetric key encryption

Already covered

Public key encryption is too inefficient

  • Message-by-Message Authentication

Digital signatures

Message authentication codes (MACs)

Also provide message-by-message integrity

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Encryption is done to protect the plaintext

It is not needed for message-by-message authentication

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Point of frequent confusion

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Encryption Goal Sender Encrypts with Receiver Decrypts with
Public Key Encryption for Confidentiality The receiver’s public key The receiver’s private key
Public Key Encryption for Authentication The sender’s private key The True Party’s public key (not the sender’s public key)

  • Cannot use the sender’s public key

It would always “validate” the sender’s digital signature

  • Normally requires a digital certificate

File provided by a certificate authority (CA)

The certificate authority must be trustworthy

Digital certificate provides the subject’s (True Party’s) name and public key

Don’t confuse digital signatures and the digital certificates used to test digital signatures!

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Certificate provides the True Party’s public key

Serial number allows the receiver to check if the digital certificate has been revoked by the CA

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Field Description
Version Number Version number of the X.509 standard. Most certificates follow Version 3. Different versions have different fields. This figure reflects the Version 3 standard.
Issuer Name of the Certificate Authority (CA).
Serial Number Unique serial number for the certificate, set by the CA.
Subject (True Party) The name of the person, organization, computer, or program to which the certificate has been issued. This is the true party.
Public Key The public key of the subject (the true party).
Public Key Algorithm The algorithm the subject uses to sign messages with digital signatures.

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The CA signs the cert with its own private key so that the cert’s validity can be checked for alterations.

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Field Description
Digital Signature The digital signature of the certificate, signed by the CA with the CA’s own private key. For testing certificate authentication and integrity. User must know the CA’s public key independently.
Signature Algorithm Identifier The digital signature algorithm the CA uses to sign its certificates.
Other Fields

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  • Testing the Digital Signature

The digital certificate has a digital signature of its own

Signed with the Certificate Authority’s (CA’s) private key

Must be tested with the CA’s well-known public key

If the test works, the certificate is authentic and unmodified

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  • Checking the Valid Period

Certificate is valid only during the valid period in the digital certificate (not shown in the figure)

If the current time is not within the valid period, reject the digital certificate

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  • Checking for Revocation

Certificates may be revoked for improper behavior or other reasons

Revocation must be tested

Cannot be done by looking at fields within the certificate

Receiver must check with the CA

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  • Checking for Revocation

Verifier may download the entire certificate revocation list from the CA

See if the serial number is on the certificate revocation list

If so, do not accept the certificate

Or, the verifier may send a query to the CA

Requires the CA to support the Online Certificate Status Protocol

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  • Also Brings Message Integrity

If the message has been altered, the authentication method will fail automatically

  • Digital Signature Authentication

Uses public key encryption for authentication

Very strong but expensive

  • Key-Hashed Message Authentication Codes

An alternate authentication method using hashing

Much less expensive than digital signature authentication

Much more widely used

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As in the case of digital signatures, confidentiality is done to protect the plaintext.

It is not needed for authentication and has nothing to do with authentication.

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  • Nonrepudiation means that the sender cannot deny that he or she sent a message
  • With digital signatures, the sender must use his or her private key

It is difficult to repudiate that you sent something if you use your private key

  • With HMACs, both parties know the key used to create the HMAC

The sender can repudiate the message, claiming that the receiver created it

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  • However, packet-level nonrepudiation is unimportant in most cases
  • The application message—an e-mail message, a contract, etc., is the important thing
  • If the application layer message has its own digital signature, you have nonrepudiation for the application message, even if you use HMACs at the Internet layer for packet authentication

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  • Replay Attacks

Capture and then retransmit an encrypted message later

May have a desired effect

Even if the attacker cannot read the message

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  • Thwarting Replay Attacks

Time stamps to ensure freshness of each message

Sequence numbers so that repeated messages can be detected

Nonces

Unique randomly generated number placed in each request message

Reflected in the response message

If a request arrives with a previously used nonce, it is rejected

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Confidentiality Authentication
Symmetric Key Encryption Applicable. Sender encrypts with key shared with the receiver. Not applicable.
Public Key Encryption Applicable. Sender encrypts with receiver’s public key. Receiver decrypts with the receiver’s own private key. Applicable. Sender (supplicant) encrypts with own private key. Receiver (verifier) decrypts with the public key of the true party, usually obtained from the true party’s digital certificate.
Hashing Not applicable. Applicable. Used in MS-CHAP for initial authentication and in HMACs for message-by-message authentication.

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3.1 What Is Cryptography

3.2 Symmetric Key Encryption Ciphers

3.3 Cryptographic System Standards

3.4 The Negotiation Stage

3.5 Initial Authentication Stage

3.6 The Keying Stage

3.7 Message-by-Message Authentication

3.8 Quantum Security

3.9 Cryptographic Systems

3.10 SSL/TLS and IPsec

  • Quantum Mechanics

Describes the behavior of fundamental particles

Complex and even weird results

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  • Quantum Key Distribution

Transmits a very long key—as long as the message

This is a one-time key that will not be used again

A one-time key as long as a message cannot be cracked by cryptanalysis

If an interceptor reads part of the key in transit, this will be immediately apparent to the sender and receiver

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  • Quantum Key Cracking

Tests many keys simultaneously

If quantum key cracking becomes capable of working on long keys, today’s strong key lengths will offer no protection

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3.1 What Is Cryptography

3.2 Symmetric Key Encryption Ciphers

3.3 Cryptographic System Standards

3.4 The Negotiation Stage

3.5 Initial Authentication Stage

3.6 The Keying Stage

3.7 Message-by-Message Authentication

3.8 Quantum Security

3.9 Cryptographic Systems

3.10 SSL/TLS and IPsec

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Copyright Pearson Prentice Hall 2013

3.1 What Is Cryptography

3.2 Symmetric Key Encryption Ciphers

3.3 Cryptographic System Standards

3.4 The Negotiation Stage

3.5 Initial Authentication Stage

3.6 The Keying Stage

3.7 Message-by-Message Authentication

3.8 Quantum Security

3.9 Cryptographic Systems

3.10 SSL/TLS and IPsec

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SSL/TLS IPsec
Cryptographic security standard Yes Yes
Cryptographic security protections Good Gold Standard
Supports central management No Yes
Complexity and expense Lower Higher
Layer of operation Transport Internet
Transparently protects all higher-layer traffic No Yes
Works with IPv4 and IPv6 NA Yes
Modes of operation NA Transport, Tunnel

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1.

End-to-End

Security

(Good)

2.

Security in
Site Network

(Good)

3.

Setup Cost

On Each Host

(Costly)

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2.

No Security in
Site Network

(Bad)

3.

No Setup Cost

On Each Host

(Good)

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Characteristic Transport Mode Tunnel Mode
Uses an IPsec VPN Gateway? No Yes
Cryptographic Protection All the way from the source host to the destination host, including the Internet and the two site networks. Only over the Internet between the IPsec gateways. Not within the two site networks.
Setup Costs High. Setup requires the creation of a digital certificate for each client and significant configuration work. Low. Only the IPsec gateways must implement IPsec, so only they need digital certificates and need to be configured.

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Characteristic Transport Mode Tunnel Mode
Firewall Friendliness Bad. A firewall at the border to a site cannot filter packets because the content is encrypted. Good. Each packet is decrypted by the IPsec gateway. A border firewall after the IPsec gateway can filter the decrypted packet.
The “Bottom Line” End-to-end security at high cost. Low cost and protects the packet over the most dangerous part of its journey.

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