IF YOU’RE LIKE me, one of the first things you do in the morning is check your email. And, if you’re like me, you also wonder who else has read your email. That’s not a paranoid concern. If you use a web-based email service such as Gmail or Outlook 365, the answer is kind of obvious and frightening.
Even if you delete an email the moment you read it on your computer or mobile phone, that doesn’t necessarily erase the content. There’s still a copy of it somewhere. Web mail is cloud-based, so in order to be able to access it from any device anywhere, at any time, there have to be redundant copies. If you use Gmail, for example, a copy of every email sent and received through your Gmail account is retained on various servers worldwide at Google. This is also true if you use email systems provided by Yahoo, Apple, AT&T, Comcast, Microsoft, or even your workplace. Any emails you send can also be inspected, at any time, by the hosting company. Allegedly this is to filter out malware, but the reality is that third parties can and do access our emails for other, more sinister and self-serving, reasons.
While most of us may tolerate having our emails scanned for malware, and perhaps some of us tolerate scanning for advertising purposes, the idea of third parties reading our correspondence and acting on specific contents found within specific emails is downright disturbing.
The least you can do is make it much harder for them to do so.
Start With Encryption
Most web-based email services use encryption when the email is in transit. However, when some services transmit mail between Mail Transfer Agents (MTAs), they may not be using encryption, thus your message is in the open. To become invisible you will need to encrypt your messages.
Most email encryption uses what’s called asymmetrical encryption. That means I generate two keys: a private key that stays on my device, which I never share, and a public key that I post freely on the internet. The two keys are different yet mathematically related.
So how would encrypting the contents of your email work?
The most popular method of email encryption is PGP, which stands for “Pretty Good Privacy.” It is not free. It is a product of the Symantec Corporation. But its creator, Phil Zimmermann, also authored an open-source version, OpenPGP, which is free. And a third option, GPG (GNU Privacy Guard), created by Werner Koch, is also free. The good news is that all three are interoperational. That means that no matter which version of PGP you use, the basic functions are the same.
When Edward Snowden first decided to disclose the sensitive data he’d copied from the NSA, he needed the assistance of like-minded people scattered around the world. Privacy advocate and filmmaker Laura Poitras had recently finished a documentary about the lives of whistle-blowers. Snowden wanted to establish an encrypted exchange with Poitras, except only a few people knew her public key.
Snowden reached out to Micah Lee of the Electronic Frontier Foundation. Lee’s public key was available online and, according to the account published on the Intercept, he had Poitras’s public key. Lee checked to see if Poitras would permit him to share it. She would.
How would they know each other’s new email addresses? In other words, if both parties were totally anonymous, how would they know who was who and whom they could trust? How could Snowden, for example, rule out the possibility that the NSA or someone else wasn’t posing as Poitras’s new email account? Public keys are long, so you can’t just pick up a secure phone and read out the characters to the other person. You need a secure email exchange.
By enlisting Lee once again, both Snowden and Poitras could anchor their trust in someone when setting up their new and anonymous email accounts. Poitras first shared her new public key with Lee. Lee did not use the actual key but instead a 40-character abbreviation (or a fingerprint) of Poitras’s public key. This he posted to a public site—Twitter.
Sometimes in order to become invisible you have to use the visible.
Snowden finally sent Poitras an encrypted e‑mail identifying himself only as “Citizenfour.” This signature became the title of her Academy Award–winning documentary about his privacy rights campaign.
That might seem like the end—now they could communicate securely via encrypted e‑mail—but it wasn’t. It was just the beginning.
Picking an Encryption Service
Both the strength of the mathematical operation and the length of the encryption key determine how easy it is for someone without a key to crack your code.
Encryption algorithms in use today are public. You want that. Public algorithms have been vetted for weakness—meaning people have been purposely trying to break them. Whenever one of the public algorithms becomes weak or is cracked, it is retired, and newer, stronger algorithms are used instead.
