Packet Tracer - Explore File and Data Encryption

Objectives
Part 1: Discover the FTP Account Credentials for Mary
Part 2: Upload Confidential Data using FTP
Part 3: Discover the FTP Account Credentials for Bob
Part 4: Download Confidential Data using FTP
Part 5: Decrypt the Contents of a Sensitive File

Background
In this Packet Tracer activity, you will access the encrypted content of multiple files and transfer a file to an
FTP server. Then, in the role of another user, you will download the file from the FTP server and decrypt the
file contents. The IP addressing, network configuration, and service configurations are already complete. You
will use the client devices to transfer a file with encrypted data to another device.
To decrypt text and files in this activity, you will use OpenSSL. 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.
Note: While OpenSSL is the de facto cryptography library today, the use presented in this activity is NOT
recommended for robust protection. Below are two security problems with this activity:
o The method described in this activity uses a weak key derivation function. The ONLY security is
introduced by a very strong password.
o The method described in this activity does not guarantee the integrity of the text file.
This activity should be used as a learning tool only. The methods presented here should NOT be used to
secure truly sensitive data.

Resources
The CSE-LABVM installed in VirtualBox
Note: It is recommended that you use the CSE-LABVM for the decryption tasks in this activity. The CSE-
LABVM was installed during the Lab - Install a Virtual Machine on a Personal Computer.

Instructions

Part 1: Discover the FTP Account Credentials for Mary

Mary's laptop is named Laptop BR-1 in the Branch Office. Mary has a text document on her laptop that
contains her FTP login information in encrypted form. The contents must be decrypted to enable access to
the BR Server which is located in the Branch Wiring Closet.

Step 1: Access the text document on Mary's Laptop.

a. Click Laptop BR-1 > Desktop tab > Text Editor.
b. In the Text Editor window, click File > Open.
c. Click the document maryftplogin.txt and click OK.

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Packet Tracer – Exploring File and Data Encryption

Step 2: Decrypt Mary’s FTP account information.

a. Highlight all the text from the maryftplogin.txt file and copy it.
b. Start the CSE-LABVM.
c. Double click the Terminal icon on the desktop to open a terminal.
d. Use the following command to decrypt the contents of the file and reveal the FTP login information for
Mary.
cisco@labvm:~$ echo
'U2FsdGVkX1+sKwL7uceALGKqAQ78WWown3ok73zicO8GLYu2SpMvLEwCB7HsyRC3MeimUjiXRCLw
OSSahAraUrnEtkClGK4tytP9hludc6k=' | openssl aes-256-cbc -pbkdf2 -a -d
This command sends the encrypted text to the OpenSSL application. The aes-256-cbc option tells
OpenSSL to use the Advanced Encryption System with a 256 bit key length and Cipher Block Chaining.
The pbkdf2 option enables Password-Based Key Derivation Function 2 which applies a hash-based
message authentication code or HMAC to the password along with salt. The -a option tells OpenSSL to
encode the encrypted message using a different encoding method of Base64. The -d option tells the
application to decrypt the data.
e. When you are asked for the decryption password, use maryftp123.
enter aes-256-cbc decryption password: maryftp123
Question:

What is the username and password for Mary’s FTP account?

Type your answers here.

Part 2: Upload Confidential Data using FTP

Mary works for a credit card agency and needs to send the agency a file that contains the data of some
customers. In Part 2, you will verify that the data is encrypted before uploading it to the BR Server.

Step 1: View the confidential document on Laptop BR-1

a. Return to Laptop BR-1. Open the Text Editor, if necessary, and click File > Open.
b. Click the document clientinfo.enc and click OK.
Question:

What form is the data in?

Type your answers here.

Step 2: Connect to the BR Server.

a. Close the Text Editor window, and then click Command Prompt.
b. At the prompt, enter the ftp 10.0.3.30 command to connect to the BR Server.
c. Use Mary's credentials that you decrypted early to authenticate.

Step 3: Upload a file to the FTP server.

a. At the ftp> prompt, enter the command dir to view the current files stored on the server.
b. Use the put command to upload the clientinfo.enc file to the server.
c. At the ftp> prompt, enter the command dir and verify the clientinfo.enc file is now on the server.
d. Enter quit to end the FTP session.
Question:

If threat actors were to capture the file transfer, what would be in clear text?
Type your answers here.

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Packet Tracer – Exploring File and Data Encryption

Part 3: Discover the FTP Account Credentials for Bob

Bob needs to access the contents of the file Mary stored on the BR Server to verify some customer
information. Like Mary, Bob needs to decrypt his FTP login information in order to access the BR Server and
download the file.

Step 1: Access the text document on Bob's Laptop.

a. In Branch Office, click Laptop BR-2, and then open the Text Editor.
b. In the Text Editor window, click File > Open.
c. Click the document bobftplogin.txt and click OK.

