How to Surf the Web Anonymously using macOS

This tutorial will guide you in installing, setting up and using Tor in macOS – to help keep your identity completely private and surf the web anonymously.

Background

When some people think of anonymous web browsing, they may assume that only ‘hackers’ and people with poor intentions would be interested in remaining anonymous online. This is simply not true. From the “About Tor” page –

Individuals use Tor to keep websites from tracking them and their family members, or to connect to news sites, instant messaging services, or the like when these are blocked by their local Internet providers. Individuals also use Tor for socially sensitive communication: chat rooms and web forums for rape and abuse survivors, or people with illnesses.

Journalists use Tor to communicate more safely with whistleblowers and dissidents. Non-governmental organizations (NGOs) use Tor to allow their workers to connect to their home website while they’re in a foreign country, without notifying everybody nearby that they’re working with that organization.

Tor works by encrypting your traffic and sending it through three random servers in the Tor network. The last relay sends the traffic out onto the public Internet.

How to Surf the Web Anonymously Using Tor

It should be mentioned up front – when you use Tor, your surfing speed will decrease. This is due to the fact that the Tor network relies on people donating servers – and there aren’t enough servers to keep up with the demand. Tor isn’t meant to be used with file sharing apps or used to download huge files. Patience is the key when using Tor. In addition, not all site will function perfectly when you’re using Tor – particularly if you opt to block javascript (more on this later/farther down in this article).

1. First things first, head over to the Tor download page and download the version for macOS. Installing Tor is as simple as dragging the app to your Applications folder. Open it from there.
2. You’ll be asked to go through a little setup ‘wizard’ the first time you use Tor. If you live in a country that censors Tor (the big three are Egypt, China and Turkey) or are using an Internet connection that requires a proxy, click the Configure button and follow the instructions to setup Tor. Otherwise click the Connect button.
3. Give the Tor browser a moment or two to configure itself and connect to the Tor network. This probably won’t take very long, but it can take several minutes.
4. Once a secure connection has been established the browser will launch. If it looks a bit familiar, you’ve probably used Firefox at some point – that’s the ‘base’ of the Tor browser. A good first site to visit is https://check.torproject.org, which will check your browser to make sure it’s properly connected to the Tor network.
5. You should see a big green Congratulations message.
6. Another good site to visit is https://whatsmyip.com, which will show where websites believe you’re visiting from. As illustrated in the screenshot below, the site thought I was in France (I was not, I was using Tor).
7. Visit one of your favorite sites and then click the i button right next to the ‘lock’ icon at the very beginning of the address bar (see screenshot below). A little ‘popup’ will appear and show you the path/Tor connection that has been established. There will be three locations between you and the site you’ve visiting. Those are the three “circuits” that all of your encrypted traffic will go through before it hits the site you’re visiting, making it extremely secure.
8. If you want to use the absolute maximum amount of security Tor can provide (which isn’t the default setting), click Tor Browser from the menu bar and then Preferences… from the list.
9. Navigate to the Privacy & Security section by selecting it from the column on the left side of the Preferences window. Scroll down to the Security Level section and then select Safest from the list of options. Review the information provided for the Safest option. When using Safest as your level of security on Tor, some sites aren’t going to load properly – some won’t load at all. At that point you’ll need to lower the security level in order to get that site to function properly – which is a personal judgement call only you can make.
10. Another common way to surf web anonymously is to use a VPN in addition to Tor. I use a VPN every single time I connect to the Internet, whether I’m using Tor or not. I strongly recommend (and personally use) PIA as a VPN provider, if you don’t have one yet.
11. Enjoy browsing safely! For more detailed information about Tor, visit the documentation section of their site.