A reader recently asked me how they could use aliases in Outlook.com to create an anonymous email account. My answer was simple: you really can't.
Microsoft's implementation of aliases is not designed to hide your identity. Instead, Outlook.com aliases are about creating throw away addresses that you can give out to marketers and others to avoid plugging up your inbox.
But the question remains, how do you create an anonymous email account? Let's take a look.
Note: This tutorial is not meant for someone in an oppressive country looking to hide themselves from government interlopers. This is aimed at people who want anonymity, but the stakes if they're found out aren't at risk of death or imprisonment.
Also keep in mind that no system is foolproof. But for most people, the instructions below should be good enough.
It all starts with Tor
Before we get to creating an anonymous email account we have to make sure our location and Internet Protocol address (IP) are also anonymous. Not everyone may want to take this step. Let's say all you want to do is use a pen name to submit letters to the editor at a national newspaper. Depending on your situation, you may not really care about hiding your location under this scenario. Not masking your location means that a motivated person will probably be able to find you.
The easiest way to hide your location is to download the Tor (The Onion Router) Browser, which is based on Firefox. Tor reroutes you through a series of servers, dubbed nodes, supplied by volunteers. By the time you exit the server network onto the open Internet it is very difficult to figure out where you came from.
The Tor Browser is just like any other browser. The only difference is it takes a few extra seconds to start-up as the browser connects to the Tor network.
You can download the Tor Browser directly from the Tor project's website and then install it. When you install the browser you end up with a folder that contains the program, which is usually installed to your desktop.
The Tor Browser isn't integrated into your system the way other apps are. If you really want to go anonymous, I would recommend moving the folder to a USB drive and running it off that.
Now it's time to get communicating anonymously. One thing you don't want to do is choose a mainstream service like Gmail, Outlook.com, or Yahoo. These services require a mobile phone number and other identifying information at sign-up, which defeats the entire purpose of an anonymous email account.
Two good options are Hushmail and the Disposable Inbox from VPN provider Hide My Ass. Hushmail has had some issues with privacy. Nevertheless, notable privacy-conscious types such as the Electronic Frontier Foundation and Phil Zimmermann, the creator of PGP encryption, recommend the service.
The solution from Hide My Ass isn't perfect either. At sign-up, for example, the company asks for your real email address so they can notify you when you have new messages. This is not a good idea since having your official account connected to your anonymous account defeats what we're trying to accomplish.
Hide My Ass does not require you to supply your real email so just don't bother to put that in.
A nice feature of Hide My Ass's disposable inbox is that you can set the email address to disappear after 24 hours or up to a year.
Once you've chosen your email provider the key is to use the Tor Browser every time you connect with the service. One slip up and you'll expose a real location you visit--be it your home or a local café.
You should also ensure that any time you connect to your anonymous email you are always doing so via HTTPS. This should happen by default with the two providers mentioned above, but it's still worth double checking.
Creating an anonymous email account takes a bit of work, but the Tor Browser and these two anonymous email providers make it much easier.