Tails Linux Mastery Guide
A Complete One-Day Journey to Anonymous and Secure Computing
Download/Print Version: Day 2: Tails Linux Mastery Guide PDF
Introduction: Why Tails?
Tails (The Amnesic Incognito Live System) represents a completely different philosophy than Puppy Linux. While Puppy optimizes for speed and efficiency, Tails optimizes for privacy, anonymity, and security above all else.
What Makes Tails Unique:
- Forces all internet traffic through Tor network
- Leaves no trace on the computer you use it on
- Uses state-of-the-art cryptographic tools
- Amnesia by default (forgets everything on shutdown)
- Designed for activists, journalists, and privacy-conscious users
- Endorsed by Edward Snowden and privacy advocates worldwide
Today’s Learning Goals:
- Understand the Tor network and how it protects you
- Master anonymous browsing and communication
- Learn encryption fundamentals (files, messages, email)
- Configure persistent storage securely
- Recognize surveillance and tracking techniques
- Use Tails for real-world privacy scenarios
- Understand the threat models Tails protects against
Time Required: 6-8 hours (with breaks)
Critical Context: Tails isn’t just a tool—it’s a complete security environment. Every feature serves a privacy purpose. Today, you’ll learn not just how to use Tails, but why each feature matters and when you need them.
Morning Session (8:00 AM - 12:00 PM)
Hour 1: Understanding Threat Models and Privacy (8:00 - 9:00 AM)
Before using Tails, you must understand what it protects against—and what it doesn’t.
What is a Threat Model?
Definition: A threat model identifies:
- Who might want to surveil you (adversaries)
- What they want to learn (information at risk)
- How they might attack you (attack vectors)
- What you’re protecting (assets)
Exercise 1: Personal Threat Assessment (20 minutes)
Before booting Tails, think through these scenarios:
Scenario A: Casual Privacy
- Adversary: Advertisers, data brokers, tech companies
- Goal: Build profile for targeted ads, sell your data
- Methods: Cookies, trackers, browser fingerprinting
- Protection needed: Moderate (Tor Browser, tracker blocking)
Scenario B: Investigative Journalism
- Adversary: Government agencies, corporations being investigated
- Goal: Identify sources, prevent publication
- Methods: Network surveillance, device seizure, legal pressure
- Protection needed: High (Tails, encryption, OpSec discipline)
Scenario C: Activist Organizing
- Adversary: Authoritarian governments, opposition groups
- Goal: Identify organizers, disrupt movement
- Methods: Mass surveillance, metadata analysis, informants
- Protection needed: Very high (Tails, air-gapped systems, physical security)
Scenario D: Whistleblowing
- Adversary: Resourced organizations with legal power
- Goal: Identify whistleblower, prosecute, discredit
- Methods: All available surveillance, forensics, legal discovery
- Protection needed: Maximum (Tails, physical anonymity, opsec perfection)
Write down:
- Which scenario closest matches why you’re learning Tails?
- What information do you want to protect?
- Who might want that information?
- What could they do with it?
Understanding Tails’ Protection Scope:
Tails DOES protect against:
- ✓ Network surveillance of your internet traffic
- ✓ Website tracking and profiling
- ✓ Digital traces on the computer you’re using
- ✓ Routine traffic analysis
- ✓ Commercial tracking and data collection
- ✓ Most government mass surveillance programs
Tails DOES NOT protect against:
- ✗ Targeted attacks against you specifically
- ✗ Physical surveillance (cameras, keyloggers)
- ✗ Compromised hardware (pre-installed malware)
- ✗ Your own mistakes (revealing identity in messages)
- ✗ Correlation attacks (advanced traffic analysis)
- ✗ Legal compulsion to reveal identity
- ✗ Physical device seizure after use
The Critical Understanding: Tails is a tool, not magic. It provides technical protection, but you must provide operational security (OpSec). Your behavior matters as much as the technology.
How Tails Achieves Anonymity
The Tor Network:
You → Entry Guard → Middle Relay → Exit Relay → Website
(encrypted) (encrypted) (decrypted) (sees exit IP)
Key Principles:
- Encryption Layers: Your traffic is encrypted three times
- Like an onion (hence “The Onion Router”)
- Each relay only sees previous and next relay
- No single point knows both source and destination
- Random Path: Each connection takes different route
- Makes pattern analysis extremely difficult
- Protects against single compromised relay
- Exit Node Anonymity: Website sees exit node, not you
- Your IP address is hidden
- Your location is hidden
- But: Exit node can see unencrypted traffic (use HTTPS!)
Exercise 2: Tor Visualization (15 minutes)
Draw or diagram:
- Your normal internet connection path
You → ISP → Website- ISP sees: Your IP, destination, timing
- Website sees: Your IP, location, identity
- Your Tor connection path
You → Entry → Middle → Exit → Website- Entry sees: Your IP (but not destination)
- Middle sees: Only relay IPs
- Exit sees: Destination (but not your IP)
- Website sees: Only exit node IP
Why This Matters: Understanding Tor’s architecture helps you understand its limitations. Tor protects the path, but you must protect the endpoints (your behavior).
Amnesia: The Live System Concept
What “Amnesic” Means:
Every time you shut down Tails:
- RAM is wiped (contains all your session data)
- No trace remains on the host computer
- Next boot is fresh (like it never happened)
Why This Matters:
Traditional operating systems leave evidence:
- Browser history (even “private mode”)
- File system artifacts
- Registry entries (Windows)
- Temporary files
- Swap file data
- Thumbnail caches
Tails leaves none of this because:
- Runs entirely in RAM
- Never writes to host system drive
- Secure deletion of sensitive data
- RAM is volatile (loses data when powered off)
The Trade-Off: Amnesia means nothing persists unless you explicitly configure it. This is intentional—default to forgetting everything is safest.
