How I tried to buy something totally anonymously online

My experiences with trying to buy something online without revealing anything about my identity, and why this is so difficult.

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Privacy is important. Don’t let anyone tell you otherwise.

Keeping your personal information, well, personal, is all but impossible these days.

I’ve been looking into buying a VPN service for a long time now. A VPN helps ensure privacy when I browse online, and also helps prevent people in the coffee shop from being able to steal personally identifying information from me while I’m there (which is stupidly easy to do).

I finally decided to take the plunge and do it recently. I found a good deal on a service (I chose NordVPN, if you must know) and the price was right.

However, if the whole purpose of a VPN is privacy (and hopefully anonymity), then just paying with my debit card or PayPal or similar service wouldn’t make much sense. If I want to be able to be online without anyone knowing it, I should be able to pay online without anyone knowing it.

And so, I went down the rabbit hole, or ate the purple pill (I haven’t seen The Matrix, so I tend to get the colors wrong), or however you call it. I decided to try and sign up for a VPN service without giving any personally identifying information.

Read on to see how I did.

Anonymous payment

The first issue is: how would I pay for it?

After some research, I decided on using a prepaid debit card. You can buy these at your average convenience store, and some of them don’t require any personally identifying information to load money on them. You can pay for them with cash. This is exactly what I did.

I went with the OneVanilla Visa card. It has been around for a while, and has a reasonable track record. Plus, it is specifically designed to help you purchase online.

I went to my local Walgreens, picked out a suitable card, and paid enough money to purchase my VPN service (plus a $5.95 fee for the card) and I was on my way out the door in minutes.

I have to admit that this was a little nerve wracking. I mean, what if I did this wrong and my money got locked in somehow? I had never bought a prepaid debit card before, at least one that wasn’t for a particular store.

The things I do in order to share my experiences with you, dear readers.

The OneVanilla card is designed for online shopping. You can enter a ZIP code (it can be any ZIP code) and you set a PIN during the first transaction. It’s almost as if they know that you want to be anonymous, and are okay with it.

Anonymous email address

The VPN requires an email address for sending out account updates and password resets. But it wouldn’t make sense to have anonymous payment and then just use my Gmail account for the service!

So I needed to find an anonymous email address, one that I could access normally, but wouldn’t be linked to my personal information at all.

I own a bunch of domains, and could create whateverIwant@empathicfinance.com, for example, but any domain I own is linked to me in some way. So I needed to look elsewhere.

There are a lot of services out that that offer anonymous email. I was particularly taken with Slippery Email, which creates an email address just by clicking a button. The URL to the page is your password, and the whole thing expires in 8 days.

But I didn’t want an email that expired. I wanted it to be anonymous, but persistent.

I eventually found this in ProtonMail, an email service based in Switzerland (a place which knows a thing or two about privacy) that requires no personal identifying information in order to register. You don’t even need to give a recovery email account. This is kind of dangerous, as if I were to lose my password I’d have no recourse, but that’s the risk one runs when trying to cover one’s tracks.

I signed up.

Anonymous location

You can’t sign up for a privacy service from your home. That would be silly.

So when I went to go sign up, I went to a public location, the exact kind of location where I would be using the service.

Anonymous fail

And then I signed up for the service. I entered my card information, a fake name (because why not?) and used the ZIP code I had linked to the card. I also signed up under my new anonymous email account.

And then the moment of truth:

No matter how many times I tried, I could not get the payment to go through. Gulp. What had I got myself into?

Anonymous (?) customer service

Eventually, I got stuck. And then I shrugged and did the unthinkable: I clicked the “Chat Now” button on the website.

And so a few minutes later, I was chatting with Max, a patient and knowledgeable customer service associate.

It was pretty surreal to be chatting with customer service about trying to undertake an anonymous transaction, I know. But what else could I do?

We tried the usual tricks (using a different browser, turning off incognito mode, etc.) before eventually settling in on the culprit: “Does your card allow for payments to international destinations?”

I looked at the card, it big block letters, the card said “VALID ONLY IN THE UNITED STATES.”

Damn.

He suggested paying in Bitcoin, which was a whole other set of complications. And he was nice enough to give me a 3-day trial, so I could test out the service. I thanked him, and we went our various ways.

Anonymous and unsuccessful

So after all that, I have a gift card but no VPN service. And I have not been able to find any payment method that is both anonymous and international. This means that I either just pay for the service in my usual manner, forgetting about anonymity, or find a different VPN service, or, well, I don’t know what.

The point being, it is incredibly hard to be anonymous and purchase things online. For most people, it’s not worth the hassle.

But is that the best we can do as a society? Wouldn’t it better if we were to strive for a system where we controlled our information and our payment records? I don’t want anyone to know I’m signing up for a VPN serv…whoops.

But enough about me. How do you purchase things online and stay anonymous? How could I have done this differently? I’d love to hear about it in the comments below.

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