001 - Refining the Email Strategy of the GOAT

Update May 3, 2026

I received valuable feedback from a reader (thank you 🙏) and want to clarify an important point in the original post's decision tree for email alias usage:

In the hierarchy of options when an email alias is blocked, dummy Gmail/Yahoo/Outlook accounts should be your absolute last resort. Before reaching that point, I recommend creating a free Proton or Tuta email account (signing up with no personally identifiable information). These appear as legitimate email addresses when signing up for services that don't accept your alias.

If your Proton or Tuta account is still rejected (rare but possible), you'll need to decide whether using a mainstream provider's dummy account is worth it.

Remember: if this service is not absolutely necessary, you always have the option to not use it at all. Maybe there's a privacy-friendly alternative!

Introduction

Privacy‑savvy readers of Michael Bazzell’s Extreme Privacy (5th Edition) know that email is the digital front door to our lives. A single address can betray more than a careless “reply‑all” ever could. Yet the modern toolbox—custom domains, aliasing services such as SimpleLogin, and the ever‑reliable ProtonMail—offers enough levers to keep the door firmly shut.

In this post we’ll walk through a decision tree that helps you pick the right combination of real‑name, pseudonym, and throwaway addresses for any scenario, while sprinkling in a dash of clever wordplay (because even privacy geeks deserve a chuckle).

1. The Core Principle: “Know Your Alias”

Before diving into the tree, remember the golden rule: Anything that reveals your true identity can be linked back to you. Whether you’re signing up for Netflix, a newsletter, or a government portal, the email you hand over becomes a breadcrumb trail. The goal is to control where those crumbs land.

2. Decision Tree Overview

Below is a textual decision tree that you can copy‑paste into a diagramming tool (or simply follow in your head). Each branch ends with a recommended email setup.

Please skip to the next section 2.1 if you've tried an alias but it has been blocked.

Start
 ├─► Are you using your real name?
 │        └─► Yes → Use a custom domain with your real name on ProtonMail.
 │               (e.g., john.doe@mydomain.com) – keeps branding clean and
 │                encrypted end‑to‑end.
 │
 ├─► No – Are you using a pseudo name or initials?
 │        └─► Yes → Register a generic custom domain (e.g., mymail.io)
 │               and route aliases through SimpleLogin.
 │               Example: jd@mymail.io → forwards to john.doe@proton.me.
 │
 ├─► No – Are you using a purely fake name?
 │        └─► Yes → Generate a random SimpleLogin address.
 │               Example: zebra123@simplelogin.co → forwards to a Proton mailbox.
 │
 └─► None of the above? → Create a dummy Gmail or Microsoft throwaway account.

2.1. What to Do When an Alias Gets Blocked

3. Step‑by‑Step Implementation

3.1. Set Up a Custom Domain (Real‑Name Path)

1. Purchase a domain (e.g., yourname.dev).
2. Configure DNS to point MX records to ProtonMail or your secured email provider of choice (Tuta, Mailbox, etc).
3. Create the address firstname.lastname@yourname.dev inside Proton.
4. Enable SPF/DKIM for deliverability.

Result: A professional‑looking, encrypted inbox that still carries your real identity—perfect for business contacts, official registrations, and any situation where you must be identifiable.

3.2. Generic Custom Domain + SimpleLogin (Pseudo‑Name Path)

1. Register a short, neutral domain (e.g., mailbox.io).
2. Add it to SimpleLogin as a sender domain.
3. Create aliases like j.doe@mailbox.io that forward to a ProtonMail mailbox.
4. Rotate aliases whenever a service starts flagging them.

Result: You keep the same inbox while presenting a “generic” façade to the outside world.

3.3. Random SimpleLogin Addresses (Fake‑Name Path)

1. In SimpleLogin, click “Generate Random Alias.”
2. Choose a random prefix (e.g., cactus42) and a domain you own or SimpleLogin’s default.
3. Forward the alias to a Proton or Tutanota mailbox.

Result: An address that looks like it was generated by a mischievous AI—great for newsletters, forum sign‑ups, or any site that loves to spam.

3.4. Throwaway Gmail/Microsoft Accounts (Last Resort)

• Create a fresh Gmail or Outlook account with minimal personal data.
• Use it only for services that explicitly block your other aliases.

Result: A disposable mailbox that can be abandoned without affecting your primary identity.

4. Practical Tips & Wordplay

• “Alias‑ing” the problem: Think of each alias as a disguise for your inbox—James Bond never shows up as himself at a casino.
• “Spam‑tastic” protection: Rotate aliases every 30–60 days; spam filters love fresh faces.
• “Domain‑inate” your brand: Even if you’re using a pseudonym, a tidy custom domain looks far less suspicious than a free‑service address.

5. Summary Checklist

• Real name? → Custom domain on Proton or Tuta.
• Pseudo name/initials? → Generic custom domain + SimpleLogin.
• Fake name? → Random SimpleLogin address.
• Blocked? → Try generic domain → Make a free Proton/Tuta account (no PII) → Add Proton alias or upgrade to Tuta.
• All else fails? → Throwaway Gmail/Microsoft.

Keep this checklist handy, and you’ll never be caught off‑guard by a privacy‑draining sign‑up form again.

6. Beyond Proton and SimpleLogin

While ProtonMail and SimpleLogin make excellent starring roles in our privacy play, they are by no means the only actors on the stage. The privacy‑and‑security landscape evolves faster than a phishing email during a holiday sale, and new tools surface regularly.

For the most up‑to‑date recommendations—whether you’re hunting for a fresh aliasing service, a hardened mail provider, or a complete privacy suite—I rely on https://www.privacyguides.org/. Their curated, community‑vetted lists keep pace with emerging threats and innovations, ensuring you can always choose the best‑fit solution for your threat model.

Closing Thought

As Michael Bazzell reminds us, privacy is a habit, not a one‑off configuration. By treating each email address as a carefully chosen mask, you stay one step ahead of trackers, spammers, and the occasional nosy data broker.

Happy masking, and may your inbox stay as pristine as a freshly‑wiped slate!