UNIVERSITY OF INFORMATION TECHNOLOGY – VNU-HCM

FACULTY OF COMPUTER NETWORKS AND COMMUNICATIONS

1. Symmetric Cryptography

PHỤC VỤ MỤC ĐÍCH GIÁO DỤC

FOR EDUCATIONAL PURPOSE ONLY

A. OVERVIEW
1. Introduction and learning objective
Cryptography plays a vital role in modern digital communication systems. The Oxford
Dictionary1 defines cryptography as "the art of writing or solving codes" with "codes"
elsewhere defined as "a system of prearranged signals, especially used to ensure secrecy
in transmitting messages.” Historically, cryptography focused exclusively on ensuring
private communication between two parties sharing secret information in advance
using code. It was used primarily for military, government, and a few niche industry
applications for centuries.

But cryptography nowadays is much more of a science. We would say that modern
cryptography involves studying mathematical techniques for securing information,
systems, and distributed computations against adversarial attacks. Cryptography has
gone from "an art form that dealt with secret communication for the military" to "a
science to secure systems for ordinary people all across the globe". It deals with
mechanisms for ensuring integrity, techniques for exchanging secret keys, protocols for
authenticating users, electronic auctions and elections, digital currency, and more.

1
https://www.oxfordlearnersdictionaries.com
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The learning objective of this lab is for students to get familiar with the concepts in
secret-key encryption, particularly in classical cryptography and block ciphers. After
finishing the lab, students should gain first-hand experience with encryption
algorithms. Moreover, students may use crypto tools and write simple programs to
encrypt/decrypt messages. This lab will cover the following topics:
1. Classical ciphers
2. Secret-key encryption
3. Encryption modes, IV, and paddings

2. Practical environment and Prerequisites

To ensure everything goes smoothly and you achieve better results in this lab, you
are expected to be familiar with cryptography concepts and gain enough
background knowledge about symmetric cryptography. Besides, programming skill
(with your preferred language, e.g., Python, C/C++, Golang) is also necessary.

This lab requires you have the following preparations:

1. A Linux-based computer (using Ubuntu or CentOS operating system) that

preinstalled OpenSSL for encryption and decryption.
2. An IDE of your preferred programming language.

3. Backgrounds and Prerequisites

The following section summarizes some of the key aspects to help you review the
knowledge that you may already have obtained before getting started. You can also
read the textbooks and related references that I listed in section 1.4 for more details.

Concepts
Before beginning, we define some terms. When we’re encrypting a message,
§ The plaintext (p) refers to the original or unencrypted message
§ The ciphertext (C) refers to the coded or encrypted message.
A cipher is therefore composed of two functions:
§ Encryption or Enciphering (E) turns plaintext into ciphertext.
§ Decryption or Deciphering (D) turns a ciphertext back into plaintext.
Written as functions:
C=E(Ke,p)
p=D(Kd,C)

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where Ke and Kd are encryption and decryption keys, respectively.

Figure 1: Basic encryption and decryption

Techniques used for deciphering a message without any knowledge of the

enciphering details fall into the area of cryptanalysis (breaking the code). The areas
of cryptography and cryptanalysis together are called cryptology.

Taxonomy

Concerning encryption methodologies, there are two types of ciphers:

1. Symmetric ciphers (or Secret-key ciphers): Using a single key for encryption and
decryption. It was the only type of encryption in use before the development
of public-key encryption in the 1970s (Figure 2).

Figure 2: Symmetric Encryption model

2. Asymmetric ciphers (or Public-key ciphers): Use two related keys, a public key
and a private key, to perform complementary operations, such as encryption
and decryption or signature generation and signature verification.

The two basic building blocks of all encryption techniques are substitution and
transposition (Figure 3)

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Figure 3: Substitution and Transposition example

Block cipher

A block cipher is one in which a block of plaintext is treated as a whole and used to
produce a ciphertext block of equal length (Figure 4). Typically, a block size of 64 or
128 bits is used. As with stream cipher, the two users share a symmetric encryption
key. Using some of the modes of operation, a block cipher can be used to achieve
the same effect as a stream cipher.

