Email Privacy

Gmail reads every email you send and receive.

That’s not an exaggeration. Google scans your emails to:

Build advertising profiles
Train AI models on your conversations
Track purchase history and receipts
Identify your contacts and relationships
Monitor your location through confirmation emails

Google knows more about your life than your closest friends. They know when you’re job hunting (LinkedIn alerts), having health issues (doctor appointment confirmations), traveling (flight confirmations), and buying things (every receipt).

Your email is the master key to your digital life. Password resets, 2FA codes, account confirmations—everything flows through email. If your email is compromised, everything is compromised.

This week, you’ll move to encrypted email and set up email aliases to compartmentalize your identity.

The Email Privacy Problem

Gmail Is Surveillance

When you use Gmail (or Outlook, Yahoo, etc.), you’re giving a corporation complete access to your private communications.

What Gmail collects:

Every sender and recipient
Subject lines and full message content
Attachments and files
Timestamps and frequency of communication
IP addresses and device information
Browsing activity (if you clicked links in emails)

How they use it:

Ad targeting across Google properties
Building shadow profiles of non-Gmail users you email
Training AI models (yes, GPT alternatives are trained on your Gmail)
Selling insights to advertisers and data brokers

The Terms of Service are clear: “Our automated systems analyze your content to provide you personally relevant product features, such as customized search results, tailored advertising…”

Translation: We read everything.

Email Address as Identity

Your email address is tied to everything:

Social media accounts
Banking and financial services
Shopping and subscriptions
Work and professional contacts
Personal relationships

When you use one email for everything, you create a unified profile. One breach links all your accounts. One leak connects your work life to your personal life to your anonymous forum activity.

We’ll fix this with aliases.

Part 1: Choosing a Private Email Provider

We’ll cover two excellent options: Proton Mail and Tutanota. Both are:

End-to-end encrypted
Zero-access (they can’t read your emails)
Based in privacy-friendly countries
Open source

Proton Mail (Recommended)

Based in: Switzerland (strong privacy laws)

Encryption:

End-to-end encrypted by default
Zero-access encryption (Proton can’t decrypt your emails)
PGP-compatible for emailing other PGP users

Free tier includes:

1 GB storage
150 messages per day limit
1 email address
Limited support

Paid plans ($5-24/month):

More storage (15 GB - 500 GB)
Custom domains
Multiple email addresses
ProtonVPN bundled
Calendar and Drive included

Pros:

✅ Mature, well-audited service
✅ Large user base
✅ PGP interoperability
✅ Good mobile apps
✅ Integrated VPN, calendar, drive

Cons:

⚠️ Free tier is limited (150 emails/day)
⚠️ Search doesn’t work on encrypted email bodies (by design)

Best for: Most users, especially those wanting an all-in-one privacy suite

Tutanota

Based in: Germany (GDPR protection)

Encryption:

End-to-end encrypted (including subject lines!)
Zero-access encryption
Custom encryption (not PGP, more modern)

Free tier includes:

1 GB storage
1 email address
Full search (encrypted search index)
Calendar included

Paid plans ($3-9/month):

More storage (up to 20 GB)
Custom domains
Multiple addresses
Whitelabel options

Pros:

✅ Encrypts subject lines (Proton doesn’t)
✅ Very affordable paid tiers
✅ Cleaner, simpler interface
✅ Full-text search works on encrypted emails

Cons:

⚠️ Not PGP-compatible (proprietary encryption)
⚠️ Smaller ecosystem than Proton
⚠️ Less name recognition

Best for: Budget-conscious users, those wanting encrypted subject lines

Decision Guide

Choose Proton Mail if:

You want PGP compatibility
You need VPN/Calendar/Drive integration
You prefer a larger, more established service
Budget isn’t a concern

Choose Tutanota if:

You want subject lines encrypted
Budget matters ($3/month vs $5/month)
You prefer simplicity over features
PGP compatibility doesn’t matter to you

For this tutorial, we’ll use Proton Mail (more widely adopted), but setup is similar for Tutanota.

