cypherpunk-cheats/email-privacy.cheat

% email, privacy, protonmail, tutanota, pgp, encryption

# ============================================================================
# EMAIL PRIVACY OVERVIEW
# ============================================================================

# Email privacy challenges
# - Metadata always visible (sender, recipient, timestamp, IP)
# - Content readable by email provider (unless E2EE)
# - Subject lines never encrypted
# - Forwarding/CC/BCC creates multiple copies
# - Email headers reveal technical information

# Privacy hierarchy (best to worst)
# 1. Self-hosted encrypted email (high effort)
# 2. ProtonMail / Tutanota (E2EE, Switzerland/Germany)
# 3. Mailfence (Belgian, PGP support)
# 4. FastMail (Australian, privacy-focused but not E2EE)
# 5. Gmail / Outlook (convenient, zero privacy)

# ============================================================================
# PROTONMAIL (END-TO-END ENCRYPTED EMAIL)
# ============================================================================

# ProtonMail features
# - Zero-access encryption (provider can't read emails)
# - Swiss jurisdiction (strong privacy laws)
# - Open source clients
# - Tor onion service available
# - No logging of IP addresses (with some caveats)

# Sign up for ProtonMail
# https://proton.me/mail

# Free tier limits
# - 500 MB storage
# - 150 messages per day
# - 1 email address
# - Limited support

# Paid tier benefits
# - More storage (15 GB - 500 GB)
# - Custom domains
# - Multiple addresses
# - ProtonVPN included (Plus and higher)

# ProtonMail encryption
# ProtonMail ↔ ProtonMail: Automatic E2EE
# ProtonMail ↔ Other: Optional password-protected encryption

# Send encrypted email to non-ProtonMail user
# Compose → Lock icon → Set password → Share password separately

# ProtonMail Bridge (desktop email client)
# Allows using ProtonMail with Thunderbird, Apple Mail, Outlook
# https://proton.me/mail/bridge

# Install ProtonMail Bridge (Linux)
wget https://proton.me/download/bridge/protonmail-bridge_amd64.deb
sudo dpkg -i protonmail-bridge_amd64.deb

# Configure Thunderbird with Bridge
# Bridge → Add account → Copy IMAP/SMTP settings → Add to Thunderbird

# ============================================================================
# TUTANOTA (GERMAN E2EE EMAIL)
# ============================================================================

# Tutanota features
# - End-to-end encryption (email + subject line + contacts)
# - German jurisdiction (GDPR compliance)
# - Open source
# - No third-party trackers
# - Encrypted calendar included

# Sign up for Tutanota
# https://tutanota.com/

# Free tier
# - 1 GB storage
# - 1 email address
# - 48-hour support response

# Paid tier benefits
# - More storage (20 GB - 1 TB)
# - Custom domains
# - Aliases (up to 100)
# - Faster support

# Tutanota encryption
# Tutanota ↔ Tutanota: Automatic E2EE (subject included)
# Tutanota ↔ Other: Optional password-protected E2EE

# Tutanota desktop app
# Download: https://tutanota.com/download/

# ============================================================================
# EMAIL ALIASING (HIDE REAL ADDRESS)
# ============================================================================

# Email alias services
# Protect primary email, prevent tracking, reduce spam

# SimpleLogin (recommended)
# https://simplelogin.io/
# - Unlimited aliases (Premium)
# - Reply from alias
# - PGP support
# - Open source

# Sign up for SimpleLogin
# https://simplelogin.io/

# Create alias
# Dashboard → New alias → Enter name → Create

# AnonAddy (alternative)
# https://anonaddy.com/
# - Similar to SimpleLogin
# - Self-hostable

# Firefox Relay (Mozilla)
# https://relay.firefox.com/
# - Free tier: 5 aliases
# - Premium: Unlimited aliases

# Apple Hide My Email (iOS/macOS)
# Settings → iCloud → Hide My Email
# Generates random addresses that forward to real email

# DuckDuckGo Email Protection
# https://duckduckgo.com/email/
# - Free
# - Removes trackers from emails

# ============================================================================
# PGP/GPG EMAIL ENCRYPTION
# ============================================================================

# PGP/GPG for any email provider
# See gpg.cheat for full key management guide

# Generate PGP key
gpg --full-generate-key

# Export public key (share with contacts)
gpg --armor --export <your_email> > publickey.asc
$ your_email: echo "you@example.com"

# Import contact's public key
gpg --import <contact_publickey.asc>
$ contact_publickey.asc: echo "friend_key.asc"

# Encrypt email message
echo "Secret message" | gpg --encrypt --armor --recipient <contact_email> > encrypted.asc
$ contact_email: echo "friend@example.com"

# Decrypt received email
gpg --decrypt encrypted_email.asc

# ============================================================================
# THUNDERBIRD WITH PGP (ENIGMAIL/OPENPGP)
# ============================================================================