Figure 4: Block cipher

The Advanced Encryption Standard (AES) algorithms

AES (Advanced Encryption Standard) is a symmetric block cipher that is intended to

replace DES (Data Encryption Standard) as the approved standard for a wide range of
applications. It was published by the National Institute of Standard and Technology
(NIST) in 2001.

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Figure 5 shows the overall structure of
the AES encryption process. The cipher
takes a plaintext block size of 128 bits or
16 bytes. The key length can be 16, 24,
or 32 bytes (128, 192, or 256 bits). The
algorithm is referred to as AES-128,
AES-192, or AES-256, depending on the
key length.

The input to the encryption and

decryption algorithms is a single 128-
bit block. The cipher consists of N
rounds, where the number of rounds
depends on the key length: 10 round
for a 16-byte key, 12 rounds for a 24-
byte key, and 14 rounds for a 32-byte
key.

Figure 5: AES Encryption Process

Figure 6: AES parameters

The modes of operation of block cipher

Block cipher is a deterministic algorithm operating on fixed-length groups of b bits,

called blocks. If the amount of plaintext to encrypt is greater than b bits, then the
block cipher can still be used by breaking the plaintext up into b-bit blocks. When
multiple blocks of plaintext are encrypted using the same key, several security issues
arise.

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Modes of operation is a technique for enhancing the effect of a cryptographic
algorithm or adapting the algorithm for an application, such as applying a block
cipher to a sequence of data blocks or a data stream. The five modes are intended
to cover a wide variety of applications of encryption for which a block cipher could
be used. To apply a block cipher in a variety of applications, five modes of
operation have been defined by NIST (SP 800-38A):

1. ECB – Electronic Codebook

2. CBC – Cipher Block Chaining
3. CFB – Cipher Feedback
4. OFB – Output Feedback
5. CTR - Counter

Figure 7: Block Cipher Modes of Operation

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B. LAB TASKS
1. Kickoff: Crack the code
Let’s begin with a straightforward task that does not use any cipher algorithm.
Try to solve the following codes:
a. We need to find the code to open the lock in Figure 8. The lock has a three-
digit pin that satisfies five conditions (hints). Can you crack this code? If
it’s possible, explain how.

b. Find the corresponding encoding for the numbers 1 to 9 according to the

clues provided in Table 1:
§ Each symbol in the set (µµµµµµµµµ) unique encoding for one of
the numbers from 1 to 9.
§ The rightmost column is the sum of the numbers in each row.
§ The bottom row is the sum of the number in each column.
§ Each symbol “?” can represent either a one-digit number or a two-digit
number. Thay can be different from each other.

Figure 8: Crack the code to open the lock

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µ µ µ µ ?
µ µ µ µ µµ
? ? µ µ µµ
? µ µ µ µµ
µµ µµ µµ µµ
Table 1: Find the corresponding encoding for each number

2. Caesar cipher
In this task, you must write an application using your chosen programming
language (without any cryptography libraries) to encrypt and decrypt a message
using Caesar cipher. Your application should satisfy the following requirements:
§ Allow user can encrypt or decrypt message (with the given key)
§ Allow brute-force all possible keys k to find the plaintext of given
ciphertext without its key.
Test your program with a message of at least 100 words and compare the result
with other cryptography tools (like Cryptool 2) to verify. Then use your program
to crack the following ciphertext:

Gurer ner gjb xvaqf bs crbcyr va guvf jbeyq: gubfr jub ner ybbxvat
sbe n ernfba naq gubfr jub ner svaqvat fhpprff. Gubfr jub ner
ybbxvat sbe n ernfba nyjnlf frrxvat gur ernfbaf jul gur jbex vf
abg svavfurq. Naq crbcyr jub svaq fhpprff ner nyjnlf ybbxvat sbe
ernfbaf jul gur jbex pna or pbzcyrgrq.

