Assignment 6

Deadline Friday, March 13, 2020 by 23:59:59

Early Turn-In: Wednesday, March 11, 2020 by 23:59:59


In this project, we'll start by investigating Vigenere ciphers, then move on to investigating vulnerabilities in widely used cryptographic hash functions, including length-extension attacks and collision vulnerabilities, and an implementation vulnerability in a popular digital signature scheme.

Part 1: Vigenere ciphers

For this problem, solve by hand or write a program (perhaps in Python).

You can read about how the Vigenere cipher works on Wikipedia. Vigenere ciphers can be generally deciphered using Kasiski Examination, which is discussed on the wikipedia page.

You can find some ciphertext produced with the Vigenere cipher under a certain key on Gradescope as the assignment "Assignment 6 ciphertext".

Assume that encrypting the letter A with the key results in no change, encrypting the letter B results in an increment by one place in the alphabet, encrypting C resulting in an increment by two places, etc. Also assume that the original plaintext contains only uppercase letters (A-Z) and no spaces or punctuation.

What is the key?

What to submit A text file named vigenere.key containing your key.

Historical note: This November, it was discovered that the security company Fortinet was using "XOR encryption with a static key" in some products, which is similar to a Vigenere cipher and has similar (lack of) security properties.

Part 2: Length extension

In most applications, you should use MACs such as HMAC-SHA256 instead of plain cryptographic hash functions (e.g., MD5, SHA-1, or SHA-256) because hashes, also known as digests, fail to match our intuitive security expectations. What we really want is something that behaves like a pseudorandom function, which HMACs seem to approximate and hash functions do not.

One difference between hash functions and pseudorandom functions is that many hashes are subject to length extension. Many common hash functions use a design called the Merkle-Damgard construction. Each is built around a compression function f and maintains an internal state s, which is initialized to a fixed constant. Messages are processed in fixed-size blocks by applying the compression function to the current state and current block to compute an updated internal state, i.e., s_{i+1} = f(s_i, b_i). The result of the final application of the compression function becomes the output of the hash function.

A consequence of this design is that if we know the hash of an n-block message, we can find the hash of longer messages by applying the compression function for each block b_{n+1}, b_{n+2}, ... that we want to add. This process is called length extension, and it can be used to attack many applications of hash functions.

2a. Experimenting

To experiment with this idea, we'll use a Python implementation of the MD5 hash function, though SHA-1 and SHA-256 are vulnerable to length extension in the same way. You can download the pymd5 module here and learn how to use it by running pydoc pymd5. To follow along with these examples, run Python in interactive mode and run the command from pymd5 import md5, padding.

Consider the string "Use HMAC, not hashes". We can compute its MD5 hash by running:

from pymd5 import md5, padding
m = "Use HMAC, not hashes"
h = md5()

or, more compactly,


The output should be 3ecc68efa1871751ea9b0b1a5b25004d.

MD5 processes messages in 512-bit blocks, so internally, the hash function pads m to a multiple of that length. The padding consists of the bit 1, followed by as many 0 bits as necessary, followed by a 64-bit count of the number of bits in the unpadded message. (If the 1 and the count won't fit in the current block, an additional block is added.) You can use the function padding(count) in the pymd5 module to compute the padding that will be added to a count-bit message.

Even if we didn't know m, we could compute the hash of longer messages of the general form m + padding(len(m)*8) + suffix by setting the initial internal state of our MD5 function to MD5(m), instead of the default initialization value, and setting the function's message length counter to the size of m plus the padding (a multiple of the block size). To find the padded message length, guess the length of m and run bits = (length_of_m + len(padding(length_of_m * 8))) * 8.

The pymd5 module lets you specify these parameters as additional arguments to the md5 object:

h = md5(state=codecs.decode("3ecc68efa1871751ea9b0b1a5b25004d", "hex"), count=512)

Now you can use length extension to find the hash of a longer string that appends the suffix "Good advice". Simply run:

x = "Good advice"

to execute the compression function over x and output the resulting hash. Verify that it equals the MD5 hash of m + padding(len(m)*8) + x. Notice that, due to the length-extension property of MD5, we didn't need to know the value of m to compute the hash of the longer string - all we needed to know was m's length and its MD5 hash.