Part 2: Setting Up Proton Mail

Create Your Account

Open Firefox in your Linux Mint VM
Go to https://proton.me/mail
Click Get Proton Mail Free

Choose your plan:
- Start with Free (you can upgrade later)
Choose your username:
- Don’t use your real name (e.g., avoid [email protected])
- Use something neutral (e.g., cipher_wanderer, pixel_nomad)
- This is permanent, choose carefully

Create a strong password:
- Use your password manager (from Week 4)
- Generate a 20+ character random password
- Save it in KeePassXC or Bitwarden immediately
Select a recovery method:
- Email recovery: Use an existing email (Gmail, for now)
- Or Phone recovery: Use your phone number
- Or Skip (risky—if you forget password, you lose everything)
Complete CAPTCHA verification
Click Create Account

Initial Setup

After account creation:

Set up recovery method (if you skipped it)
- Settings → Recovery
- Add a recovery email or phone
- This is only for password reset, not for reading your emails
Enable Two-Factor Authentication
- Settings → Security
- Enable Two-factor authentication
- Use an authenticator app (Aegis on Android, Raivo OTP on iOS)
- Save backup codes in your password manager
Configure display name
- Settings → Identity and addresses
- Set your display name (the name people see when you email them)
- You can use a real name or pseudonym depending on use case

Understanding Proton Mail’s Encryption

Internal emails (Proton to Proton):

Automatically end-to-end encrypted
Proton cannot read them
Subject lines visible to Proton (metadata)

External emails (Proton to Gmail):

Not end-to-end encrypted by default
Stored encrypted on Proton’s servers
Recipient sees it in plain text in Gmail
You can enable “Encrypt for outside” (password-protected message)

PGP emails (Proton to PGP user):

Fully end-to-end encrypted
Both parties exchange public keys
Proton can’t read, recipient’s provider can’t read

We’ll cover PGP in detail in Week 9.

Part 3: Email Aliases for Compartmentalization

Now that you have a private email, don’t give it to everyone. Use aliases to compartmentalize your identity.

Why Aliases Matter

Problem: You give [email protected] to:

Shopping sites
Forums
Work contacts
Friends
Banks

Now:

Data breach at a shopping site exposes your main email
Spammers sell your email to 50 lists
You can’t tell who leaked your address
All these contexts are linked together

Solution: Use a different alias for each context:

[email protected] → Amazon
[email protected] → eBay
[email protected] → Reddit
[email protected] → LinkedIn
[email protected] → Real address for trusted contacts only

Benefits:

If [email protected] gets spam, you know Amazon leaked it
You can disable that alias without affecting others
Each context is isolated
Data breaches don’t reveal your real email

Alias Services: SimpleLogin vs AnonAddy

Both are open-source email aliasing services. Both work with Proton Mail.

SimpleLogin (Recommended)

Now owned by Proton (integrated with Proton Mail)
Free tier: 10 aliases
Premium: Unlimited aliases, custom domains ($30/year)
Browser extension for generating aliases on-the-fly

AnonAddy

Independent, open source
Free tier: Unlimited aliases, 10 MB bandwidth/month
Premium: More bandwidth, custom domains ($12/year)
More technical, more control

We’ll use SimpleLogin (better Proton integration).

Part 4: Setting Up SimpleLogin

Create SimpleLogin Account

Go to https://simplelogin.io/
Click Sign in with Proton
Authorize the connection
SimpleLogin is now linked to your Proton Mail account

All emails sent to SimpleLogin aliases forward to your Proton Mail inbox.

Create Your First Alias

In SimpleLogin dashboard, click New Alias
Two options:
- Random alias: SimpleLogin generates a random name (e.g., [email protected])
- Custom alias: You choose the name (e.g., [email protected])
For shopping sites, use custom:
- Alias: shop-amazon
- Suffix: @simplelogin.co (or your custom domain if you have premium)
- Note: “Amazon shopping”
- Click Create

The alias is created. All emails to [email protected] now forward to your Proton Mail.

Alias Naming Strategy

Organize by category:

shop-[sitename] → Shopping sites
forum-[sitename] → Forums and communities
social-[sitename] → Social media
work-[company] → Work-related
newsletter-[name] → Newsletters and subscriptions
temp-[purpose] → Temporary, disposable aliases

Example aliases:

[email protected]
[email protected]
[email protected]
[email protected]
[email protected]
[email protected]
[email protected]

Browser Extension for Quick Aliases

Install SimpleLogin browser extension in Firefox
When signing up for a site:
- Click the extension icon in email field
- Click Generate new alias
- It auto-fills a random alias
- Save it in your password manager
Email to that alias forwards to your Proton Mail inbox

Replying Through Aliases

When someone emails your alias, you can reply through the alias:

You receive email in Proton Mail from [email protected]
Click Reply
Your reply automatically goes through the alias
Recipient sees it coming from [email protected], not your real Proton address

Your real email stays hidden.