Hour 2: First Boot and Initial Configuration (9:00 - 10:00 AM)
Booting Tails
- Select Tails from Ventoy menu
- Tails Boot Menu appears:
- “Tails” - Normal boot
- “Tails (Troubleshooting Mode)” - If normal boot fails
- “Tails (External Hard Disk)” - For some hardware
- Choose “Tails” and press Enter
What’s Happening:
- Tails is loading into RAM
- Checking hardware compatibility
- Initializing security features
- This takes longer than Puppy (2-5 minutes normal)
Welcome Screen
The Welcome to Tails Screen appears with critical options:
Language and Region:
- Select your language
- Choose keyboard layout
- Privacy consideration: Use English if possible (less fingerprintable)
Additional Settings (click + icon):
- Administration Password:
- What it is: Sudo password for this session
- When needed: Installing software, system changes
- Set it: Check “Enable” and create strong password
- Security note: Only exists for this session
- MAC Address Anonymization:
- What it is: Changes your network card’s ID
- Why: MAC addresses are unique and trackable
- Recommendation: Leave enabled (default)
- When to disable: Some networks block MAC spoofing
- Offline Mode:
- What it is: Start without network connection
- When to use: Working with sensitive files locally
- Why: Prevents accidental network exposure
- Unsafe Browser:
- What it is: Firefox without Tor (direct internet)
- When to use: Captive portals (hotel/airport WiFi login)
- Why provided: Some networks require login before Tor works
- Danger: Reveals your real IP—use only when necessary
Exercise 3: Secure Initial Configuration (15 minutes)
Your first boot checklist:
- Language: English (most anonymous)
- Keyboard: Your actual layout (usability matters)
- Administration Password: ✓ Enable with strong password
- MAC Anonymization: ✓ Keep enabled
- Offline Mode: ✗ Leave disabled (we need network today)
- Unsafe Browser: ✗ Leave disabled (we don’t need it now)
Click “Start Tails”
Wait for desktop to load:
- Background connects to Tor network
- System initializes security features
- This takes 1-3 minutes after desktop appears
Tor Connection Notification:
- Watch for “Connected to Tor successfully”
- Green onion icon in system tray = Connected
- Until this appears, no internet access
Understanding the Tails Desktop
Desktop Environment: GNOME
- More polished than Puppy’s lightweight interface
- Organized “Activities” menu (top-left)
- System status indicators (top-right)
- Application dock (left side, appears on hover)
Critical Desktop Elements:
Top Bar:
- Activities (left): Access all applications
- Date/Time (center): Current UTC or local time
- System Icons (right):
- Onion icon (Tor status)
- Network icon
- Sound icon
- Power menu
Important Applications:
Activities → show all applications:
- Tor Browser: Your gateway to anonymous internet
- Thunderbird: Email client with OpenPGP support
- KeePassXC: Password manager
- OnionShare: Anonymous file sharing
- MAT2: Metadata removal tool
- Electrum: Bitcoin wallet
- Files: File manager
Notice What’s Missing:
- No standard Firefox (only Tor Browser)
- No Chrome, Edge, or other browsers
- Limited application selection (intentional)
- Only privacy-preserving tools included
Why This Matters: Every application in Tails is chosen for security. Random software installation could compromise anonymity. This curated approach is a feature, not a limitation.
Exercise 4: Desktop Familiarization (15 minutes)
- Explore Activities menu:
- Click “Activities”
- Browse available applications
- Notice security-focused selections
- Check Tor Connection:
- Click onion icon (top-right)
- Read Tor circuit information
- Understand: Entry, Middle, Exit relays
- Open Files (file manager):
- Notice: Limited directory structure
- Home folder is empty (clean slate)
- Amnesia sidebar (persistent storage not yet configured)
- System Settings:
- Activities → Settings
- Browse available options
- Notice: Some settings are locked/simplified (security)
Hour 3: Anonymous Browsing with Tor Browser (10:00 - 11:00 AM)
Tor Browser Fundamentals
What Makes Tor Browser Different:
- Routes traffic through Tor network
- Resists fingerprinting (makes you look like everyone else)
- Blocks trackers and cookies by default
- Disables JavaScript on high security
- Isolates tabs and websites
- Clears everything on close
Launch Tor Browser:
- Activities → Tor Browser
- Or click “Tor Browser” icon in dock
- Wait for connection (usually immediate if Tor already connected)
First Launch:
- “Tor Browser is ready”
- Notice: DuckDuckGo is default search engine (privacy-respecting)
- URL bar shows .onion availability when applicable
Tor Browser Security Slider
Critical Feature: Security Level
- Access Security Settings:
- Click shield icon (address bar, right side)
- Or menu (≡) → Settings → Privacy & Security → Security Level
-
Three Security Levels:
Standard (Default):
- All Tor Browser features enabled
- JavaScript enabled on all sites
- Best compatibility with websites
- Use for: Normal browsing, trusted sites
Safer:
- JavaScript disabled on non-HTTPS sites
- Some fonts and symbols disabled
- Some website features may break
- Use for: General anonymous browsing
Safest:
- JavaScript disabled on ALL sites
- Images disabled by default
- Many website features disabled
- Use for: Maximum anonymity, high-risk scenarios
Exercise 5: Security Level Testing (20 minutes)
Test each security level to understand trade-offs:
Part A: Standard Security
- Set security to “Standard”
- Visit: https://www.nytimes.com
- Page loads fully
- JavaScript works
- Videos play
- Interactive features work
- Visit: https://check.torproject.org
- Confirms you’re using Tor
- Shows your exit node IP
- Important: This is NOT your real IP!
- Search for something (use DuckDuckGo)
- Notice: No personalized results
- No location-based results
- Clean, untracked searching
Part B: Safer Security
- Change to “Safer” mode
- Reload nytimes.com
- Some features broken?
- Most content still accessible
- Faster loading (less JavaScript)
- Visit: http://example.com (note: HTTP, not HTTPS)
- JavaScript disabled on this site
- Basic HTML still works
Part C: Safest Security
- Change to “Safest” mode
- Reload any website
- Very minimal functionality
- No JavaScript at all
- Text and links only
- Feels like web from 1990s
- Try searching
- Still works! DuckDuckGo works without JavaScript
- Results load (no fancy features)
Understanding the Trade-Off:
- More security = Less convenience
- More functionality = More fingerprintable
- Choose based on your threat model
Recommendation for Today: Use “Safer” mode as default. Switch to “Safest” for sensitive research. Only use “Standard” if you trust the website.
Anonymous Browsing Best Practices
DO:
- ✓ Use HTTPS websites whenever possible
- ✓ Use DuckDuckGo or Startpage for searches
- ✓ Stay logged out of personal accounts
- ✓ Assume websites can see each other (don’t link identities)
- ✓ Use Security Slider appropriately
- ✓ Check that Tor is connected (green onion)
- ✓ Close browser between sensitive activities
DON’T:
- ✗ Log into personal accounts (Gmail, Facebook, etc.)