This part of the assignment is intended to introduce length extension and familiarize you with the Python MD5 module we will be using; you will not need to submit anything for it.

2b. Conduct a length extension attack

Length extension attacks can cause serious vulnerabilities when people mistakenly try to construct something like an HMAC by using hash(secret || message). The National Bank of CSE 127, which is not up-to-date on its security practices, hosts an API that allows its client-side applications to perform actions on behalf of a user by loading URLs of the form:

where token is MD5(user's 8-character password || user=... [the rest of the decoded URL starting from user= and ending with the last command]).

Using the techniques that you learned in the previous section and without guessing the password, apply length extension to create a URL ending with &command3=UnlockAllSafes that would be treated as valid by the server API.

Note: Because of its bad security practices, the National Bank of CSE 127 has taken down its website. So you'll have to use gradescope to test if your attack URL would work.

Hint: You might want to use the quote() function from Python's urllib.parse module to encode non-ASCII characters in the URL.

Historical fact: In 2009, security researchers found that the API used by the photo-sharing site Flickr suffered from a length-extension vulnerability almost exactly like the one in this exercise.

What to submit A Python 3.x script named that:

  1. Accepts a valid URL in the same form as the one above as a command line argument.
  2. Modifies the URL so that it will execute the UnlockAllSafes command as the user.
  3. Prints the new URL to the command line.

You should make the following assumptions:

  • The input URL will have the same form as the sample above, but we may change the server hostname and the values of token, user, command1, and command2. These values may be of substantially different lengths than in the sample.

  • The input URL may be for a user with a different password, but the length of the password will be unchanged.

You can base your code on the following example:

import sys, urllib.parse
from pymd5 import md5, padding
url = sys.argv[1]

# Your code to modify url goes here


Part 3: MD5 collisions

MD5 was once the most widely used cryptographic hash function, but today it is considered dangerously insecure. This is because cryptanalysts have discovered efficient algorithms for finding collisions---pairs of messages with the same MD5 hash value.

The first known collisions were announced on August 17, 2004 by Xiaoyun Wang, Dengguo Feng, Xuejia Lai, and Hongbo Yu. Here's one pair of colliding messages they published:

Message 1:

d131dd02c5e6eec4693d9a0698aff95c 2fcab58712467eab4004583eb8fb7f89
55ad340609f4b30283e488832571415a 085125e8f7cdc99fd91dbdf280373c5b
d8823e3156348f5bae6dacd436c919c6 dd53e2b487da03fd02396306d248cda0
e99f33420f577ee8ce54b67080a80d1e c69821bcb6a8839396f9652b6ff72a70

Message 2:

d131dd02c5e6eec4693d9a0698aff95c 2fcab50712467eab4004583eb8fb7f89
55ad340609f4b30283e4888325f1415a 085125e8f7cdc99fd91dbd7280373c5b
d8823e3156348f5bae6dacd436c919c6 dd53e23487da03fd02396306d248cda0
e99f33420f577ee8ce54b67080280d1e c69821bcb6a8839396f965ab6ff72a70

Copy the above hex strings into file1.hex and file2.hex. Convert each group of hex strings into a binary file. (On Linux, run xxd -r -p file.hex > file.)

  1. What are the MD5 hashes of the two binary files? Verify that they're the same. (openssl dgst -md5 file1 file2)
  2. What are their SHA-256 hashes? Verify that they're different. (openssl dgst -sha256 file1 file2)

You don't need to submit anything for the above questions.

3a. Generating collisions yourself

In 2004, Wang's method took more than 5 hours to find a collision on a desktop PC. Since then, researchers have introduced vastly more efficient collision finding algorithms. You can compute your own MD5 collisions using a tool written by Marc Stevens that uses a more advanced technique.

You can download the fastcoll tool here: (Windows executable)

or (source code)

If you are compiling fastcoll from source, you can compile using this makefile. You will also need to have installed the Boost libraries. On Ubuntu, you can install using apt-get install libboost-all-dev. On OS X, you can install Boost via the Homebrew package manager using brew install boost.