Disabling Aliases

If an alias gets spam:

Go to SimpleLogin dashboard
Find the alias
Click Disable (or Delete)
Emails to that alias are now blocked

The rest of your aliases keep working.

Part 5: Migrating from Gmail

You don’t need to delete Gmail immediately. Transition gradually.

Phase 1: New Accounts Use Proton + Aliases

Starting today:

New signups → Use SimpleLogin aliases
Existing accounts → Keep Gmail for now

Phase 2: Migrate Critical Accounts

Over the next few weeks, update your email on:

Priority 1 (do first):

Banking and financial accounts
Password manager account (if using Bitwarden)
Domain registrars
Any account with 2FA enabled

Priority 2 (next):

Social media (but use aliases!)
Shopping accounts (use aliases!)
Work-related accounts

Priority 3 (low priority):

Newsletters (use aliases, or just unsubscribe)
Old forums you never use

Phase 3: Forward Gmail to Proton

Set up forwarding so you don’t miss anything:

In Gmail, go to Settings → Forwarding and POP/IMAP
Click Add a forwarding address
Enter your Proton Mail address
Verify the forwarding (check Proton inbox)
Set Gmail to Forward a copy and Keep Gmail’s copy in Inbox

Now Gmail emails arrive in both Gmail and Proton. Over time, fewer emails arrive as you migrate accounts.

Phase 4: Monitor and Sunset Gmail

After 3-6 months:

Check which accounts still email your Gmail
Migrate any you care about
Eventually stop checking Gmail
Don’t delete Gmail (you might need password resets for old accounts)

Part 6: Email Best Practices

Send Encrypted Emails to Non-Proton Users

Proton lets you send password-protected emails to anyone:

Compose email in Proton Mail
Click the lock icon (Encrypt for outside)
Set a password (share this password via Signal or in-person)
Send email
Recipient gets a link to decrypt the email using the password

The email is encrypted in transit and at rest. Only someone with the password can read it.

Avoid Email for Sensitive Communications

Email is better than Gmail, but still not ideal for highly sensitive conversations:

Use email for:

Confirmations and receipts
Password resets
Account notifications
General communication

Don’t use email for:

Confidential documents (use encrypted file sharing instead)
Private conversations (use Signal, covered in Week 7)
Anything you wouldn’t want read in court

Email leaves metadata trails (who, when, subject line).

Unsubscribe from Everything

Newsletters clutter your inbox and expose your email:

Click Unsubscribe on unwanted newsletters
Use newsletter-[name]@simplelogin.co aliases for newsletters you want
You can disable the alias later if it gets annoying

Check for Email in Data Breaches

Use Have I Been Pwned regularly:

https://haveibeenpwned.com/

Enter your email addresses (including aliases) to see if they appear in breaches.

If your alias appears:

Disable it in SimpleLogin
Create a new alias for that service
Update your password for that account

Part 7: Mobile Email Setup

Install Proton Mail on your phone for on-the-go access.

Android

Use F-Droid (open-source app store) if available, or Google Play Store
Search Proton Mail
Install and log in
Enable notifications for important emails

iOS

Search Proton Mail in App Store
Install and log in
Enable notifications

Mobile Tips

Use Proton Mail app instead of default Mail app
Disable Gmail app notifications
Keep phone screen locked (emails are stored encrypted on device)

Privacy Checkpoint

Your email is now significantly more private:

What changed:

Moved from Gmail to end-to-end encrypted email
Set up aliases to compartmentalize identity
Enabled 2FA on email account
Started migrating accounts off Gmail

What you gained:

Proton/Tutanota can’t read your emails
Aliases prevent tracking across services
Data breaches are contained to single aliases
No more ad targeting based on email content

What you lost:

Gmail’s search (less powerful on encrypted email)
Unlimited storage (free tiers are limited)
Convenience of one email address (aliases require management)

The trade-off is worth it.