- ✗ Download files unnecessarily
- ✗ Install browser extensions
- ✗ Maximize browser window (fingerprinting risk)
- ✗ Enable Flash, Java, or similar plugins
- ✗ Torrent files through Tor
- ✗ Use Tor and VPN simultaneously (usually counterproductive)
Exercise 6: Fingerprinting Awareness (20 minutes)
Browser Fingerprinting is how websites identify you without cookies.
Test Your Fingerprint:
- Visit: https://coveryourtracks.eff.org
- (Previously called Panopticlick)
- Click “Test your browser”
- Wait for analysis
- Results Explanation:
- Unique fingerprint? Hopefully “No” in Tails!
- Tracking cookies? Should be blocked
- Fingerprinting protection? Should be “Yes”
- Compare with normal browser (mental exercise):
- Normal browser: Unique fingerprint from screen size, fonts, plugins, etc.
- Tor Browser in Tails: Same fingerprint as thousands of other Tails users
Understanding Fingerprinting Vectors:
Websites collect:
- Screen resolution and color depth
- Installed fonts
- Browser plugins
- Time zone
- Language settings
- WebGL capabilities
- Canvas fingerprinting
- Audio context fingerprinting
How Tor Browser Mitigates:
- Standardized window sizes (letterboxing)
- Limited font set
- No plugins allowed
- Spoofed time zone
- Standard language
- Limited WebGL
- Canvas blocking
- Audio context blocking
Test Window Resizing:
- Try to maximize Tor Browser window
- Notice: Doesn’t fill entire screen
- Gray borders appear (letterboxing)
- Why: Prevents screen resolution fingerprinting
Hour 4: Onion Services and the Dark Web (11:00 AM - 12:00 PM)
Understanding .onion Sites
What are Onion Services?
- Websites hosted within Tor network
- End with .onion instead of .com, .org, etc.
- Provide anonymity for BOTH visitor and host
- Cannot be accessed without Tor
- Not indexed by regular search engines
Why Onion Services Matter:
For Users:
- End-to-end encryption (even exit node can’t see)
- No DNS lookup (more private)
- Censorship resistant
For Hosts:
- Server location hidden
- DDoS protection
- No need for domain registration
- Cannot be seized (no physical location to raid)
Legitimate Uses:
- Whistleblowing platforms (SecureDrop)
- News organizations (NYTimes, BBC, ProPublica)
- Privacy tools (DuckDuckGo onion)
- Human rights organizations
- Circumventing censorship
- Freedom of speech platforms
Exercise 7: Exploring Legitimate Onion Services (30 minutes)
Part A: Verified News Sites
- ProPublica Onion Service:
https://p53lf57qovyuvwsc6xnrppyply3vtqm7l6pcobkmyqsiofyeznfu5uqd.onion- Investigative journalism
- Same content as clearnet site
- More private for readers in repressive countries
- BBC News Onion:
https://www.bbcnewsd73hkzno2ini43t4gblxvycyac5aw4gnv7t2rccijh7745uqd.onion- International news
- Accessible in countries that block BBC
- Verifiably authentic BBC
- DuckDuckGo Onion:
https://duckduckgogg42xjoc72x3sjasowoarfbgcmvfimaftt6twagswzczad.onion- Private search engine
- No exit node sees your searches
- Faster than using exit nodes
Part B: Discovering Onion Services
The Hidden Wiki (use caution, verify URLs):
- Directory of onion services
- Mix of legitimate and questionable content
- Always verify onion addresses from trusted sources
Better Resources:
- Ahmia.fi - Onion search engine (clearnet accessible)
- dark.fail - Verified onion service directory
- Tor Project website - Official list of known services
Exercise: Verify an Onion Address
- Visit regular ProPublica site: https://www.propublica.org
- Find their onion address on their official site
- Compare with what I provided above
- Visit onion address
- Verify content matches
Why Verification Matters:
- Onion addresses are random-looking strings
- Easy to typo
- Phishing sites exist
- Always get addresses from trusted sources
Understanding Tor Circuit Information
View Current Circuit:
- In Tor Browser, click site information (padlock or info icon)
- Click “Connection” or circuit icon (looks like onion with paths)
- See your Tor circuit:
This Browser → Guard → Middle → Middle → Exit/Site
What You’re Seeing:
- Guard: Your entry to Tor (constant for 2-3 months)
- Middle relays: Change per circuit
- Exit: Where traffic leaves Tor (for clearnet sites)
- Onion service: No exit node (direct to service within Tor)
Exercise 8: Circuit Analysis (15 minutes)
- Visit a clearnet site (e.g., nytimes.com)
- View circuit
- Note: Guard → Middles → Exit → Site
- Exit node location matters (they see unencrypted traffic)
- Visit an onion site (e.g., DuckDuckGo onion)
- View circuit
- Note: Guard → Middles → Onion Service
- No exit node! End-to-end encrypted
- New Circuit for This Site:
- Right-click in Tor Browser
- “New Circuit for This Site”
- Circuit changes (new middle relays, possibly new exit)
- Use if: Site blocking Tor, slow connection, suspicion of compromise
Why This Matters: Understanding circuits helps you:
- Know when you’re truly anonymous (onion services)
- Identify potential surveillance points (exit nodes)
- Troubleshoot connection issues
- Make informed security decisions
Lunch Break (12:00 PM - 1:00 PM)
Take a real break! Walk away from computer.
Reflection Questions:
- How does browsing through Tor feel different?
- What surprised you about Tails’ approach to security?
- What threat model best describes your use case?
- What questions do you still have about anonymity?
