Practical Crypto Attacks Against Web Applications

Against Web Applications

Justin Clarke

!  IANAC

!  Usage != security

!  Pentesting?

2

!  Confidentiality – Prevent the disclosure of
information to unauthorized individuals or
systems

!  Integrity – Ensure that data cannot be
modified undetectably

!  Authenticity - Validate that a party is who
they claim they are

3

!  Symmetric Crypto Attacks
!  ECB Mode Usage
!  Padding-Based Attacks

!  Secure Random Number Generation

4

!  Most block ciphers support multiple modes of
operation

!  The most common modes are :
!  ECB – Electronic Code Book
!  CBC – Cipher Block Chaining
!  CFB - Cipher Feedback
!  OFB - Output Feedback

!  None provide integrity if used in isolation

5

!  Reason #1

ECB

CONFIDENTIALITY

7

!  Reason #2

UID:23909,Email:john@doe.com,NickName:JohnDoe2301,Role:3

8

!  Reason #2
Block 1 Block 2 Block 3 Block 4 Block 5 Block 6 Block 7
UID:2390 9,Email: john@doe .com,Nic kName:Jo hnDoe230 1,Role:3
CIPHERTEX 9648dab1 22a1eaee 0f5a7a2a 86adfcf6 6adb7872 96bdc238 69e75f87
T
d7f285ac db7aabbb 1f8de75f 17abcbcf 7ab9dd8e 5fa70ba2 cf74ab6d


9

!  Reason #2
T


CIPHERTEX 9648dab1 69e75f87 22a1eaee 0f5a7a2a 86adfcf6 6adb7872 96bdc238
T
d7f285ac cf74ab6d db7aabbb 1f8de75f 17abcbcf 7ab9dd8e 5fa70ba2

10

!  Reason #2
T


T
UID:2390 1,Role:3 9,Email: john@doe .com,Nic kName:Jo hnDoe230

UID:23901,Role:39,Email:john@doe.com,NickName:JohnDoe230

11

!  Reason #2
T


T
UID:2390 1,Role:3 9,Email: john@doe .com,Nic kName:Jo hnDoe230

UID:23901,Role:39,Email:john@doe.com,NickName:JohnDoe230

12

CBC

CONFIDENTIALITY

15

!  Original Ciphertext

BLOCK 1 BLOCK 2 BLOCK 3

16

!  Block Swapping will result in data corruption

BLOCK 1 BLOCK 3 BLOCK 2

17

!  “Padding Oracle” Attack

!  Leverages byte flipping of ciphertext to generate
invalid padding exceptions

!  Data can be decrypted (and encrypted too) without
knowledge of the secret key

18

!  Assuming this scheme, then there are only 8
possible valid padding sequences:
!  0x01
!  0x02, 0x02
!  0x03, 0x03, 0x03,
!  0x04, 0x04, 0x04, 0x04
!  0x05, 0x05, 0x05, 0x05, 0x05,
!  0x06, 0x06, 0x06, 0x06, 0x06, 0x06
!  0x07, 0x07, 0x07, 0x07, 0x07, 0x07, 0x07
!  0x08, 0x08, 0x08, 0x08, 0x08, 0x08, 0x08, 0x08

20

!  Is the key the correct size?
!  Invalid Key Exception

!  Is the value (bytes) an even block multiple?
!  Invalid Length Exception

!  Is the decrypted block properly padded?
!  Invalid Padding Exception CRITICAL

!  Return the value

22

Call this “Byte X”

Call this “Byte Y”
Basic Premise:
•  A change of Byte X (ciphertext) will change Byte Y (plaintext)
•  There is a one-to-one correlation between Byte X values and Byte Y values
•  Exception is thrown if plain-text does not end with a valid padding sequence

24

Byte X == 0x00

Byte Y == ???
Exception? YES
•  Byte Y is not valid padding

25

Byte X == 0x01

Byte Y == ???
Exception? YES
•  Byte Y is not valid padding

26

Byte X == 0x02

Byte Y == ???
Exception? YES
•  Byte Y IS valid padding (must be 0x01)

27

!  What does that tell us?

!  The altered byte value produced valid padding when
XOR’ed with the intermediate value

IF A ^ B = C

THEN A ^ C = B
AND C ^ B = A

28

!  What does that tell us?