  1. Generate your own collision with this tool. How long did it take? (time ./fastcoll -o file1 file2)

  2. What are your files? To get a hex dump, run xxd -p file.

  3. What are their MD5 hashes? Verify that they're the same.

  4. What are their SHA-256 hashes? Verify that they're different.

What to submit Write your answers in writeup.txt. This file will also be used for part 5.

3b. A hash collision attack

The collision attack lets us generate two messages with the same MD5 hash and any chosen (identical) prefix. Due to MD5's length-extension behavior, we can append any suffix to both messages and know that the longer messages will also collide. This lets us construct files that differ only in a binary "blob" in the middle and have the same MD5 hash, i.e. prefix || blobA || suffix and prefix || blobB || suffix.

We can leverage this to create two programs (shell scripts) that have identical MD5 hashes but wildly different behaviors. We're using shell scripts, but this could be done using a program in almost any language. Put the following two lines into a file called prefix:

cat << "EOF" | openssl dgst -sha256 > DIGEST

and put these four lines (starting with a blank line) into a file called suffix:

digest=$(cat DIGEST | sed 's/(stdin)= //' )
echo "The sha256 digest is $digest"

Now use fastcoll to generate two files with the same MD5 hash that both begin with prefix. (fastcoll -p prefix -o col1 col2.) Then append the suffix to both (cat col1 suffix >; cat col2 suffix > Verify that and have the same MD5 hash but generate different output.

Extend this technique to produce another pair of programs, good and evil, that also share the same MD5 hash. One program should execute a benign payload: echo or print "I mean no harm." The second should execute a pretend malicious payload: echo or print "You are doomed!"

What to submit Two scripts, good and evil, that have the same MD5 hash, have different SHA-256 hashes, and print the specified messages.

Part 4: RSA signature forgery

A secure implementation of RSA encryption or digital signatures requires a proper padding scheme. RSA without padding, also known as textbook RSA, has several undesirable properties. For example, it is trivial for an attacker with only an RSA public key pair (n,e) to produce a mathematically valid message, signature pair by choosing an s and returning (s^e, s).

In order to prevent an attacker from being able to forge valid signatures in this way, RSA implementations use a padding scheme to provide structure to the messages that are encrypted or signed. The most commonly used padding scheme in practice is defined by the PKCS #1 v1.5 standard, which can be found at The standard defines, among other things, the format of RSA keys and signatures and the procedures for generating and validating RSA signatures.

4a. Validating RSA signatures

You can experiment with validating RSA signatures yourself. Create a file called that contains the following RSA public key:

-----END PUBLIC KEY-----

You can view the modulus and public exponent of this key by running:

openssl rsa -in -pubin -text -noout

Create a file containing only the text CSE 127 rul3z!.

echo -n 'CSE 127 rul3z!' > message

The following is a base64-encoded signature of the file message using the public key above.


Convert this signature into a binary file:

base64 -d -i sig.b64 > sig

Now verify the signature against the file you created.

openssl dgst -sha1 -verify -signature sig message

We can also use basic math operations in Python to explore this signature further. Remember, RSA ciphertexts, plaintexts, exponents, moduli, and signatures are actually all integers.

Open a Python shell and run the following commands to import the signature as an integer:

from Crypto.PublicKey import RSA
from Crypto.Hash import SHA
signature = int(open('sig', 'rb').read().hex(), 16)

Next, import the public key file that you created earlier:

pubkey = RSA.importKey(open('').read())

The modulus and exponent are then accessible as pubkey.n and pubkey.e, respectively. Now reverse the signing operation and examine the resulting value in hex:

"{:0128x}".format(pow(signature, pubkey.e, pubkey.n))

You should see something like '0001fffff ... 22c1422dac3c4e5fdd87040b3fb156acd3d83d1f' Verify that the last 20 bytes of this value match the SHA-1 hash of your file:"CSE 127 rul3z!").hexdigest()

You don't need to submit anything for this part.