Do you find any special concerning the key used to encrypt this ciphertext?

Tips: Using the Caesar algorithm

Encryption : C = E(k, p) = (p + k) mod 26

Decryption : p = D(k,C) = (C- k) mod 26

where C = Ciphertext, p = plaintext, k is key

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3. Mono-alphabetic substitution cipher and frequency analysis
(This task is based on a lab in SEED Labs materials by Wenliang Du, Syracuse University.)

It is well-known that monoalphabetic substitution cipher (also known as the

monoalphabetic cipher) is not secure because it can be subjected to frequency
analysis. You are given a ciphertext encrypted using a monoalphabetic cipher in this
lab. Each letter in the original text is replaced by another letter, where the
replacement does not vary (i.e., a letter is always replaced by the same letter during
the encryption.

You need to find out the original text of the given ciphertext (Mono-alphabetic
ciphertext.txt) using the frequency analysis technique. It is known that the
original text is an English article. Describe how to find the plaintext in detail
(step-by-step).

Please note that you are not allowed to use the automatic mode of any tools (like CrypTool,
dCode, quipqiup,…) to decrypt.

Tips: Using the frequency analysis, you can easily find the plaintext for some of the
characters. For those characters, you may want to change them back to their plaintext, as you
may be able to get more clues. It’s better to use capital letters for plaintext, so for the same
letter, we know which is plaintext and which is ciphertext.

If you use Linux or macOS, you can use the tr command. For example, in the following, we
replace letters a, e and t in in.txt with letters X, G, E, respectively; the results are saved in
out.txt.
$ tr ‘aet’ ‘XGE’ < in.txt > out.txt
You can also use Cryptool or dCode to decrypt it manually by analyzing and replacing letters.
There are many online resources that you can use. Two valuable links as the following:

§ Cryptool Online N-gram analysis: This website can produce the statistics from
sequence), trigram frequencies (3-letter sequence), etc.

§ http://norvig.com/mayzner.html: This web page provides frequencies for a typical

English plaintext, including unigram, bigram, and trigram frequency.

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4. Familiar with the block cipher
We can use the openssl enc command to encrypt / decrypt a file. To see the
manual, you can type man openssl and man enc.

$ openssl enc -ciphertype -e -in plain.txt -out cipher.bin \

-K 00112233445566778889aabbccddeeff \
-iv 0102030405060708
Please replace the ciphertype with a specific cipher type, such as -aes-128-cbc,
-bf-cbc, etc. You can find the meaning of the command-line options and all the
supported cipher types by typing “man enc”. We include some common options
for the openssl enc command in the following:

-in <file> input file

-out <file> output file
-e encrypt
-d decrypt
-K/-iv key/iv in hex is the next argument
-[pP] print the iv/key (then exit if -P)

5. Encryption Mode – ECB vs. CBC

(This task is based on a lab in SEED Labs materials by Wenliang Du, Syracuse University.)

The file pic_original.bmp that include in this lab is a simple picture. We would like
to encrypt this picture, so people without the encryption keys cannot know what
is in the picture. Please encrypt the file using the ECB (Electronic Code Book) and
CBC (Cipher Block Chaining) modes, and then do the following:
1. Let us treat the encrypted picture as a picture and use picture viewing
software to display it. However, For the .bmp file, the first 54 bytes contain
the header information about the picture, we have to set it correctly, so the
encrypted file can be treated as a legitimate .bmp file. We will replace the
header of the encrypted picture with that of the original picture. We can use
the bless hex editor tool (already installed on our VM) to directly modify
binary files. We can also use the following commands to get the header from
p1.bmp, the data from p2.bmp (from offset 55 to the end of the file), and
then combine the header and data together into a new file.

