A Few Ideas About Staying Safe and Anonymous Online

My daughter sent me an email last night asking me if an app called Disconnect might work to help keep her safe online, especially since she has experienced her virtual private network (VPN) connection slowing down her online activity.

Here is some of what I emailed to her and thought I’d expand it a bit and post it as it might help you too.

A VPN’s encrypted tunnel does have overhead so it will slow down your internet connection. No way around that and there are always trade-offs like this in order to have good security. A VPN’s encrypted “tunnel” through your internet connection — for your traffic to travel through — typically requires using 10-15% of your internet connection’s bandwidth, but it’s worth it almost all of the time.

One tradeoff many of us make is using good, hard to remember, and always different passwords for every website and app we use. Doing so is very challenging as is keeping track of them (which is why using a password manager like LastPass is so important).

That Disconnect app is just a tracking blocker, but it does offer a VPN in their Premium version for both blocking trackers and keeping traffic encrypted and somewhat anonymous (and it’s good to see that Disconnect does not keep logs of your VPN traffic and use). Disconnect’s VPN will slow down your internet connection just like any VPN does, but I haven’t done a side-by-side comparison between Disconnect’s VPN and the one we use.

Our chosen VPN is Private Internet Access (PIA), a provider that also keeps no logs and has 3,194 servers in 36 locations across 24 countries. Our entire family (and our business) uses PIA. Unless one uses the Disconnect Premium with their built-in VPN, your ISP and trackers can still know where you go and what your iPhone’s apps do (i.e., websites you visit; connections your phone makes through apps; etc.).

My preference is to use best-in-class tracking blockers and a VPN, but want to keep them separate (e.g., Disconnect’s Premium product is $5 per month or $50 per year  for only 3 devices while PIA’s is $6.95 per month or $39.95 for a year but they allow up to 5 devices).

Just know that, even with all of the measures I’m going to outline below, you always, always want to use a VPN when you connect to public Wifi (as well as a few other things) regardless of whether you are only concerned about being tracked while online.

Also, understand that there isn’t anything that is 100% foolproof. Cyber security is an “arms race” and as the good guys build better defenses, the bad guys are building better hacking/cracking and tracking tools. For example, the tech news site Ars Technica had this comprehensive article about how sites can still fingerprint you online even when you use multiple browsers so do your best to stay untracked and anonymous as you can.

What you use all depends upon what you want to achieve:

  • Hide and encrypt all traffic (from browsers and apps) on your computer, phone or tablet? A VPN is your only solution.
  • Don’t want your web browser traffic tracked? There are apps like Disconnect that kinda, sorta, do OK (there are still ways to track you based on IP address; browser and device type; etc.). Here are some apps that will help you to not be tracked:
  • Be completely anonymous? Then you want to use Tor (see “ANONYMOUS WEB SURFING” below) while taking in to consideration their cautions (also see “FURTHER READING” below on ways to stay anonymous using Tor).

Tor is free software and an open network that helps you defend against traffic analysis, a form of network surveillance that threatens personal freedom and privacy, confidential business activities and relationships, and state security.

Use DuckDuckGo.com for your searches. They keep no logs or search history. Make sure you use it in a “clean” browser.

Speaking of clean browsers, consider using site-specific browsers for those apps you don’t want tracking you (like Facebook!) all over the web.

I never login to Facebook (and other web apps like it) in ANY of my main web browsers since Facebook is notorious for tracking. Instead I use Fluid App for the Mac to create a site-specific browser that uses the same “engine” (WebKit) that Safari uses and you can create a web browser app which is essentially a Safari browser.

It works quite well and I have a couple of dozen site-specific browsers for my key clients so I can have their Google Suite apps, websites, web apps like Salesforce or Mailchimp, all open running in that client’s site-specific browser.

In that way I can, for example, use Facebook all day long but it cannot track my general browsing habits.

Only you can decide if the VPN trade-off in speed is worth it. It is for me and, frankly, I do not see it being any kind of an issue related to speed.

I use the Google Chrome browser Private Internet Access (PIA) extension since Chrome is my main browser on my Mac. As such all of my Chrome traffic is sent through PIA’s encrypted tunnel. But since my Mac itself is not connected via VPN, I can open Safari or Firefox and access sites, upload photos or videos, download stock imagery, and other tasks all at my full internet-connection speeds whenever I need to do so.

If I want to be anonymous (though read their safety precautions on the Tor Project website) I open Tor browser on my Mac (not through the PIA VPN) and it’s somewhat slow, but fast enough.

If I want to be tinfoil hat safe — you know, to keep out the gamma rays and government brain-spying (I’m kidding) — there are more geeky ways to make certain my Mac cannot be compromised nor any trace left on it. When doing so I do one of two things:

1) Use Parallels on my Mac and launch an Ubuntu Linux virtual machine running the Tor browser. When I open up that virtual machine, I have it set to automatically connect to PIA so I can freely use anything on that “separate machine” knowing that my main Mac cannot get compromised. (NOTE: When I first set this up I also made a copy of this virtual machine. So if I am using it an inadvertently stumble across something I suspect has installed malware on my “Ubuntu Linux-run computer”, I just throw away that virtual machine instance and copy another one from my backup drive.

NOTE: So in this case I am using using Tor over a VPN which is adding yet another layer of security and anonymity.

2) Run Tails (The Amnesiac Incognito Live System) is a live operating system that you can start on almost any computer from a DVD, USB stick, or SD card which helps you to:

  • use the Internet anonymously and circumvent censorship; all connections to the Internet are forced to go through the Tor network;
  • leave no trace on the computer you are using unless you ask it to do so explicitly;
  • use state-of-the-art cryptographic tools to encrypt your files, emails and instant messaging.

I have a thumb drive with Tails installed which I can use to boot from on most computers. So if traveling overseas one could use Tails to ensure there wasn’t any trace left on one’s own computer. Tails is especially important for people in countries where all internet traffic is tracked and censored, or if someone is a whistleblower or journalist that could be compromised if identified.


Hope this helps. Stay safe out there.

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About Steve Borsch

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Podcasting hit the mainstream in July of 2005 when Apple added podcast show support within iTunes. I'd seen this coming so started podcasting in May of 2005 and kept going until August of 2007. Unfortunately was never 'discovered' by national broadcasters, but made a delightfully large number of connections with people all over the world because of these shows. Click here to view the archive of my podcast posts.