Privacy Note: Even during lunch, consider:
- Don’t discuss specific onion sites in public
- Don’t take photos of your Tails screen
- Don’t post on social media that you’re using Tails
- Operational security extends beyond the computer
Afternoon Session (1:00 PM - 5:00 PM)
Hour 5: Persistent Storage and Data Management (1:00 - 2:00 PM)
Understanding Persistence in Tails
The Paradox:
- Tails is amnesic by default (forgets everything)
- But sometimes you need to save things (documents, settings, encryption keys)
- Persistence feature: Encrypted storage on your USB drive
What Persistence Can Store:
- Personal documents
- Browser bookmarks
- Email configuration
- Encryption keys (GnuPG)
- SSH keys
- Bitcoin wallet
- Additional software
- Application settings
What Stays Ephemeral:
- Tor Browser history (intentional)
- RAM contents
- Temporary files
- Most system changes
Creating Persistent Storage
Exercise 9: Configure Persistence (20 minutes)
Step 1: Enable Persistence
- Applications → Tails → Configure persistent volume
- Create Passphrase:
- Strong passphrase (20+ characters recommended)
- Write it down securely (lose it = lose data)
- This is NOT your administration password
- This encrypts your persistent storage
- Click “Create”
- Tails creates encrypted partition on USB
- Takes 1-3 minutes
- Size: Uses remaining space on USB (minus Tails system)
Step 2: Choose What to Persist
Personal Documents:
- ✓ Enable (you’ll want to save files)
- Saves: ~/Persistent/ folder contents
Browser Bookmarks:
- ✓ Enable (if you revisit same sites)
- Saves: Tor Browser bookmarks only
- Does NOT save history or cookies (security)
Network Connections:
- ✓ Enable (convenience)
- Remembers: WiFi passwords
- Security: Encrypted in persistence
GnuPG:
- ✓ Enable (essential for encryption)
- Saves: Your encryption keys
- Without this: Can’t decrypt old files after reboot
SSH Client:
- Enable if you use SSH
- Saves: SSH keys and known hosts
Bitcoin Client:
- Enable if you use Electrum
- Saves: Wallet and transaction history
Additional Software:
- Enable if you install custom packages
- Software persists across reboots
- Use cautiously (could compromise security)
Dotfiles:
- Advanced: Configuration files
- Enable if you customize system settings
Recommendation for Today: Enable:
- Personal Documents
- Browser Bookmarks
- Network Connections
- GnuPG
Step 3: Activate and Reboot
- Click “Save” after selecting features
- Restart Tails: Applications → Power → Restart
- At Welcome Screen:
- Unlock persistence with your passphrase
- Check “Unlock Encryption” before starting Tails
- Start Tails
After Reboot:
- Persistent folder appears in file manager
- Your settings are restored
- Bookmarks loaded in Tor Browser
Working with Persistent Storage
Exercise 10: Persistent Storage Practice (20 minutes)
Part A: Create Documents
- Open file manager (Files)
- Navigate to “Persistent” folder
- Create directory structure:
Persistent/ ├── Documents/ ├── Keys/ ├── Archives/ └── Work/ - Create test document:
- Open Text Editor (Activities → Text Editor)
- Write: “Testing persistence in Tails”
- Save to: Persistent/Documents/test.txt
- Create sensitive document:
- New document
- Write: “Sensitive information for encryption practice”
- Save to: Persistent/Documents/sensitive.txt
Part B: Add Bookmarks
- Open Tor Browser
- Visit sites you’ll reference:
- https://tails.net (Tails documentation)
- DuckDuckGo onion address
- ProPublica onion address
- Bookmark each (Ctrl+D or star icon)
- Organize bookmarks in folders
Part C: Verify Persistence
DON’T reboot yet - we’ll verify later after more work.
Important Notes:
Persistence is NOT Backup:
- USB drives fail
- Data can corrupt
- Always maintain separate backups of critical data
Persistence Reduces Security:
- More data stored = more to compromise if USB seized
- Trade-off: convenience vs. maximum security
- Consider: What truly needs to persist?
Persistence Encryption:
- Storage encrypted with your passphrase
- Strong passphrase critical
- Without passphrase: Data unrecoverable (this is a feature!)
Hour 6: Encryption and Cryptography Fundamentals (2:00 - 3:00 PM)
Understanding Encryption Types
Symmetric Encryption:
- Same key encrypts and decrypts
- Fast, efficient for large files
- Problem: How to share the key securely?
- Example: AES (Advanced Encryption Standard)
Asymmetric Encryption (Public Key Cryptography):
- Two keys: Public (shareable) and Private (secret)
- Public key encrypts → Private key decrypts
- Solves key sharing problem
- Example: RSA, GnuPG
The Genius of Public Key Crypto:
Alice wants to receive encrypted messages:
1. Alice generates key pair:
- Public key (anyone can have)
- Private key (Alice keeps secret)
2. Alice publishes public key
3. Bob encrypts message with Alice's public key
4. Only Alice's private key can decrypt
5. Even Bob can't decrypt his own message!
Digital Signatures:
- Proves message authenticity
- Reverse use of keys:
- Sign with private key
- Verify with public key
- Prevents impersonation
GnuPG (GPG) - OpenPGP Implementation
What is GPG?
- Free implementation of OpenPG standard
- Industry standard for email encryption
- Command-line and GUI tools
- Integrated into Tails
Exercise 11: Creating Your First GPG Key (25 minutes)
Step 1: Generate Key Pair
- Open Passwords and Keys:
- Activities → Passwords and Keys
- Or: Seahorse (older Tails versions)
-
Click + (plus icon) → GnuPG keys
- Enter Information:
- Full Name: Use pseudonym if desired (practice: “Tails User”)
- Email: Practice email (or leave blank)
- Comment: Optional description
- Click “Create”
- Set Passphrase:
- Protects your private key
- Strong passphrase essential
- Needed every time you decrypt or sign
- Wait for Key Generation:
- Takes 30-60 seconds
- Generating randomness for strong key
- Move mouse to add entropy
Step 2: Understanding Your Key
-
Right-click your key → Properties
- Key Details:
- Key ID: Unique identifier (last 8-16 characters of fingerprint)
- Fingerprint: Unique 40-character identifier
- Type: Usually RSA 3072 or 4096 bit
- Created: Date generated
- Expires: Expiration date (good practice: set expiration)
- Subkeys Tab:
- Master key: Certify and sign
- Subkey: Encrypt
- Separation increases security
Step 3: Export Public Key
- Right-click key → Export
- Save to: Persistent/Keys/my_public_key.asc
- This file is shareable (public key)
- Give this to people who want to send you encrypted messages
Step 4: Back Up Private Key
- Right-click key → Properties → Details
- Click “Export Complete Key”
- Save to: Persistent/Keys/my_private_key.asc
- This file is SECRET - never share!