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2. Display the encrypted picture using a picture viewing program. Can you
derive any useful information about the original picture from the
encrypted picture? Please explain your observations.
3. Select a picture of your choice, repeat the experiment above, and report
your observations.

$ head -c 54 pic_original.bmp > header

$ tail -c +55 p1.bmp > body1
$ tail -c +55 p2.bmp > body2
$ cat header body1 > file1.bmp
$ cat header body2 > file2.bmp

6. Padding - optional
(This task is based on a lab in SEED Labs materials by Wenliang Du, Syracuse University.)

For block cipher, when the size of plaintext is not a multiple of the block size,
padding may be required. The PKCS#5 padding scheme is widely used by many
block ciphers

We will conduct the following experiments to understand how this type of

padding works:

1. Use ECB, CBC, CFB, and OFB modes to encrypt a file (you can pick any
cipher). Please report which modes have paddings and which ones do not.
For those that do not need paddings, please explain why.

2. Practice about block cipher padding

Phase 1: Let’s create three files, which contain 5 bytes, 10 bytes, and 16 bytes,
respectively. Please note that at least one of these files must included your
student’s id and all of them may be text or binary files.
Phase 2 - Encyption: Use openssl enc -aes-128-cbc -e to encrypt these
files using 128-bit AES with CBC mode. Please describe the size of the
encrypted files.
Phase 3 - Decryption: We would like to see what is added to the padding
during the encryption. To achieve this goal, we will decrypt these files using
openssl enc -aes-128-cbc -d. Unfortunately, decryption will

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automaticaly remove the padding by default, making it imposible for us to
see the padding. However, the command does have an option called
-nopad, which disables the padding, i.e., during the decryption, the
command will not remove the padded data. Therefore, by looking at the
decrypted data, we can see what data are used in the padding. Please use
this technique to figure out what paddings are added to these files.

It should be noted that padding data may not be printable, so you need to use a hex
tool to display the content. The following example shows how to display a file in hex
format.

C. REQUIREMENTS
You are expected to complete all tasks in section B (Lab tasks). Advanced tasks
are optional, and you could get bonus points for completing those tasks. We
prefer you work in a team of two or three to get the highest efficiency.

Your submission must meet the following requirements:

§ You need to submit a detailed lab report in .docx (Word Document) format,
using the report template provided on the UIT Courses website.

§ The report in either Vietnamese or English is accepted, that’s up to you.

The report written in the mixing of multiple languages is not allowed
(except for the untranslatable keywords).

§ When it comes to programming tasks (require you to write an application or

script), please attach all source-code and executable files (if any) in your
submission. Please also list the important code snippets followed by
explanations and screenshots when running your application in your
report. Simply attaching code without any explanation will not receive
points.

§ Submit work you are proud of – don’t be sloppy and lazy!

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Your submissions must be your own. You are free to discuss with other
classmates to find the solution. However, copying reports is prohibited,
even if only a part of your report. Both reports of the owner and the copier
will be rejected. Please remember to cite any source of the material
(website, book,…) that influences your solution.

Notice: Combine your lab report and all related files into a single ZIP file (.zip),
name it as follow:

StudentID1_StudentID2_ReportLabX.zip

D. REFERENCES
[1] William Stallings, Cryptography and network security: Principles and practice, 7th ed,
Pearson Education, 2017. Chapter 3, chapter 4, chapter 6, chapter 7

[2] Wenliang Du (Syracuse University), SEED Cryptography Labs

https://seedsecuritylabs.org/Labs_20.04/Crypto/

[3] Wenliang Du (Syracuse University), SEED Cryptography Labs

https://seedsecuritylabs.org/Labs_20.04/Files/Crypto_Encryption

Training platforms and related materials

§ ASecuritySite-https://asecuritysite.com

§ Cryptopals-https://cryptopals.com

Attention: Don’t share any materials (slides, readings, assignments, labs, etc..) out of our
class without my permission!

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