Troubleshooting

Proton Mail isn’t receiving emails

Check:

Spam folder in Proton
Whether the sender is blocked
Storage quota (free tier: 1 GB)

SimpleLogin alias not forwarding

Check:

Alias is enabled (not disabled/deleted)
SimpleLogin linked to correct Proton account
No bounces (sender might be blocked by Proton)

I forgot my Proton Mail password

If you set up recovery email/phone:

Go to https://account.proton.me/
Click Forgot password
Use recovery method

If no recovery method:

Your account is gone forever
This is by design (zero-access encryption)
Use your password manager to avoid this

Sites reject my alias

Some sites block @simplelogin.co addresses:

Use a custom domain (requires SimpleLogin premium)
Or use your Proton address directly for that site

Gmail forwarding stopped working

Gmail sometimes disables forwarding:

Check Gmail Settings → Forwarding
Re-verify if needed
Or manually check Gmail weekly

Going Further (Optional)

Custom Domain with Proton

With Proton Plus ($5/month), use your own domain:

Buy a domain (e.g., yourname.com)
In Proton settings, add custom domain
Configure DNS records (Proton provides instructions)
Now you can use [email protected]

Benefits:

Professional appearance
Not tied to Proton (can migrate to another provider later)
Unlimited aliases (every address at your domain forwards)

PGP with Proton Mail

Proton supports PGP for emailing other PGP users:

Exchange public keys with recipient
Import their key into Proton
Emails are automatically encrypted end-to-end

We’ll cover PGP in detail in Week 9 (GnuPG).

Self-Hosted Email (Advanced)

For maximum privacy, run your own email server:

Complete control
No third party
Very technical (requires sysadmin skills)

Not recommended for beginners. Proton/Tutanota are excellent middle-grounds.

What’s Next

You now have private, encrypted email with aliasing for compartmentalization. Next week, we’ll secure your network traffic with VPNs and understand when to use Tor for maximum anonymity.

Week 6 covers VPNs and Tor—when to use each, and how to set them up.

Summary

This week you:

Learned why Gmail is surveillance
Chose between Proton Mail and Tutanota
Set up encrypted email with 2FA
Created email aliases with SimpleLogin
Started migrating accounts off Gmail
Learned email privacy best practices

Your email is now end-to-end encrypted, and your identity is compartmentalized across aliases. Combined with your hardened browser (Week 3) and password manager (Week 4), you’re building a solid privacy foundation.

← Back to Week 4: Password Managers

Continue to Week 6: VPNs and Tor →

Email Privacy#

The Email Privacy Problem#

Gmail Is Surveillance#

Email Address as Identity#

Part 1: Choosing a Private Email Provider#

Proton Mail (Recommended)#

Tutanota#

Decision Guide#

Part 2: Setting Up Proton Mail#

Create Your Account#

Initial Setup#

Understanding Proton Mail’s Encryption#

Part 3: Email Aliases for Compartmentalization#

Why Aliases Matter#

Alias Services: SimpleLogin vs AnonAddy#

Part 4: Setting Up SimpleLogin#

Create SimpleLogin Account#

Create Your First Alias#

Alias Naming Strategy#

Browser Extension for Quick Aliases#

Replying Through Aliases#

Disabling Aliases#

Part 5: Migrating from Gmail#

Phase 1: New Accounts Use Proton + Aliases#

Phase 2: Migrate Critical Accounts#

Phase 3: Forward Gmail to Proton#

Phase 4: Monitor and Sunset Gmail#

Part 6: Email Best Practices#

Send Encrypted Emails to Non-Proton Users#

Avoid Email for Sensitive Communications#

Unsubscribe from Everything#

Check for Email in Data Breaches#

Part 7: Mobile Email Setup#

Android#

iOS#

Mobile Tips#

Privacy Checkpoint#

Troubleshooting#

Proton Mail isn’t receiving emails#

SimpleLogin alias not forwarding#

I forgot my Proton Mail password#

Sites reject my alias#

Gmail forwarding stopped working#

Going Further (Optional)#

Custom Domain with Proton#

PGP with Proton Mail#

Self-Hosted Email (Advanced)#

What’s Next#

Summary#