- Protect it:
- Store on separate encrypted USB
- Paper backup (advanced)
- Never put online
Encrypting Files with GPG
Exercise 12: File Encryption Practice (20 minutes)
Method 1: GUI Encryption
- Create test file if not already:
- Persistent/Documents/sensitive.txt
- Add some “secret” text
-
Right-click file → Encrypt
- Choose encryption type:
- Sign/Encrypt with GPG
- Select your key
- Enter passphrase
- Encrypted file created:
- sensitive.txt.gpg
- Original remains unencrypted (delete if desired)
- Decrypt file:
- Right-click .gpg file → Open With → Decrypt File
- Enter passphrase
- Decrypted content appears
Method 2: Command Line Encryption
Open Terminal (Activities → Terminal):
# Navigate to documents
cd ~/Persistent/Documents
# Encrypt file (symmetric - password-based)
gpg -c test.txt
# Enter password when prompted
# Creates: test.txt.gpg
# Decrypt file
gpg test.txt.gpg
# Enter password
# Creates: test.txt (or prompts for output location)
# Encrypt with your GPG key (asymmetric)
gpg --encrypt --recipient "Tails User" sensitive.txt
# Creates: sensitive.txt.gpg
# Decrypt
gpg --decrypt sensitive.txt.gpg
# Enter key passphrase
# Shows decrypted content (doesn't save by default)
# Decrypt and save
gpg --decrypt sensitive.txt.gpg > decrypted.txt
Why Two Methods?
- Symmetric (password): Simple, good for personal files
- Asymmetric (GPG keys): Good for sharing, stronger security model
Best Practices:
- Delete original after encrypting (if truly sensitive)
shred -u original.txt # Secure deletion -
Use strong passphrases (20+ characters)
-
Never encrypt and leave decrypted version around
-
Test decryption before deleting originals
- Backup encryption keys securely
Hour 7: Secure Communication (3:00 - 4:00 PM)
Email Encryption with Thunderbird and OpenPGP
Why Email Encryption Matters:
Regular email is like a postcard:
- Anyone handling it can read it (ISPs, email providers, governments)
- Content is stored unencrypted on servers
- Subject lines never encrypted
- Metadata always visible (sender, recipient, time)
What OpenPGP Email Encryption Provides:
- ✓ Message body encrypted
- ✓ Attachments encrypted
- ✓ Sender authentication (digital signatures)
- ✗ Subject line still visible
- ✗ Metadata still visible (who, when, but not what)
Exercise 13: Thunderbird Email Setup (Practice Mode - 25 minutes)
Important Note: For true anonymous email, use Tor-based email services. This exercise focuses on encryption mechanics.
Step 1: Launch Thunderbird
- Activities → Thunderbird
- First launch shows welcome screen
Step 2: Configure Email (Use Temporary Account)
For practice, we’ll simulate without real account:
- Click “Skip this and use existing email”
- Enter practice details:
- Name: Tails Practice
- Email: practice@example.com (not real)
- Click “Configure manually”
- Server settings (practice values):
- Protocol: IMAP
- Server: mail.example.com
- Port: 993
- SSL: Yes
- Authentication: Normal password
- Don’t click “Done” - we’re just learning interface
Step 3: OpenPGP Integration
- Menu (≡) → Account Settings
- Select your account → End-to-End Encryption
- Add Key:
- Import existing key
- Select key you created earlier
- Enter passphrase
- Verify key loaded:
- Your key ID appears
- Fingerprint displayed
- Ready for encrypted email
Step 4: Understanding Encrypted Email Workflow
To Send Encrypted Email:
- Recipient must have GPG key
- You need their public key
- Compose message in Thunderbird
- Enable encryption (Security button → Encrypt)
- Send - only recipient’s private key can decrypt
To Receive Encrypted Email:
- You must share your public key with sender
- Encrypted message arrives
- Thunderbird prompts for your passphrase
- Message decrypts and displays
Exercise: Compose Practice Encrypted Message
- Click “Write” (new message)
- To: practice@example.com
- Subject: Testing OpenPGP (note: not encrypted)
- Body:
This is a test of OpenPGP encryption in Thunderbird. Only the message body and attachments are encrypted. The subject line and metadata remain visible. - Click Security → Require Encryption
- Attach file: Add a document from your Persistent folder
- Notice: Message will encrypt when sent
- Don’t actually send (we don’t have real account configured)
Why This Matters: Email encryption is standard for journalists, activists, lawyers, and anyone handling sensitive information. Understanding the mechanics prepares you for real-world secure communication.
Secure Messaging Alternatives
Email Limitations:
- Metadata always visible
- Subject lines not encrypted
- Server-stored messages vulnerable
- Complex key management
Better Alternatives for Real-Time Communication:
Signal (Not in Tails, but Important to Know):
- End-to-end encrypted
- Metadata minimal
- Easy to use
- Mobile-first
- Verified encryption
- Open source
OnionShare (Included in Tails):
- Share files anonymously through Tor
- No server intermediary
- Automatic .onion address
- Perfect for one-time secure transfers
Secure Drop (For Organizations):
- Whistleblower submission system
- Based on Tails and Tor
- Used by news organizations
- Air-gapped servers
- Source anonymity protected
Exercise 14: OnionShare File Sharing (20 minutes)
OnionShare creates temporary onion services for sharing files anonymously.
Step 1: Launch OnionShare
- Activities → OnionShare
- First launch may take moment to connect to Tor
Step 2: Share a File
- Select “Share Files”
- Click “Add Files”
- Choose a test file from Persistent/Documents
- Start Sharing:
- Click “Start Sharing”
- Wait for .onion address to generate
- Takes 30-60 seconds
Step 3: Understanding the Address
http://abc123def456ghi789.onion/secret-code
- abc123…onion: Your temporary onion service
- /secret-code: Random URL path (prevents guessing)
- Valid only while OnionShare running
Step 4: Share the Address
In real scenario:
- Copy address
- Send to recipient via secure channel (encrypted email, Signal, etc.)
- Recipient opens in Tor Browser
- Downloads file
- Connection is anonymous for both parties
Step 5: Receive Mode (Optional)
- Select “Receive Files”
- Start Receive Mode
- OnionShare creates upload page
- Share .onion address with sender
- They can upload files to you anonymously
- Files saved to your Persistent folder
Why OnionShare is Powerful:
- No server intermediary (direct peer-to-peer through Tor)
- No file size limits (unlike email)
- No account needed
- No logs
- Automatic .onion service
- Both parties anonymous
- Perfect for journalist-source communication
Security Considerations:
- Address is like a password (keep it secret)
- OnionShare must stay running (close laptop = connection lost)
- Temporary by design (addresses change each session)
- Use for one-time transfers, not permanent hosting
Hour 8: Advanced Privacy Techniques and Metadata (4:00 - 5:00 PM)
Understanding Metadata
Metadata: Data about data
Example: Digital Photo
The image itself: Content (what you see)
The metadata:
- Camera model
- Date and time taken
- GPS coordinates (location!)
