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Analyzing and Decrypting TLS with Wireshark

In this lab, you’ll practice capturing network traffic, decrypting, and analyzing it to verify proper TLS operation. When you’re finished, you’ll know how to capture session keys and use them to decrypt traffic in Wireshark.

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Lab Info
Rating
(34)
Level
Beginner
Last updated
Aug 04, 2025
Duration
1h 0m

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Table of Contents
  1. Challenge

    Getting Started in the Lab Environment

    Here are the initial instructions and explanation of the lab environment. Read this while your environment is busy creating itself from nothing. Yes, this violates physics; we know. How fun!

  2. Challenge

    Capture an HTTPS Website and Session Keys in Wireshark Using Windows

    In this challenge ,you will be provided with a virtualized Windows desktop where you will configure it to capture session keys for all TLS sessions using the Firefox browser.

  3. Challenge

    Filter the Captured Frames and Decrypt the Capture with the Session Keys

    In this challenge, you will use information collected from the previous Challenge to filter out only the frames associated with the Globomantics website, and then apply the session keys to decrypt the messages.

  4. Challenge

    Examine the Decrypted TLS Handshake

    In this challenge, you will take a deeper look at the TLS handshake. The handshake has many detailed components, and you will examine the Client Hello, Server Hello, and Certificate messages. There is an option to use an external website to examine more details of the handshake if you like.

  5. Challenge

    Capture an HTTPS Website and Session Keys in Wireshark Using Linux Desktop, and decrypt the messages

    In this challenge, you will repeat the exercise of capturing an HTTPS website and the session keys, but this time in Linux. You will find the TCP session for the website, and then decrypt it with the session keys.

  6. Challenge

    Examine the HTTPS Session of a TLS 1.1 Server

    In this last challenge, you will use Wireshark to capture a website and examine what happens when the browser does not support the version of TLS configured on the server.

About the author

For nearly 20 years, Ross has taught and managed data networks.

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