!  If the padding byte was 0x01:
!  Our Byte (0x02) ^ Intermediate Byte (??) == 0x01
!  Intermediate Byte == Our Byte (0x02) ^ 0x01

!  The plain-text value is the intermediate value
XOR’ed with the prior ciphertext byte

29

!  As we’ve seen, encrypted data (while kept
private) is still susceptible to tampering

Message

Encryption

!  We need to ensure PRIVACY and INTEGRITY

31

!  Encrypt + Sign the Ciphertext

Message
SIGNATURE
Encryption

!  HMAC: Combines a cryptographic hash function
with a secret key
!  Cannot be re-computed without the key

!  Verifies the integrity and authenticity of a message

32

!  Why not HMAC within the ciphertext?
!  Does not prevent against side channel attacks
during decryption

!  Padding Oracle Attack in .NET Framework
!  Discovered September 2010
!  Viewstate and Forms Authentication Cookies were affected
even though an HMAC was included within the ciphertext
!  Tampering was only be detected after decryption

33

!  When do you need a random number?

!  Password Generator, Encryption Keys, Session
Identifiers, etc…

!  How random is “random”?

Pseudo Random Number Generator
vs.
Cryptographically Secure Random Number Generator

34

!  Two common attacks against RNG’s

!  Non-random Seed Values

!  Formula used to produce random numbers

35

!  What do you think this code will produce?
// Generate First Series
byte[] bytes1 = new byte[100];
Random rnd1 = new Random();
rnd1.NextBytes(bytes1);
Console.WriteLine("First Series:");
for (int ctr = bytes1.GetLowerBound(0); ctr <= bytes1.GetUpperBound(0); ctr++) {
Console.Write("{0, 5}", bytes1[ctr]);
if ((ctr + 1) % 10 == 0) Console.WriteLine();
}

// Generate Second Series
byte[] bytes2 = new byte[100];
Random rnd2 = new Random();
rnd2.NextBytes(bytes2);
Console.WriteLine("Second Series:");
for (int ctr = bytes2.GetLowerBound(0); ctr <= bytes2.GetUpperBound(0); ctr++) {
Console.Write("{0, 5}", bytes2[ctr]);
if ((ctr + 1) % 10 == 0) Console.WriteLine();
}

36

!  Output from the previous code
First Series:
97 129 149 54 22 208 120 105 68 177
113 214 30 172 74 218 116 230 89 18
12 112 130 105 116 180 190 200 187 120
7 198 233 158 58 51 50 170 98 23
21 1 113 74 146 245 34 255 96 24
232 255 23 9 167 240 255 44 194 98
18 175 173 204 169 171 236 127 114 23
167 202 132 65 253 11 254 56 214 127
145 191 104 163 143 7 174 224 247 73
52 6 231 255 5 101 83 165 160 231
Both series
Second Series: are identical
97 129 149 54 22 208 120 105 68 177
113 214 30 172 74 218 116 230 89 18
12 112 130 105 116 180 190 200 187 120
7 198 233 158 58 51 50 170 98 23
21 1 113 74 146 245 34 255 96 24
232 255 23 9 167 240 255 44 194 98
18 175 173 204 169 171 236 127 114 23
167 202 132 65 253 11 254 56 214 127
145 191 104 163 143 7 174 224 247 73
52 6 231 255 5 101 83 165 160 231

37

!  If you don’t seed the random number
generator, it will automatically be seeded

!  With what?

“By default, the parameterless constructor of the Random class
uses the system clock to generate its seed value”

http://msdn.microsoft.com/en-us/library/system.random.aspx

38

!  What if this code was in ResetPassword.aspx?
StringBuilder password = new StringBuilder();

// Define all upper and lower chars with special chars
char[] lCase = new char[] { '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', '!', '@', '#', '$', '%', '^', '&', '*', '(', ')', '-', '_' };

int lCaseIndex = 0;

Random rand = new Random();

// Randomly select 12 characters from the values above
for (int cnt = 0; cnt < 12; cnt++)
{
lCaseIndex = rand.Next(0, lCase.Length - 1);
password.Append(lCase[lCaseIndex]);
}

string newPassword = password.ToString();

39

!  Seed Race Condition Attack (Seed Racing)

!  Based on a research experiment conducted in 2008

!  67,000 HTTP requests to a server with a random
password generator similar to the one shown

!  Results: 208 unique passwords

!  322 duplicated in one or more accounts

40

!  Is Java.Random any better?

!  Uses a Linear Congruential Formula for
generating random data (LCG)

One Dimensional LCG Plot

41

!"#$%&'(()*&
+$,-(.&%(&
./01&

43

!2#((3*4&5&
6(7$&6(8&
9:/001&

45

!  Crypto is hard to get right
!  Lots of ways to make mistakes

!  When in doubt, ask an expert

46

Practical Crypto Attacks Against Web Applications

Recommended

Recommended

More Related Content

Similar to Practical Crypto Attacks Against Web Applications

Similar to Practical Crypto Attacks Against Web Applications (20)

More from Security BSides London

More from Security BSides London (12)

Recently uploaded

Recently uploaded (20)

Practical Crypto Attacks Against Web Applications