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

Instructions

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]$

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,

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Lab - Encrypting and Decrypting Data Using OpenSSL

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]$

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]$

Question:

Document the password.

Type your answers here.
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

Question:

Did the contents of the message.enc file display correctly? What does it look like? Explain.
- Yes, the content of the message.enc file is displayed correctly, but it looks like a random string of
characters that cannot be read. This shows that the file has been successfully encrypted, changing
the original text into a format that no one can understand without the password to decrypt it. The
purpose of this is to protect sensitive information from people who do not have access
Type your answers here.

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.

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Lab - Encrypting and Decrypting Data Using OpenSSL

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:
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]$

Questions:

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
Type your answers here.

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
Type your answers here.

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:

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Lab - Encrypting and Decrypting Data Using OpenSSL

[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.
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

Questions:

Was the letter decrypted correctly?

- Yes, the letter was decrypted correctly
Type your answers here.

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
Type your answers here.

End of document

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