# Install Thunderbird
sudo apt install thunderbird

# Built-in OpenPGP support (Thunderbird 78+)
# No Enigmail extension needed

# Generate key in Thunderbird
# Account Settings → End-To-End Encryption → Add Key
# Generate new key

# Import existing PGP key
# Account Settings → End-To-End Encryption → Add Key
# Import key from file

# Send encrypted email
# Compose → Options → Encrypt message
# Select recipient's public key

# Sign email
# Compose → Options → Digitally sign message

# ============================================================================
# MAILFENCE (PGP-COMPATIBLE SECURE EMAIL)
# ============================================================================

# Mailfence features
# - Belgian jurisdiction (privacy-friendly)
# - Built-in PGP support
# - Digital signatures
# - No ads
# - 2FA support

# Sign up for Mailfence
# https://mailfence.com/

# Mailfence pricing
# Free: 500 MB storage
# Entry ($2.50/mo): 5 GB storage, custom domain
# Pro ($7.50/mo): 20 GB, advanced features

# Import PGP key to Mailfence
# Settings → Security → Encryption → Import key

# Send encrypted email
# Compose → Encrypt (lock icon) → Send

# ============================================================================
# TEMPORARY/DISPOSABLE EMAIL
# ============================================================================

# Use for signups, one-time registrations

# 10 Minute Mail
# https://10minutemail.com/
# Temporary email (10 minutes, extendable)

# Guerrilla Mail
# https://www.guerrillamail.com/
# Disposable email, can send/receive

# Temp Mail
# https://temp-mail.org/
# Random temporary address

# Burner Mail
# https://burnermail.io/
# Create disposable forwarding addresses

# ============================================================================
# EMAIL HEADER ANALYSIS (PRIVACY LEAKS)
# ============================================================================

# Email headers reveal
# - Originating IP address
# - Email client software
# - Mail server path
# - Timestamps

# View email headers (Thunderbird)
# Open email → More → View Source

# View email headers (Gmail web)
# Open email → Three dots → Show original

# Common header fields
# From: Sender address
# To: Recipient address
# Subject: Email subject (never encrypted)
# Date: Timestamp
# Received: Mail server path (contains IP addresses)
# X-Originating-IP: Sender's IP address

# Analyze headers for privacy leaks
# Look for: Real IP, location data, identifying info

# Strip revealing headers (when forwarding)
# Use email provider's privacy features
# Or: Copy content to new email (don't forward)

# ============================================================================
# EMAIL TRACKER BLOCKING
# ============================================================================

# Email tracking pixels
# Invisible 1x1 pixel images embedded in emails
# Reports when email opened, device type, location

# Blocking trackers (Thunderbird)
# Preferences → Privacy → Mail Content → Block remote content

# DuckDuckGo Email Protection
# Automatically removes trackers from emails
# https://duckduckgo.com/email/

# Hey.com (tracker blocking built-in)
# https://www.hey.com/
# $99/year, strong privacy features

# ============================================================================
# EMAIL PROVIDER COMPARISON
# ============================================================================

# ProtonMail
# Pros: E2EE, Swiss privacy, Tor support, open source
# Cons: Web only (unless Bridge), Bridge requires paid account
# Cost: Free tier available, paid from $4/mo

# Tutanota
# Pros: E2EE (including subject), German privacy, open source
# Cons: Less integration with other apps, custom protocol
# Cost: Free tier available, paid from €1/mo

# Mailfence
# Pros: Standard protocols (IMAP/SMTP), PGP support, Belgian privacy
# Cons: Not zero-knowledge (provider can access if compelled)
# Cost: Free tier available, paid from $2.50/mo

# Posteo
# Pros: Anonymous signup (no personal info required), green energy, ethical
# Cons: No free tier, basic features
# Cost: €1/mo

# StartMail
# Pros: Privacy focus, PGP support, disposable aliases
# Cons: Netherlands jurisdiction
# Cost: $59.95/year

# ============================================================================
# SELF-HOSTED EMAIL (MAXIMUM CONTROL)
# ============================================================================

# Self-hosted email advantages
# - Complete control over data
# - No third-party access
# - Custom configuration

# Self-hosted email disadvantages
# - Complex setup and maintenance
# - Spam filtering challenges
# - Deliverability issues (blacklists)
# - Server costs

# Mail-in-a-Box (easy self-hosted email)
# https://mailinabox.email/
# One-command installation
# Ubuntu 22.04 required

# Install Mail-in-a-Box
curl -s https://mailinabox.email/setup.sh | sudo bash

# Mailcow (Docker-based email server)
# https://mailcow.email/
# Modern web UI, comprehensive features

# ============================================================================
# EMAIL OPSEC BEST PRACTICES
# ============================================================================

# Separate email accounts by identity
# Personal: Real name email
# Work: Work email
# Anonymous: ProtonMail / Tutanota
# Signups: Disposable / alias

