Anonymity • Intermediate
Tails OS Masterclass
Privacy, Security, and Anonymity from the Ground Up
3 students enrolled
3.0 hours of content
Last updated Oct 2025
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3 students
What You'll Learn
Understand the purpose, design, and limitations of Tails OS.
Safely create and verify bootable Tails USB drives from Windows, macOS, or Linux.
Run Tails securely on both physical machines and in virtual environments.
Configure Persistent Storage for encrypted data retention across sessions.
Install and manage additional software securely within the Tails environment.
Use Tor Browser and other built-in tools for anonymous browsing and communication.
Communicate safely using OnionShare, Thunderbird, and Pidgin/XMPP with OTR encryption.
Handle cryptocurrency transactions securely with Electrum inside Tails.
Protect and manage passwords, encrypted volumes (VeraCrypt, LUKS), and PGP keys.
Perform secure file deletion, hashing, and metadata removal.
Defend against cold-boot attacks, storage leaks, and other advanced threat vectors.
Apply operational security (OpSec) principles to real-world privacy and investigative workflows.
Tools & Technologies You'll Use
Tails OS (latest stable release)
Tor Browser
OnionShare (for file sharing via Tor)
Thunderbird (encrypted email)
Electrum Wallet (Bitcoin transactions within Tails)
VeraCrypt and LUKS (for encrypted storage)
GnuPG and Kleopatra (for PGP encryption)
GtkHash (file integrity and hash verification)
Metadata Anonymization Toolkit (MAT)
Pidgin/XMPP with OTR for instant messaging
Tails Persistent Storage Manager
QEMU/VirtualBox (for optional VM labs)
Instructor
Freeb00t
Founder of Dark Web Academy
OSCP | CISSP | M.S. Cybersecurity
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This course includes:
- 46 video lessons
- 2 quizzes
- Lifetime access
- Access on all devices
Course Curriculum
Introduction and Ethics
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Pre-Course Warning
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Community Introduction
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Course Introduction
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Cybersecurity Ethics and the Dark Web
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Understand Operating Systems
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Operating System Security Principles
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Pre-Course Quiz
Intro to Tails OS
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What is Tails?
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Why Use Tails?
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Pre-requisites and Prep for Tails
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Creating Tails USB from (Windows)
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Creating Tails USB from Linux
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Creating Tails USB from Mac
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Cloning Tails
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Making a Tails DVD
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Running Tails in a VM
Using Tails for the First Time
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Startup Tails on PC
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Startup Tails on Mac
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Tails First Start Steps
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Introduction to Tails Desktop
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Safely Shutting Tails Down
Tails Persistent Storage
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Tails Storage Overview
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Creating Persistent Storage
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Configuring Persistent Storage
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Using Persistent Storage
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Installing Software
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Backup and Deleting Storage
Internet and Tor on Tails OS
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Getting Online
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Tor Overview
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Sharing and Receiving Files with OnionShare
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Thundebird Overview
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Electrum Overview
Encryption and Privacy with Tails
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Password Storage
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Veracrypt and LUKS Encrypted Volumes
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Encrypting text and Files with GnuPG and Kleopatra
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Securely deleting files and diskpace
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Using GtkHash
Advanced Tails Topics
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Removing File Metadata
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Managing Boot Options
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Protecting Against Cold Boot Attacks
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Accessing LAN resources
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Secure Instant Messaging with Tails
Real World Tails
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Real-World Tails Examples
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Security Best Practices
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Troubleshooting and FAQ
Course Review
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Course Review
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Course Outro and Thanks!
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Final Quiz
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