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/[Link]/ directory, change to that
directory:
[analyst@secOps ~]$ cd ./[Link]/
[analyst@secOps [Link]]$
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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 [Link]]$ 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 [Link]]$
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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 [Link]. OpenSSL will ask for a
password and for password confirmation. Provide the password as requested and be sure to remember
the password.
[analyst@secOps [Link]]$ openssl aes-256-cbc -in
letter_to_grandma.txt -out [Link] enter aes-256-cbc
encryption password:
Verifying - enter aes-256-cbc encryption password:
[analyst@secOps [Link]]$
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 [Link]
file.
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Lab - Encrypting and Decrypting Data Using OpenSSL
[analyst@secOps [Link]]$ cat [Link]
Question:
Did the contents of the [Link] 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 [Link]]$ openssl aes-256-cbc -a -in
letter_to_grandma.txt -out [Link] 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, [Link] file:
Note: The contents of [Link] will vary.
[analyst@secOps [Link]]$ cat [Link]
U2FsdGVkX19ApWyrn8RD5zNp0RPCuMGZ98wDc26u/vmj1zyDXobGQhm/dDRZasG7
rfnth5Q8NHValEw8vipKGM66dNFyyr9/hJUzCoqhFpRHgNn+Xs5+TOtz/QCPN1bi
08LGTSzOpfkg76XDCk8uPy1hl/+Ng92sM5rgMzLXfEXtaYe5UgwOD42U/U6q73pj
a1ksQrTWsv5mtN7y6mh02Wobo3A1ooHrM7niOwK1a3YKrSp+ZhYzVTrtksWDl6Ci
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Lab - Encrypting and Decrypting Data Using OpenSSL
XMufkv+FOGn+SoEEuh7l4fk0LIPEfGsExVFB4TGdTiZQApRw74rTAZaE/dopaJn0
sJmR3+3C+dmgzZIKEHWsJ2pgLvj2Sme79J/XxwQVNpw=
[analyst@secOps [Link]]$
Questions:
Is [Link] displayed correctly now? Explain.
Yes. While [Link] 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 [Link] 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 [Link].
a. Use the command below to decrypt [Link]:
[analyst@secOps [Link]]$ openssl aes-256-cbc –a -d -in [Link]
-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 [Link] 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 [Link]]$ cat decrypted_letter.txt
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Lab - Encrypting and Decrypting Data Using OpenSSL
Questions:
Was the letter decrypted correctly?
Yes, the letter was decrypted correctly.
The command used to decrypt also contains -a option. Can you explain?
Because [Link] was Base64 encoded after the encryption process took place, [Link] must
be Base64 decoded before OpenSSL can decrypt it.
End of document
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