- Camera settings
- Software used
- Edit history
- Thumbnail previews
Why Metadata is Dangerous:
Scenario: Activist photographs protest
- Content: Shows the protest (important)
- Metadata: Reveals exact location, time, and photographer’s camera
- Result: Government identifies photographer from camera signature
- Outcome: Arrested despite not appearing in photo
Real Example: John McAfee claimed to be hiding in Guatemala. Posted photo online. Metadata contained GPS coordinates. Location revealed. Had to flee.
Exercise 15: Metadata Analysis and Removal (25 minutes)
Part A: Examining Metadata
- Download a test image:
- In Tor Browser, visit: https://www.pexels.com
- Download any photo
- Save to: ~/Persistent/Documents/
- View metadata (Method 1: GUI):
- Right-click image → Properties
- Click “Image” tab
- See: Dimensions, color space
- Limited metadata shown
- View metadata (Method 2: Command Line):
cd ~/Persistent/Documents exiftool photo.jpg- Shows ALL metadata
- Camera, GPS, timestamps, software, etc.
Part B: Remove Metadata with MAT2
MAT2: Metadata Anonymisation Toolkit 2
- Launch MAT2:
- Right-click image → Remove metadata
- Or: Activities → Metadata Cleaner
-
Select files to clean
- Click “Clean”
- Creates cleaned version
- Original preserved (good for verification)
- Verify cleaning:
exiftool cleaned_photo.jpg- Minimal metadata remains
- Location, camera info removed
- Safe for anonymous sharing
Part C: Document Metadata
Documents also contain metadata:
Microsoft Word (.docx):
- Author name
- Organization
- Edit times
- Revision history
- Comments
- Hidden text
PDF Files:
- Creator software
- Author
- Creation date
- Modification date
- Producer
Exercise: Clean Document Metadata
- Create a test document:
- Open LibreOffice Writer
- Type some text
- File → Properties → Description
- Add: Author, title, comments
- Save as test.odt
- View metadata:
exiftool test.odt- See all the information!
- Clean with MAT2:
- Right-click → Remove metadata
- Or use MAT2 GUI
- Verify:
exiftool cleaned_test.odt
Best Practices:
Always Clean Before Sharing:
- Photos (especially phone photos with GPS)
- Documents (especially office files)
- PDFs (especially work documents)
- Videos (timestamps, GPS, camera info)
Prevention:
- Disable GPS in camera settings
- Remove author info from document templates
- Use plain text when possible (no metadata)
- Create documents in Tails (clean environment)
Network Traffic Analysis and Timing Attacks
What is Traffic Analysis?
Even with encryption, patterns reveal information:
Volume Analysis:
- Size of encrypted messages
- Small message = “yes/no” answer
- Large message = document transfer
- Pattern: Daily 500MB upload = likely cloud backup
Timing Analysis:
- When you connect
- How long you stay connected
- Pattern: Daily 9-5 connection = employee
- Pattern: Connection after whistleblower article = suspect identified
Correlation Attacks:
Scenario:
- Whistleblower uses Tails to submit document
- Government monitors all Tor users
- Document published at 3:00 PM
- Cross-reference: Who used Tor between 2-3 PM?
- Only 5 employees used Tor in that window
- Narrow suspects from 1000 to 5
- Investigation focuses on these 5
How to Mitigate:
Use Tails at Random Times:
- Not just when doing sensitive work
- Regular Tor use for normal browsing
- Creates noise in traffic patterns
Extend Sessions:
- Don’t disconnect immediately after sensitive action
- Browse normally for 30-60 minutes after
- Makes correlation harder
Use Public WiFi:
- Not traceable to your home
- Many people on same network
- But: Physical surveillance possible
- Trade-offs exist
Use Bridges (If Tor is Blocked):
- Unlisted Tor relays
- Not in public directory
- Harder to detect Tor usage
- Configure in Tails welcome screen
Exercise 16: Operational Security Assessment (20 minutes)
Evaluate Your OpSec Posture:
Scenario Planning:
For each scenario, identify risks:
Scenario 1: Journalist Meeting Source
- Risk: Physical surveillance of journalist
- Risk: Source’s phone location data
- Risk: Meeting at unusual location raises suspicion
- Mitigations?
- Meet in public, crowded place
- Both parties leave phones at home
- Arrive/leave separately
- Multiple meetings at same place (normal routine)
Scenario 2: Researching Sensitive Topic
- Risk: ISP sees Tor usage
- Risk: Timing correlates with work hours
- Risk: Change in behavior suspicious
- Mitigations?
- Use Tor regularly for all browsing
- Use public WiFi for sensitive research
- Maintain normal patterns
Scenario 3: Sharing Encrypted Document
- Risk: Metadata in document reveals you
- Risk: Writing style identifiable
- Risk: Document relates to your unique knowledge
- Mitigations?
- Clean all metadata with MAT2
- Modify writing style
- Remove identifying details
- Share through OnionShare, not email
Create Your Personal OpSec Checklist:
Write down your personalized security checklist:
BEFORE SENSITIVE ACTIVITY:
[ ] Boot Tails
[ ] Connect to public WiFi (if possible)
[ ] Enable persistent storage
[ ] Set security slider to "Safer" or "Safest"
[ ] Clear any identifying bookmarks
DURING ACTIVITY:
[ ] Stay on task (no personal accounts)
[ ] Take notes in encrypted file
[ ] Clean metadata from any files
[ ] Use .onion sites when available
[ ] Monitor Tor connection status
AFTER ACTIVITY:
[ ] Clean metadata from all files
[ ] Save important files to persistent storage
[ ] Encrypt sensitive documents
[ ] Browse normally for 30+ minutes
[ ] Shutdown (don't just close laptop)
NEVER:
[ ] Log into personal accounts
[ ] Share real identity information
[ ] Mention using Tails/Tor
[ ] Take screenshots of sensitive content
[ ] Connect to home WiFi for sensitive work
Evening Session (5:00 PM - 6:00 PM)
Final Hour: Real-World Applications and Mastery Verification
Exercise 17: Complete Privacy Workflow Simulation (30 minutes)
Scenario: You need to anonymously research and document information, then share it securely.