The keys are (more or less) under your control, and so, as you might guess, their management is very important. If you generate an encryption key, you—and no one else—will have the key stored on your device. If you let a company perform the encryption, say, in the cloud, then that company might also keep the key after he or she shares it with you and may also be compelled by court order to share the key with law enforcement or a government agency, with or without a warrant.
When you encrypt a message—an e‑mail, text, or phone call—use end‑to‑end encryption. That means your message stays unreadable until it reaches its intended recipient. With end‑to‑end encryption, only you and your recipient have the keys to decode the message. Not the telecommunications carrier, website owner, or app developer—the parties that law enforcement or government will ask to turn over information about you. Do a Google search for “end‑to‑end encryption voice call.” If the app or service doesn’t use end-to-end encryption, then choose another.
If all this sounds complicated, that’s because it is. But there are PGP plug-ins for the Chrome and Firefox Internet browsers that make encryption easier. One is Mailvelope, which neatly handles the public and private encryption keys of PGP. Simply type in a passphrase, which will be used to generate the public and private keys. Then whenever you write a web-based email, select a recipient, and if the recipient has a public key available, you will then have the option to send that person an encrypted message.
Beyond Encryption: Metadata
Even if you encrypt your e‑mail messages with PGP, a small but information-rich part of your message is still readable by just about anyone. In defending itself from the Snowden revelations, the US government stated repeatedly that it doesn’t capture the actual contents of our emails, which in this case would be unreadable with PGP encryption. Instead, the government said it collects only the email’s metadata.
You’d be surprised by how much can be learned from the email path and the frequency of emails alone.
What is email metadata? It is the information in the To and From fields as well as the IP addresses of the various servers that handle the email from origin to recipient. It also includes the subject line, which can sometimes be very revealing as to the encrypted contents of the message. Metadata, a legacy from the early days of the internet, is still included on every email sent and received, but modern email readers hide this information from display.
That might sound okay, since the third parties are not actually reading the content, and you probably don’t care about the mechanics of how those emails traveled—the various server addresses and the time stamps—but you’d be surprised by how much can be learned from the email path and the frequency of emails alone.
According to Snowden, our email, text, and phone metadata is being collected by the NSA and other agencies. But the government can’t collect metadata from everyone—or can it? Technically, no. However, there’s been a sharp rise in “legal” collection since 2001.
To become truly invisible in the digital world you will need to do more than encrypt your messages. You will need to:
To start, your IP address reveals where you are in the world, what provider you use, and the identity of the person paying for the internet service (which may or may not be you). All these pieces of information are included within the email metadata and can later be used to identify you uniquely. Any communication, whether it’s email or not, can be used to identify you based on the Internal Protocol (IP) address that’s assigned to the router you are using while you are at home, work, or a friend’s place.
IP addresses in emails can of course be forged. Someone might use a proxy address—not his or her real IP address but someone else’s—that an email appears to originate from another location. A proxy is like a foreign-language translator—you speak to the translator, and the translator speaks to the foreign-language speaker—only the message remains exactly the same. The point here is that someone might use a proxy from China or even Germany to evade detection on an email that really comes from North Korea.
Instead of hosting your own proxy, you can use a service known as an anonymous remailer, which will mask your email’s IP address for you. An anonymous remailer simply changes the email address of the sender before sending the message to its intended recipient. The recipient can respond via the remailer. That’s the simplest version.
One way to mask your IP address is to use the onion router (Tor), which is what Snowden and Poitras did. Tor is designed to be used by people living in harsh regimes as a way to avoid censorship of popular media and services and to prevent anyone from tracking what search terms they use. Tor remains free and can be used by anyone, anywhere—even you.
How does Tor work? It upends the usual model for accessing a website. When you use Tor, the direct line between you and your target website is obscured by additional nodes, and every ten seconds the chain of nodes connecting you to whatever site you are looking at changes without disruption to you. The various nodes that connect you to a site are like layers within an onion. In other words, if someone were to backtrack from the destination website and try to find you, they’d be unable to because the path would be constantly changing. Unless your entry point and your exit point become associated somehow, your connection is considered anonymous.
