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Uy_Charles_LAB2 - Encrypting and Decrypting Data Using OpenSSL

The document outlines a lab exercise on encrypting and decrypting data using OpenSSL, focusing on AES encryption. It details the steps for encrypting a text file and the importance of using a strong password, while also highlighting security concerns regarding the methods used. Additionally, it explains how to decrypt the encrypted file and the necessity of Base64 encoding for readability.

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Charles Uy
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© © All Rights Reserved
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4 views

Uy_Charles_LAB2 - Encrypting and Decrypting Data Using OpenSSL

The document outlines a lab exercise on encrypting and decrypting data using OpenSSL, focusing on AES encryption. It details the steps for encrypting a text file and the importance of using a strong password, while also highlighting security concerns regarding the methods used. Additionally, it explains how to decrypt the encrypted file and the necessity of Base64 encoding for readability.

Uploaded by

Charles Uy
Copyright
© © All Rights Reserved
Available Formats
Download as DOCX, PDF, TXT or read online on Scribd
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Charles A.

Uy - TW31
Lab - Encrypting and Decrypting Data Using OpenSSL
Objectives
Part 1: Encrypting Messages with OpenSSL
Part 2: Decrypting Messages with OpenSSL

Background / Scenario
OpenSSL is an open source project that provides a robust, commercial-grade, and full-featured toolkit for the
Transport Layer Security (TLS) and Secure Sockets Layer (SSL) protocols. It is also a general-purpose
cryptography library. In this lab, you will use OpenSSL to encrypt and decrypt text messages.
Note: While OpenSSL is the de facto cryptography library today, the use presented in this lab is NOT
recommended for robust protection. Below are two security problems with this lab:
1) The method described in this lab uses a weak key derivation function. The ONLY security is
introduced by a very strong password.
2) The method described in this lab does not guarantee the integrity of the text file.
This lab should be used for instructional purposes only. The methods presented here should NOT be used to
secure truly sensitive data.

Required Resources
 CyberOps Workstation Virtual Machine
 Internet access

Part 1: Encrypting Messages with OpenSSL


OpenSSL can be used as a standalone tool for encryption. While many encryption algorithms can be used,
this lab focuses on AES. To use AES to encrypt a text file directly from the command line using OpenSSL,
follow the steps below:

Step 1: Encrypting a Text File


a. Log into CyberOPS Workstation VM.
b. Open a terminal window.
c. Because the text file to be encrypted is in the /home/analyst/lab.support.files/ directory, change to that
directory:
[analyst@secOps ~]$ cd ./lab.support.files/
[analyst@secOps lab.support.files]$

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Lab – Encrypting and Decrypting Data using OpenSSL

d. Type the command below to list the contents of the encrypted letter_to_grandma.txt text file on the
screen:
[analyst@secOps lab.support.files]$ cat letter_to_grandma.txt
Hi Grandma,
I am writing this letter to thank you for the chocolate chip cookies you sent
me. I got them this morning and I have already eaten half of the box! They are
absolutely delicious!

I wish you all the best. Love,


Your cookie-eater grandchild.
[analyst@secOps lab.support.files]$

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Lab – Encrypting and Decrypting Data using OpenSSL

e. From the same terminal window, issue the command below to encrypt the text file. The command will use
AES-256 to encrypt the text file and save the encrypted version as message.enc. OpenSSL will ask for a
password and for password confirmation. Provide the password as requested and be sure to remember
the password.
[analyst@secOps lab.support.files]$ openssl aes-256-cbc -in
letter_to_grandma.txt -out message.enc
enter aes-256-cbc encryption password:
Verifying - enter aes-256-cbc encryption password:
[analyst@secOps lab.support.files]$

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Lab – Encrypting and Decrypting Data using OpenSSL

Document the password.


__cyberops___________________________________________________________________

f. When the process is finished, use the cat command again to display the contents of the message.enc
file.
[analyst@secOps lab.support.files]$ cat message.enc
Did the contents of the message.enc file display correctly? What does it look like? Explain.
No. The file seems broken as just symbols are displayed. The symbols are shown
because OpenSSL has generated a binary file.

g. To make the file readable, run the OpenSSL command again, but this time add the -a option. The -a
option tells OpenSSL to encode the encrypted message using a different encoding method of Base64
before storing the results in a file.
Note: Base64 is a group of similar binary-to-text encoding schemes used to represent binary data in an
ASCII string format.
[analyst@secOps lab.support.files]$ openssl aes-256-cbc -a -in
letter_to_grandma.txt -out message.enc
enter aes-256-cbc encryption password:

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Lab – Encrypting and Decrypting Data using OpenSSL

Verifying - enter aes-256-cbc encryption password:

h. Once again, use the cat command to display the contents of the, now re-generated, message.enc file:
Note: The contents of message.enc will vary.
[analyst@secOps lab.support.files]$ cat message.enc
U2FsdGVkX19ApWyrn8RD5zNp0RPCuMGZ98wDc26u/vmj1zyDXobGQhm/dDRZasG7
rfnth5Q8NHValEw8vipKGM66dNFyyr9/hJUzCoqhFpRHgNn+Xs5+TOtz/QCPN1bi
08LGTSzOpfkg76XDCk8uPy1hl/+Ng92sM5rgMzLXfEXtaYe5UgwOD42U/U6q73pj
a1ksQrTWsv5mtN7y6mh02Wobo3A1ooHrM7niOwK1a3YKrSp+ZhYzVTrtksWDl6Ci
XMufkv+FOGn+SoEEuh7l4fk0LIPEfGsExVFB4TGdTiZQApRw74rTAZaE/dopaJn0
sJmR3+3C+dmgzZIKEHWsJ2pgLvj2Sme79J/XxwQVNpw=
[analyst@secOps lab.support.files]$

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Lab – Encrypting and Decrypting Data using OpenSSL

Is message.enc displayed correctly now? Explain.


Yes. While message.enc is encrypted, it is now correctly displayed because it has
been converted from binary to text and encoded with Base64.

Can you think of a benefit of having message.enc Base64-encoded?


The encrypted message can now be copied and pasted in an email message, for
example.

Part 2: Decrypting Messages with OpenSSL


With a similar OpenSSL command, it is possible to decrypt message.enc.
a. Use the command below to decrypt message.enc:
[analyst@secOps lab.support.files]$ openssl aes-256-cbc –a -d -in message.enc
-out decrypted_letter.txt
b. OpenSSL will ask for the password used to encrypt the file. Enter the same password again.

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Lab – Encrypting and Decrypting Data using OpenSSL

c. When OpenSSL finishes decrypting the message.enc file, it saves the decrypted message in a text file
called decrypted_letter.txt. Use the cat display the contents of decrypted_letter.txt:
[analyst@secOps lab.support.files]$ cat decrypted_letter.txt

Was the letter decrypted correctly?


Yes, the letter was decrypted correctly.

The command used to decrypt also contains -a option. Can you explain?
Because message.enc was Base64 encoded after the encryption process took
place, message.enc must be Base64 decoded before OpenSSL can decrypt it.

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