4b. PKCS #1 v1.5 signature padding

The signed value you examined in the previous section had been padded using the PKCS #1 v1.5 signature scheme. PKCS #1 v1.5 padding for RSA signatures is structured as follows: one 00 byte, one 01 byte, some FF bytes, another 00 byte, some special ASN.1 bytes denoting which hash algorithm was used to compute the hash digest, then the bytes of the hash digest itself. The number of FF bytes varies such that the size of m is equal to the size of the RSA key.

A k-bit RSA key used to sign a SHA-1 hash digest will generate the following padded value of m:

  00 01 FF...FF 00 3021300906052B0E03021A05000414 XX...XX
        ^^^^^^^    ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^
    k/8 - 38 bytes wide         ||            20-byte SHA-1 digest
                        ASN.1 "magic" bytes

When PKCS padding is used, it is important for implementations to verify that every bit of the padded, signed message is exactly as it should be. It is tempting for an implementer to validate the signature by first stripping off the 00 01 bytes, then some number of padding FF bytes, then 00, and then parse the ASN.1 and verify the hash. If the implementation does not check the length of the FF bytes and that the hash is in the least significant bits of the message, then it is possible for an attacker to forge values that pass this validation check.

This possibility is particularly troubling for signatures generated with e = 3. If the length of the required padding, ASN.1 bytes, and hash value is significantly less than n^{1/3} then an attacker can construct a cube root over the integers whose most significant bits will validate as a correct signature, ignoring the actual key. To construct a "signature" that will validate against such implementations, an attacker simply needs to construct an integer whose most significant bytes have the correct format, including the hashed message, pad the remainder of this value with zeros or other garbage that will be ignored by the vulnerable implementation, and then take a cube root over the integers, rounding as appropriate.

4c. Constructing forged signatures

The National Bank of CSE 127 has a website that its employees use to initiate wire transfers between bank accounts. To authenticate each transfer request, the control panel requires a signature from a particular 2048-bit RSA key:

-----END PUBLIC KEY-----

Unfortunately, this control panel is running old software that has not been patched to fix the signature forgery vulnerability.

Using the signature forgery technique described above, produce an RSA signature that validates against the National Bank of CSE 127 site.

Historical fact: This attack was discovered by Daniel Bleichenbacher, who presented it in a lightning talk at the rump session at the Crypto 2006 conference. His talk is described in this mailing list posting: At the time, many important implementations of RSA signatures were discovered to be vulnerable to this attack, including OpenSSL. In 2014, the Mozilla library NSS was found to be vulnerable to this type of attack:

What to submit A Python 3.x script called that:

  1. Accepts a double-quoted string as command-line argument.
  2. Prints a base64-encoded forged signature of the input string.

We have provided a Python library,, that provides several useful functions that you may wish to use when implementing your solution. You can download the library here. Your program may assume that PyCrypto and are available, and may use standard Python libraries, but should otherwise be self-contained.

In order to use these functions, you will have to import You may wish to use the following template:

from Crypto.PublicKey import RSA
from Crypto.Hash import SHA
from roots import *
import sys

message = sys.argv[1]

# Your code to forge a signature goes here.

# some example functions from roots
root, is_exact = integer_nthroot(27, 3)

5. Writeup

  1. With reference to the construction of HMAC, explain how changing the design of the API in 2b to use token=HMAC(_user's password_)(user=...) would avoid the length extension vulnerability.

  2. Briefly explain why the technique you explored in 3b poses a danger to systems that rely on digital signatures to verify the integrity of programs before they are installed or executed. Examples include Microsoft Authenticode and most Linux package managers. (Assume that these systems sign MD5 hashes of the programs.)

  3. Since 2010, NIST has specified that RSA public exponents must be at least 2^16 + 1. Briefly explain why Bleichenbacher's attack would not work for these keys.

What to submit Write your answers in writeup.txt.

Submission Checklist

Submit the following to gradescope:

  • vigenere.key to Assignment 6 vigenere key (for part 1)

  • good and evil to Assignment 6 hash collision (for part 3)

  • to Assignment 6 length extension (for part 2)

  • to Assignment 6 signature forgery (for part 4)

  • writeup.txt to Assignment 6 writeup (with answers to parts 3a and 5)