# Never link identities
# Don't use personal email for anonymous activities
# Don't reference other accounts in emails

# Subject line privacy
# Never put sensitive info in subject
# Subject always visible (even with PGP)
# Tutanota encrypts subjects (ProtonMail doesn't)

# Avoid email for highly sensitive communication
# Use Signal, Element, or other E2EE messengers
# Email has inherent metadata leakage

# Use aliases for online accounts
# SimpleLogin, AnonAddy for account signups
# Prevents tracking across services

# ============================================================================
# METADATA MINIMIZATION
# ============================================================================

# Email metadata always visible to provider
# - Sender, recipient, timestamp
# - IP addresses (in headers)
# - Email size

# Reduce metadata leakage
# Use Tor when accessing webmail (hides IP)
# Use VPN (hides IP from email provider)
# Use ProtonMail / Tutanota (minimal logging)

# Tor with ProtonMail
# ProtonMail onion service: https://protonmailrmez3lotccipshtkleegetolb73fuirgj7r4o4vfu7ozyd.onion/

# Tor with Tutanota
# Use Tor Browser to access: https://tutanota.com/

# ============================================================================
# PROTONMAIL ADVANCED FEATURES
# ============================================================================

# Custom domain (paid plans)
# Settings → Domains → Add domain
# Configure DNS records (MX, SPF, DKIM)

# ProtonMail import/export
# Settings → Import-Export → Import emails
# Supports: Gmail, Outlook, Yahoo

# ProtonMail filters (paid plans)
# Settings → Filters → Add filter
# Auto-organize incoming mail

# ProtonMail encrypted contacts
# Contacts stored with zero-access encryption
# Can't be read by ProtonMail

# ProtonMail VPN integration
# ProtonVPN included with Plus and higher plans
# Unified account management

# ============================================================================
# TUTANOTA ADVANCED FEATURES
# ============================================================================

# Encrypted calendar
# Calendar tab → Create event
# E2EE, syncs across devices

# Secure password reset
# Can disable password reset (maximum security)
# Settings → Security → Disable password reset
# WARNING: If you forget password, account is unrecoverable

# Tutanota for business
# Custom domain, team management
# Admin console for organization

# Tutanota whitelist mode
# Settings → Security → Whitelist
# Only receive emails from approved senders

# ============================================================================
# SECURING EMAIL ON MOBILE
# ============================================================================

# ProtonMail app (iOS/Android)
# Download: App Store / Play Store / F-Droid
# F-Droid (open source): https://f-droid.org/

# Tutanota app (iOS/Android)
# Download: App Store / Play Store / F-Droid

# K-9 Mail (Android, open source)
# Supports PGP via OpenKeychain
# https://k9mail.app/

# Install K-9 Mail + OpenKeychain
# F-Droid → K-9 Mail, OpenKeychain
# Import PGP key to OpenKeychain
# Configure K-9 to use OpenKeychain

# FairEmail (Android, privacy-focused)
# https://email.faircode.eu/
# Tracker blocking, encryption support

# ============================================================================
# EMAIL MIGRATION
# ============================================================================

# Migrating to secure email

# Step 1: Set up new secure email
# ProtonMail, Tutanota, or Mailfence

# Step 2: Import old emails (optional)
# ProtonMail Bridge → Import via IMAP
# Or: Manually forward important emails

# Step 3: Update accounts gradually
# Start with new signups
# Update critical services (banking, social media)
# Notify contacts

# Step 4: Set up forwarding (temporary)
# Old email → New email
# Gradually phase out old address

# Step 5: Close old account
# After 6-12 months of forwarding
# Delete or abandon old account

# ============================================================================
# EMAIL PRIVACY CHECKLIST
# ============================================================================

# Setup
# [ ] Choose privacy-focused provider (ProtonMail / Tutanota)
# [ ] Enable 2FA on email account
# [ ] Set up email aliases (SimpleLogin / AnonAddy)
# [ ] Import PGP keys (if using)
# [ ] Configure email client securely

# Daily use
# [ ] Use aliases for new signups
# [ ] Don't put sensitive info in subject lines
# [ ] Verify recipient before sending sensitive info
# [ ] Use disappearing messages for sensitive topics (Signal instead)

# Maintenance
# [ ] Review connected services quarterly
# [ ] Delete old unnecessary emails
# [ ] Update PGP keys before expiration
# [ ] Check for data breaches (haveibeenpwned.com)

# ============================================================================
# RESOURCES
# ============================================================================

# Privacy email guides
# EFF Email Self-Defense: https://emailselfdefense.fsf.org/
# Privacy Guides Email: https://www.privacyguides.org/email/

# Email security testing
# Email Privacy Tester: https://www.emailprivacytester.com/

# PGP key servers
# keys.openpgp.org
# keyserver.ubuntu.com

# Communities
# r/ProtonMail (Reddit)
# r/tutanota (Reddit)
# r/privacy (Reddit)