Assignment 2

Assigned: 23/10/2020
Due: 30/10/2020

In this assignment you are going to develop a symmetric encryption tool in C, using the
OpenSSL toolkit. The purpose of this assignment is to provide you the opportunity to get
familiar with the very popular general-purpose cryptography toolkit and acquire hands-on
experience in implementing simple cryptographic applications. The tool will provide encryption,
decryption, CMAC signing and CMAC verification functionality.

More specifically, you are going to use the EVP API, found in the OpenSSL toolkit, which
provides a high-level interface to cryptographic functions. The cryptographic algorithm you are
going to use is AES in Electronic Code Book (ECB) mode with both 128 and 256 bit modes.

Task A
[Key Derivation Function (KDF)]
In this task you have to implement a key derivation function. The function derives the symmetric
key from a user-defined string (password). In order to generate the key you will use the
appropriate functions from the EVP API and the SHA1 cryptographic hash function. The KDF
requires as arguments the password and the desired key size (128 or 256 bits) and generates a
symmetric key of the appropriate size.

Task B
[Data Encryption]
Develop a function that provides AES-ECB encryption functionality, using 128-bit and 256-bit
keys. This function reads the data of an input file and encrypts them using AES-ECB with the
key generated by the KDF described in Task A. Then, it stores the ciphertext to an output file.
Use the EVP API in order to develop the encryption functionality.

Task C
[Data Decryption]
Using the EVP API, implement a function that reads a ciphertext from an input file and decrypts
it with AES-ECB using 128-bit or 256-bit keys. The key will be generated using the KDF
described in Task A. When the decryption is over, the function stores the plaintext in an
appropriate output file.
IMPORTANT: In order to successfully decrypt the data, you have to generate the same key as
the one used in order to encrypt them. For this reason the keys must be of the same size and
derived from the same password.
Task D
[Data Signing (CMAC)]
For this task you have to implement a Cipher-based Message Authentication Code (CMAC)
generation function, using the EVP and CMAC APIs. This function reads the plaintext data from
an input file and encrypts them using the encryption function (Task B), using the key generated
by the KDF (Task A), and then generates the CMAC. After the ciphertext and the CMAC are
generated, it stores the ciphertext concatenated with the CMAC in an appropriate output file.

Task E
[Data Verification (CMAC)]
In this task you have to implement a CMAC verification function. This function reads the
ciphertext concatenated with its CMAC from an input file. Then, it separates the ciphertext from
the CMAC and decrypts the ciphertext. Using the plaintext obtained by the decryption, it
generates its CMAC and compares it to the one that came with the ciphertext. The function
returns TRUE if the CMAC is successfully verified and stores the plaintext in an appropriate file.
Otherwise, it just returns FALSE.
IMPORTANT: In order to successfully decrypt the data, you have to generate the same key as
the one used in order to encrypt them. For this reason the keys must be of the same size and
derived from the same password. The same thing applies to CMAC generation and verification.

Task F
[Using the tool]
Once you have implemented all the above functionality for your tool, use it to do the following
operations on the txt files provided:
1. Encrypt the file “encryptme_256.txt” using a 256-bit key. The key should be generated
using TUC<AM> as password. For example “TUC2020123456”. The output file should
be called “decryptme_256.txt”

2. Decrypt the file “hpy414_decryptme_128.txt” using a 128-bit key derived by the

password “hpy414”. Store the plaintext in a file named “hpy414_encryptme_128.txt”

3. Sign the file “signme_128.txt” using a 128-bit key derived from a password in the format
TUC<AM>. Store the ciphertext concatenated with its CMAC in a file named
“verifyme_128.txt”

4. Verify the files “hpy414_verifyme_256.txt” and “hpy414_verifyme_128.txt” using the

appropriate key size, as the filename specifies. The keys should be derived by the
password “hpy414”. Write in your README.txt file which of those is successfully verified,
if any.
Tool Specifications
In order to assist you in the development of this tool, we provide a basic skeleton of the tool. We
also provide some helper functions, used to print the plaintext as a string and the bytes of the
ciphertext, key and CMAC in a human readable form. The tool will receive the required
arguments from the command line upon execution as such:

Options:
-i path Path to input file
-p psswd Password for key generation
-b bits Bit mode (128 or 256 only)
-o path Path to output file
-d Decrypt input and store results to output
-e Encrypt input and store results to output
-s Encrypt+sign input and store results to output
-v Decrypt+verify input and store results to output
-h This help message

The arguments “i”, “o”, “p” and “b” are always required. Moreover one of the “d”, “e”, “s” and “v”
arguments should be provided.
Using -i and a path the user specifies the path to the input file.
Using -o and a path the user specifies the path to the output file.
Using -p and a password the user defines the string from which the AES key will be derived.
Using -b and the numbers 128 or 256 the user defines the desired key size.
Using -d the user specifies that the tool should read the ciphertext from the input file, decrypt it
and then store the plaintext to the output file.
Using -e the user specifies that the tool should read the plaintext from the input file, encrypt it
and store the ciphertext to the output file.
Using -s the user specifies that the tool should read the plaintext from the input file, encrypt it,
generate its CMAC and then store the ciphertext concatenated with its CMAC to the output file.
Using -v the user specifies that the tool should read the ciphertext concatenated with its CMAC
from the input file, decrypt it and store the plaintext to the output file only if the CMAC is
successfully verified. Otherwise, it will inform the user that the ciphertext is not verified.

Example:
./assign_1 -i plaintext.txt -o ciphertext.txt -p hpy414 -b 256 -e

The tool will generate a 256-bit key from the password “hpy414” and use this key to encrypt the
data found in “plaintext.txt” and then store the ciphertext to “ciphertext.txt”

IMPORTANT
Even if you chose to redesign your tool from scratch, and not use the provided skeleton, you
have to support the command line options described above.
Important notes

1. You need to submit all the source code of your tool, a README file, a Makefile, and all
the files you used or generated in Task F. The README file should briefly describe your
tool and contain the answer of Task F.4. You should place all these files in a folder
named <AM>_assign2 and then compress it as a .zip file. For example, if your login is
2020123456 the folder should be named 2020123456_assign2 you should commit
2020123456.zip.
2. Install the libssl-dev package using your package manager.
3. Study carefully the EVP and CMAC APIs (you can find many info online) and do ​not
bother with asymmetric encryption.
4. Do ​not​ copy-paste code from online examples, we will know ;)
5. The tool’s skeleton provided with this assignment is just an example. Feel free to define
your own functions or change the signatures of the given functions. You can even
re-design it from scratch.
6. The size of the CMAC you are going to generate is 16 bytes. Keep that in mind when
separating the CMAC from the ciphertext upon verification.
7. The ciphertext, key and CMAC are just bytes. That means that they do ​not terminate
with \0. Don’t try to print them as strings, use the provided function.
8. The ciphertext may be bigger than the plaintext due to padding. The AES block size is
16 bytes. Keep that in mind when allocating plaintext buffers.
9. Use the tab “Συζήτηση” in courses for questions.
10. Questions will be answered on Monday and Thursday.