To use Tor you will need the modified Firefox browser from the Tor site (torproject.org). Always look for legitimate Tor browsers for your operating system from the Tor project website. Do not use a third-party site. For Android operating systems, Orbot is a legitimate free Tor app from Google Play that both encrypts your traffic and obscures your IP address. On iOS devices (iPad, iPhone), install the Onion Browser, a legitimate app from the iTunes app store.
It should be noted, however, that there are several weaknesses with Tor: You have no control over the exit nodes, which may be under the control of government or law enforcement; you can still be profiled and possibly identified; and Tor is very slow.
That being said, if you still decide to use Tor you should not run it in the same physical device that you use for browsing. In other words, have a laptop for browsing the web and a separate device for Tor (for instance, a Raspberry Pi minicomputer running Tor software). The idea here is that if somebody is able to compromise your laptop they still won’t be able to peel off your Tor transport layer as it is running on a separate physical box.
Create a new (invisible) account
Legacy email accounts might be connected in various ways to other parts of your life—friends, hobbies, work. To communicate in secrecy, you will need to create new email accounts using Tor so that the IP address setting up the account is not associated with your real identity in any way.
Creating anonymous email addresses is challenging but possible.
Since you will leave a trail if you pay for private email services, you’re actually better off using a free web service. A minor hassle: Gmail, Microsoft, Yahoo, and others require you to supply a phone number to verify your identify. Obviously you can’t use your real cellphone number, since it may be connected to your real name and real address. You might be able to set up a Skype phone number if it supports voice authentication instead of SMS authentication; however, you will still need an existing email account and a prepaid gift card to set it up.
However, purchasing a burner phone anonymously will be tricky. Sure, I could walk into Walmart and pay cash for a burner phone and one hundred minutes of airtime. Who would know? Well, lots of people would.
First, how did I get to Walmart? Did I take an Uber car? Did I take a taxi? These records can all be subpoenaed. I could drive my own car, but law enforcement uses automatic license plate recognition technology (ALPR) in large public parking lots to look for missing and stolen vehicles as well as people on whom there are outstanding warrants. The ALPR records can be subpoenaed.
Creating anonymous email addresses is challenging but possible.
Even if I walked to Walmart, once I entered the store my face would be visible on several security cameras within the store itself, and that video can be subpoenaed.
Okay, so let’s say I send a stranger to the store—maybe a homeless person I hired on the spot. That person walks in and buys the phone and several data refill cards with cash. Maybe you arrange to meet this person later away from the store. This would help physically distance yourself from the actual transaction.
Activation of the prepaid phone requires either calling the mobile operator’s customer service department or activating it on the provider’s website. To avoid being recorded for “quality assurance,” it’s safer to activate over the web. Using Tor over an open wireless network after you’ve changed your MAC address should be the minimum safeguards. You should make up all the subscriber information you enter on the website. For your address, just Google the address of a major hotel and use that. Make up a birth date and PIN that you’ll remember in case you need to contact customer service in the future.
After using Tor to randomize your IP address, and after creating a Gmail account that has nothing to do with your real phone number, Google sends your phone a verification code or a voice call. Now you have a Gmail account that is virtually untraceable. We can produce reasonably secure emails whose IP address—thanks to Tor—is anonymous (although you don’t have control over the exit nodes) and whose contents, thanks to PGP, can’t be read except by the intended recipient.
As you can see, becoming invisible and keeping yourself invisible require tremendous discipline and perpetual diligence. But it is worth it. The most important takeaways are: First, be aware of all the ways that someone can identify you even if you undertake some but not all of the precautions I’ve described. And if you do undertake all these precautions, know that you need to perform due diligence every time you use your anonymous accounts. No exceptions.