Step 2: Decrypt Bob’s FTP account information.

a. Highlight all the text from the bobftplogin.txt file and copy it.
b. Return to the terminal window in the CSE-LABVM.
c. Use the following command to decrypt the contents of the file and reveal the FTP login information for
Bob.
cisco@labvm:~$ echo
'U2FsdGVkX1/+3jGTemCqs3e4dK8+b0xfXJiq4eoU0lQgRV9aZQPqJCBsYJWc9lDQwiB2svhiWSUV
hCRS5qBrjgmDZF3q/dXqaCrZRR5prjE=' | openssl aes-256-cbc -pbkdf2 -a -d
d. When you are asked for the decryption password, use bobftp123.
enter aes-256-cbc decryption password: bobftp123
Question:

What is the username and password for Bob’s FTP account?

Type your answers here.

Part 4: Download Confidential Data using FTP

In this Part, you will download and decrypt the confidential data stored on the BR Server.

Step 1: Connect to the BR Server.

a. In Branch Office on Laptop BR-2, close the Text Editor window, and then click Command Prompt.
b. At the prompt, enter the ftp 10.0.3.30 command to connect to the BR Server.
c. Use Bob's credentials that you decrypted early to authenticate.

Step 2: Download the file to Bob’s PC.

a. At the ftp> prompt, enter the command dir to view the current files stored on the BR Server.
b. Use the get command to download the clientinfo.enc file from the server.
c. Enter quit to end the FTP session.
d. At the C:\> prompt, enter the command dir and verify the clientinfo.enc file is now on Laptop BR-2.
Question:

If threat actors were to capture the file transfer crossing the internet, what would be in clear text?
Type your answers here.

Part 5: Decrypt the Contents of a Sensitive File

In this Part, you will decrypt the clientinfo.enc file.

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Packet Tracer – Exploring File and Data Encryption

Step 1: Get the decryption key.

Now that Bob has the file, he needs to decrypt it so that he can read it. Earlier, Mary sent Bob an email with
the decryption key for the file. Use the email program to retrieve the encryption key for the clientinfo.enc file.
a. Close the Command Prompt window, and then click Email.
b. Click the Email with the subject Decryption Key and record the decryption key below.
Question:

What is the decryption key to access the confidential information in the clientinfo.enc file?
Type your answers here.

Step 2: Decrypt the contents of the clientinfo.enc file.

a. Close the Email window, and the click Text Editor.
b. In the Text Editor window, click File > Open, click the document clientinfo.enc, and then click OK.
c. Highlight all the text in the clientinfo.enc file and copy it.
d. In the CSE-LABVM, click the Menu button and click Text Editor Pluma.
e. Click Edit > Paste, and then click File > Save.
f. Save the file with the name clientinfo.enc.
g. Close Pluma.
h. In the terminal, enter the ls command to verify that clientinfo.enc is in the current directory. If not,
navigate to the directory where clientinfo.enc is stored.
i. Use the following command to decrypt the clientinfo.enc file.
cisco@labvm:~$ openssl aes-256-cbc -pbkdf2 -a -d -in clientinfo.enc -out
clientinfo.txt
j. When prompted for the decryption password, use the password you discovered in the email from Mary.
enter aes-256-cbc decryption password:
cisco@labvm:~$
k. Enter the ls command to see that a new file, clientinfo.txt, has been added to the directory.
l. Use any method you wish to open the clientinfo.txt file to see the decrypted contents.
Question:

What is the first name listed in the clientinfo.txt file?

Type your answers here.

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Packet Tracer – Exploring File and Data Encryption

Answer Key

Part 1: Discover the FTP Account Credentials for Mary

Step 1: Access the text document on Mary's Laptop.

Step 2: Decrypt Mary’s FTP account information.

What is the username and password for Mary’s FTP account?
username: mary password: cisco321

Part 2: Upload Confidential Data using FTP

Step 1: View the confidential document on Laptop BR-1

What form is the data in?
Encrypted form

Step 2: Connect to the BR Server.

Step 3: Upload a file to the FTP server.

If threat actors were to capture the file transfer, what would be in clear text?
The username: mary password: cisco321 for the FTP connection are in clear text but the contents of
the document are encrypted.

Part 3: Discover the FTP Account Credentials for Bob

Step 1: Access the text document on Bob's Laptop.

Step 2: Decrypt Bob’s FTP account information.

What is the username and password for Bob’s FTP account?
username: bob password: ninja123

Part 4: Download Confidential Data using FTP

Step 1: Connect to the BR Server.

Step 2: Download the file to Bob’s PC.

If threat actors were to capture the file transfer crossing the internet, what would be in clear text?
The username: bob password: ninja123 for the FTP connection are in clear text but the contents of
the document are encrypted.

Part 5: Decrypt the Contents of a Sensitive File

Step 1: Get the decryption key.

What is the decryption key to access the confidential information in the clientinfo.enc file?
cisco123

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Packet Tracer – Exploring File and Data Encryption

Step 2: Decrypt the contents of the clientinfo.enc file.

What is the first name listed in the clientinfo.txt file?
Drew N. Stark
End of document

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