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# Homework 5: Hash Function and Public Key Cryptography

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CSCE 465 Computer and Network Security 1
Homework 5: Hash Function and Public Key Cryptography
1 Overview
The learning objective of this homework is for students to get familiar with the concept and application of
one-way hash functions and Public-Key cryptography. To achieve the objective, the students will do both
theory (paper-and-pencil problems) and practice (programming and lab). After finishing the homework, in
addition to gaining a deeper understanding of the concepts, students should be able to use tools and write
programs to apply the learned knowledge.
2 Paper-and-Pencil Problems [40 pts]
There are a total of 4 paper-and-pencil problems from the KPS textbook (X.Y. means number Y homework
• 5.3. (8 pts)
• 5.4. (8 pts)
• 5.14. (8 pts)
• 6.2. (8 pts)
• 6.8. (8 pts)
3 Lab and Programming Tasks [60 + 10 bonus pts]
We will use the same OpenSSL lab environment as before. OpenSSL Command-Line HOWTO can be
3.1 Task 1: Generating Message Digest and MAC [7 pts]
In this task, we will play with various one-way hash algorithms. You can use the following openssl
dgst command to generate the hash value for a file. To see the manuals, you can type man openssl and
man dgst.
% openssl dgst dgsttype filename
Please replace the dgsttype with a specific one-way hash algorithm, such as -md5, -sha1, -sha256,
etc. In this task, you should try at least 3 different algorithms, and describe your observations. You can find
the supported one-way hash algorithms by typing “man openssl”.
3.2 Task 2: Keyed Hash and HMAC [9 pts]
In this task, we would like to generate a keyed hash (i.e. MAC) for a file. We can use the -hmac option
(this option is currently undocumented, but it is supported by openssl). The following example generates
a keyed hash for a file using the HMAC-MD5 algorithm. The string following the -hmac option is the key.
CSCE 465 Computer and Network Security 2
% openssl dgst -md5 -hmac “abcdefg” filename
Please generate a keyed hash using HMAC-MD5, HMC-SHA256, and HMAC-SHA1 for any file that
you choose. Please try several keys with different length. Do we have to use a key with a fixed size in
HMAC? If so, what is the key size? If not, why?
3.3 Task 3: The Randomness of One-way Hash [9 pts]
To understand the properties of one-way hash functions, we would like to do the following exercise for MD5
and SHA256:
1. Create a text file of any length.
2. Generate the hash value H1 for this file using a specific hash algorithm.
3. Flip one bit of the input file. You can achieve this modification using ghex.
4. Generate the hash value H2 for the modified file.
5. Please observe whether H1 and H2 are similar or not. Please describe your observations in the report.
You can write a short program to count how many bits are the same between H1 and H2.
3.4 Task 4: Hash Collision-Free Property [20+10 bonus pts]
In this task, we will investigate hash function’s collision-free properties. We will use the brute-force
method to see how long it takes to break these properties. Instead of using openssl’s command-line
tools, you are required to write your own C programs to invoke the message digest functions in openssl’s
crypto library. A sample code can be found from http://www.openssl.org/docs/crypto/EVP_
DigestInit.html. Please get familiar with this sample code.
Since most of the hash functions are quite strong against the brute-force attack on those two properties,
it will take us years to break them using the brute-force method. To make the task feasible, we reduce the
length of the hash value to 24 bits. We can use any one-way hash function, but we only use the first 24 bits
of the hash value in this task. Namely, we are using a modified one-way hash function. Please design an
experiment to find out the following:
1. How many trials it will take you to find two messages with the same hash values using the brute-force
method? You should repeat your experiment for multiple times, and report your average number of
trials.
2. How many trials it will take you to find a message has the same hash value as a given/known message’s
hash value using the brute-force method? Similarly, you should report the average.
3. Based on your observation, which case is easier to break using the brute-force method?
4. (10 Bonus Points) Can you explain the difference in your observation mathematically (i.e., a formal
proof)?
CSCE 465 Computer and Network Security 3
3.5 Task 5: Performance Comparison: RSA versus AES [8 pts]
In this task, we will study the performance of public-key algorithms. Please prepare a file (message.txt)
that contains a 16-byte message. Please also generate an 1024-bit RSA public/private key pair. Then, do the
following:
1. Encrypt message.txt using the public key; save the the output in message enc.txt.
2. Decrypt message enc.txt using the private key.
3. Encrypt message.txt using a 128-bit AES key.
4. Compare the time spent on each of the above operations, and describe your observations. If an operation is too fast, you may want to repeat it for many times, and then take an average.
After you finish the above exercise, you can now use OpenSSL’s speed command to do such a benchmarking. Please describe whether your observations are similar to those from the outputs of the speed
command. The following command shows examples of using speed to benchmark rsa and aes:
% openssl speed rsa
% openssl speed aes
3.6 Task 6: Create Digital Signature [7 pts]
In this task, we will use OpenSSL to generate digital signatures. Please prepare a file (example.txt) of
any size. Please also prepare an RSA public/private key pair. Do the following:
1. Sign the SHA256 hash of example.txt; save the output in example.sha256.
2. Verify the digital signature in example.sha256.
3. Slightly modify example.txt, and verify the digital signature again.
Please describe how you did the above operations (e.g., what commands do you use, etc.). Explain your
observations. Please also explain why digital signatures are useful.
4 Submission
You need to submit a detailed homework report (as well as any required program) to describe what you
have done and what you have observed; you also need to provide explanation to the observations that are
interesting or surprising. In your report, you need to answer all the questions listed in this homework.

Homework 5: Hash Function and Public Key Cryptography
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