Hide My Email: An Update to My Digital Privacy Practice

It’s been more than 4 years since I wrote Building Moats Around Data, so, so much has changed since then. It reminded me of a quote by Bill Gates: “Most people overestimate what they can do in one year and underestimate what they can do in ten years.” If anything, the last 4 years have proven this to be the case for our society as well.

In the article above, I wrote:

The first question led me to reading up on the “I have nothing to hide” argument and its implication on privacy development. It’s about the subtle nuance of agency: “I have nothing to hide” is fundamentally different from “I have nothing I want to show you.” The former implies that a person has no reason to not expose everything unless there’s something nefarious going on, shifting the agency of data control to a non-owner. The latter rightfully associates the agency of data control to its owner, implying that sharing is a willful action, not an expectation. If we’re talking about privacy as a right, each citizen should be able to decide what to share, not whether to hide. The nothing-to-hide argument short-circuits that logic to halt critical thinking around privacy and stifle public discussion.

My thinking around data protection stems from this distinction: I am the owner of my data and I should give explicit permission for the harvesting and use of my data. By not protecting my data, I lose my ability to control it, and relinquish that power to someone else.

My thinking on this hasn’t changed a bit. What changed, however, are the new technologies available to help me implement something other than the clumsy six-email system that I used.

In my previous framework, I classified all apps and services I used into 6 categories based on their exposure of my PII (Personally Identifiable Information). I gave each service their own email address in ProtonMail and a “+” alias. This would insulate me from data leaks being used to serial-attack other services sharing the same PII.

However, this approach had several flaws. Aside from the simplistic aliasing scheme that’s easily reverse engineered, the biggest one was inconvenience: I had to think about classification and aliasing every time I sign up for something. If I wanted to shut down communication from a service, I had to manually block its sender address or request account deletion. Keeping track of 6 email addresses and all of their aliases were getting tiring. Occasionally, some services also didn’t support the “+” symbol for archaic reasons.

Random Email Generator

The centerpiece of my current setup is a new iCloud feature awkwardly called: Hide My Email. Essentially, this is an email generation tool that routes incoming emails to an inbox of your choice, and replies are made to appear from the same anonymized address to the recipients as well. Combined with iCloud Keychain, it’s a complete system to manage anonymized emails and randomly generated passwords.

I love the simplicity and effectiveness of this system, despite its UI shortcomings:

  1. It’s significantly more convenient: one tap to generate a new email address the moment a form asks you for one.
  2. It’s more maintainable: the system automatically recommends inactive email addresses for deletion.
  3. It’s private: completely random yet human-readable email addresses (e.g. byte.flicker.0@icloud.com) that is practically impossible to reverse engineer.
  4. It’s integrated and portable: I can reply to messages routed via this address without revealing my real email, as well as having all of them forwarded to a third party email client if I don’t want to use iCloud Mail.

The great thing? There are non-Apple alternatives as well:

  • DuckDuckGo offers a similar service with tracker removal and random email address generation
  • 1Password and Fastmail partnered up to offer a password manager + randomized email generation service closest to Apple’s integrated offering.

Hide My Email has completely replaced my need for a manual solution. Until passwords and login emails are rendered obsolete in the future, this is probably one of the best intermediate solutions there is.

Leave a Reply

Your email address will not be published. Required fields are marked *