Step 1: Research Phase
- Set Tor Browser to “Safer” mode
- Research topic: (choose safe topic like “open source encryption”)
- Take notes:
- Open Text Editor
- Document findings
- Save to: Persistent/Documents/research_notes.txt
- Download supporting materials:
- Find relevant PDF or image
- Save to Persistent/Documents/
- Immediately clean metadata:
- Right-click → Remove metadata
Step 2: Document Creation Phase
- Open LibreOffice Writer
- Create report:
- Title: Your research topic
- Body: Summary of findings
- Insert: Cleaned image
- Format professionally
- Save as PDF:
- File → Export as PDF
- Save to Persistent/Documents/
- Clean PDF metadata:
- Use MAT2 on the PDF
- Verify cleaning with exiftool
Step 3: Encryption Phase
- Encrypt the PDF:
cd ~/Persistent/Documents gpg --encrypt --recipient "Tails User" report.pdf - Verify encryption:
- report.pdf.gpg created
- Original PDF unencrypted (consider deleting)
Step 4: Secure Sharing Phase
- Launch OnionShare
- Add encrypted file: report.pdf.gpg
- Start sharing
-
Copy .onion address
- Document instructions for recipient: ```
- Open in Tor Browser: [onion address]
- Download report.pdf.gpg
- Decrypt: gpg –decrypt report.pdf.gpg
- Enter passphrase: [share separately]
- Read decrypted PDF ```
Step 5: Cleanup Phase
- Secure delete unencrypted files:
shred -u report.pdf shred -u original_image.jpg - Keep encrypted versions:
- report.pdf.gpg (safe to store)
- cleaned_image.jpg (metadata removed)
- Document activity:
- Note what you did in research_notes.txt
- Encrypt notes file too if needed
What You’ve Demonstrated:
- Anonymous research through Tor
- Metadata awareness and removal
- Strong encryption
- Secure sharing
- Proper cleanup
This is the complete workflow for handling sensitive information.
Exercise 18: Tails Mastery Verification (20 minutes)
Test your knowledge:
Practical Skills Checklist:
Tor and Anonymity:
- Explained how Tor provides anonymity
- Identified what Tor protects and what it doesn’t
- Adjusted security slider appropriately
- Accessed .onion services
- Understood circuit information
- Recognized fingerprinting risks
Persistence and Storage:
- Created encrypted persistent storage
- Configured appropriate persistence features
- Organized files in persistent folder
- Understood persistence vs. amnesia trade-offs
Encryption:
- Generated GPG key pair
- Encrypted files with GPG
- Decrypted files with GPG
- Exported public key
- Backed up private key
- Understood symmetric vs. asymmetric encryption
Secure Communication:
- Configured Thunderbird with OpenPGP
- Understood encrypted email workflow
- Shared files with OnionShare
- Recognized secure communication alternatives
Metadata and OpSec:
- Identified metadata in files
- Removed metadata with MAT2
- Understood traffic analysis
- Created personal OpSec checklist
- Applied security workflow to complete task
Advanced Understanding:
- Explained threat models
- Recognized operational security failures
- Understood timing and correlation attacks
- Balanced security with usability
Common Mistakes and How to Avoid Them
Mistake 1: Mixing Identities
- ❌ Logging into personal email from Tails
- ❌ Using same pseudonym across contexts
- ✓ Keep anonymous identity completely separate
- ✓ Never link anonymous and personal accounts
Mistake 2: Metadata Oversight
- ❌ Sharing photos without cleaning metadata
- ❌ Documents with author name
- ✓ Always use MAT2 before sharing
- ✓ Verify cleaning with exiftool
Mistake 3: Pattern Recognition
- ❌ Only using Tor for sensitive activities
- ❌ Connecting at predictable times
- ✓ Use Tor regularly for normal browsing
- ✓ Vary your patterns
Mistake 4: Weak Passphrases
- ❌ Short passwords (password123)
- ❌ Personal information (birthday, name)
- ✓ 20+ character passphrases
- ✓ Random words or generated strings
- ✓ Use KeePassXC for password management
Mistake 5: Persistence Overuse
- ❌ Storing everything in persistent storage
- ❌ Treating Tails like regular OS
- ✓ Only persist what’s necessary
- ✓ Remember: More data = more exposure if compromised
Mistake 6: Trusting Technology Alone
- ❌ Tails makes me invincible
- ❌ Don’t need to worry about behavior
- ✓ Technology + OpSec = Security
- ✓ Human factor is most important
Mistake 7: Ignoring Physical Security
- ❌ Leaving Tails USB unlocked
- ❌ Using Tails in view of cameras
- ✓ Secure physical USB storage
- ✓ Be aware of surveillance cameras
- ✓ Use privacy screens
Advanced Topics and Resources
When to Use Tails vs. Other Privacy Tools
Use Tails When:
- Maximum anonymity required
- Whistleblowing or journalism
- Avoiding censorship
- Researching sensitive topics
- Leaving no trace on host computer
- Need complete privacy environment
Consider Alternatives When:
- Need mobile privacy (Signal, Briar)
- Daily communication (Matrix, XMPP)
- Persistent work environment needed (Qubes OS)
- Just need VPN-level privacy (Mullvad VPN)
- Tor too slow for large downloads
Qubes OS: The Next Level
What is Qubes?
- Security through compartmentalization
- Each task in separate VM
- Compromise contained to one VM
- Professional security researchers use it
- Learning curve steeper than Tails
When to Explore Qubes:
- After mastering Tails
- Need persistent secure environment
- Handle multiple sensitive identities
- Professional security work
The Tor Ecosystem
Related Projects:
Tor Browser Bundle:
- Tor Browser for regular OS
- Not as secure as Tails (host OS not trusted)
- More convenient for casual privacy
Whonix:
- Two VM system (Gateway + Workstation)
- Everything routed through Tor
- Run inside VirtualBox or Qubes
- More permanent than Tails
SecureDrop:
- Whistleblower platform
- Tails-based for sources
- Air-gapped server for journalists
- Used by major news organizations
Tails Limitations and Advanced Threats
What Tails Cannot Protect Against:
Global Passive Adversary:
- Entity that can monitor all internet traffic globally
- Could correlate Tor entry and exit
- Theoretical for most; real for nation-states
- Mitigation: Additional layers (bridges, VPNs carefully used)
Hardware Exploitation:
- Compromised computer firmware
- Hardware keyloggers
- Evil maid attacks (physical device access)
- Mitigation: Trusted hardware, physical security
Advanced Traffic Analysis:
- Long-term timing analysis
- Website fingerprinting (advanced)
- Patterns over months of usage
- Mitigation: Vary behavior, use bridges
Social Engineering:
- Tricking you into revealing identity
- Phishing for key passphrases
- Impersonation attacks
- Mitigation: Never reveal identity, verify contacts
Physical Coercion:
- Legal compulsion to reveal passwords
- Rubber-hose cryptanalysis (torture)
- Legal jurisdiction matters
- Mitigation: Plausible deniability (VeraCrypt hidden volumes)
Resources for Continued Learning
Official Documentation:
- https://tails.net/doc/
- Most comprehensive resource
- Updated with each release
- Security advisories
Training Materials:
- Security Education Companion (EFF)
- Surveillance Self-Defense (EFF)
- Digital Security for Journalists (CPJ)
Community:
- Tails support portal
- r/tails subreddit
- Tor Project community
- Local privacy/security meetups
Books:
- “The Smart Girl’s Guide to Privacy” - Violet Blue
- “Data and Goliath” - Bruce Schneier
- “Extreme Privacy” - Michael Bazzell
- “The Art of Invisibility” - Kevin Mitnick
Practice:
- Set up Tails for regular browsing
- Use encrypted email for real communications
- Practice OpSec in daily life
- Help others learn privacy tools
Conclusion: Your Privacy Journey Continues
Congratulations! You’ve completed intensive Tails training. You’ve learned:
✓ Threat modeling and privacy fundamentals ✓ Tor network architecture and anonymous browsing ✓ Persistent storage with strong encryption ✓ GPG encryption for files and email ✓ Metadata risks and removal techniques ✓ Secure communication methods ✓ Operational security principles ✓ Real-world privacy workflows
But This Is Just the Beginning:
Privacy is not a product—it’s a practice. The tools you learned today are only effective if you use them correctly and consistently.
Your Next Steps:
Week 1:
- Use Tails for daily browsing (normalize Tor usage)
- Practice GPG encryption with friends
- Set up encrypted email
- Clean metadata from all shared files
Month 1:
- Develop personal OpSec protocols
- Research your specific threat model
- Explore advanced Tails features
- Consider Qubes OS or Whonix
Ongoing:
- Stay updated on privacy news
- Follow Tails security advisories
- Practice security culture
- Help others learn privacy tools
- Never stop learning
Remember the Fundamentals:
- Technology alone is not enough - OpSec matters
- Perfect security doesn’t exist - manage risk
- Convenience vs. Security - conscious trade-offs
- Behavior matters most - don’t reveal yourself
- Privacy is a right - worth protecting
Appendix: Quick Reference
Tails Boot Options
Standard Boot: Normal Tails session
Troubleshooting: For hardware issues
Offline Mode: No network connection
Unsafe Browser: Only for captive portals
Tor Browser Security Levels
Standard: All features, best compatibility
Safer: JavaScript on HTTPS only
Safest: No JavaScript, maximum security
Essential Commands
# GPG Encryption
gpg -c file.txt # Symmetric encryption
gpg --encrypt --recipient "Name" file.txt # Asymmetric
gpg --decrypt file.txt.gpg # Decrypt
# Metadata Removal
exiftool file.jpg # View metadata
mat2 file.jpg # Remove metadata
# Secure Deletion
shred -u file.txt # Secure delete
# Check Tor Connection
systemctl status tor@default # Tor service status
Keyboard Shortcuts
Tor Browser:
Ctrl+Shift+U New Tor circuit for site
Ctrl+Shift+L New Tor identity (relaunch)
Ctrl+Shift+N New private window
GNOME Desktop:
Alt+F2 Run command
Alt+Tab Switch windows
Super Activities overview
Important Directories
~/Persistent Your persistent storage
/home/amnesia Home directory (ephemeral)
/live/persistence Persistent volume mount point
Tails-Specific Paths
Persistent storage location: /live/persistence/TailsData_unlocked
Tor Browser profile: /home/amnesia/.tor-browser/
GnuPG keys: ~/Persistent/gnupg
Your Day 2 Completion Checklist
Morning Session:
- Understood threat models
- Configured Tails securely
- Mastered Tor Browser security levels
- Explored .onion services
- Analyzed browser fingerprinting
Afternoon Session:
- Created encrypted persistent storage
- Generated GPG key pair
- Encrypted and decrypted files
- Configured Thunderbird for encrypted email
- Shared files anonymously with OnionShare
- Removed metadata from files
Evening Session:
- Understood operational security principles
- Completed full privacy workflow
- Created personal OpSec checklist
- Identified common mistakes
- Documented learning journey
Advanced Understanding:
- Explained how Tor works
- Recognized Tails’ limitations
- Understood timing and correlation attacks
- Balanced security with usability
- Committed to ongoing privacy practice
Final Exercise: Your Privacy Commitment
Create a personal privacy plan:
MY PRIVACY COMMITMENT
I will use Tails when:
- [Specific use cases]
I will practice these OpSec principles:
- [Your personal rules]
I will avoid these mistakes:
- [Common pitfalls to watch for]
I commit to learning:
- [Next privacy topics to explore]
My threat model:
- Who: [Your adversaries]
- What: [Information to protect]
- How: [Protection methods]
Signed: [Your pseudonym]
Date: [Today's date]
Where to Go From Here
Immediate Actions:
- Save this guide to encrypted persistent storage
- Practice with Tails weekly
- Set up encrypted email account
- Join privacy-focused communities
Short-term Goals (1-3 months):
- Master GPG for all sensitive communication
- Develop consistent OpSec habits
- Help friend learn Tails
- Explore Signal for mobile privacy
Long-term Goals (3-12 months):
- Investigate Qubes OS
- Learn about cryptocurrency privacy
- Study advanced cryptography
- Contribute to privacy projects
Remember: Privacy is not paranoia. It’s a fundamental human right. By mastering tools like Tails, you’re protecting not just yourself, but everyone who depends on secure communication.
Stay safe. Stay anonymous. Stay free.
Document Version: 1.0
Created: Day 2 of Linux Mastery Series
Previous: Day 1 - Puppy Linux
Next Guide: Day 3 - Kali Linux for Security Professionals
For updates: Visit tails.net for latest Tails documentation
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