Protect Your Privacy With Cloak

In today's world, most of our important business tasks are done online. To aid our culture's desire for making connectivity as ubiquitous as water, there are signs everywhere boasting free Wi-Fi for patrons of places ranging from restaurants to bowling alleys.

As someone who does a decent amount of their work on evenings and weekends, I find myself frequenting coffeehouses (particularly Starbucks) at least 4-5 times per week. What their Wi-Fi offers me in convenience, I trade off in privacy, since all of the access points at the locations I visit are controlled by Google. The hotspots aren't protected by a password to encrypt data to and from the hotspot, and my computer is visible on the network to any other user.

Since a majority of my free time is spent either blogging, managing my finances or doing work for FDW clients, I'm particularly keen on privacy for the data I transmit over public Wi-Fi. It is way too easy for someone to obtain even a segment of this data, which may contain sensitive information like passwords (at the very least!).

I recently found Cloak, a company that promises to make surfing the Internet on public Wi-Fi safe and easy. Any time I see offers like this, I am skeptical, since I'm a huge fan of rolling my own solution for a particular service like email, instant messaging, etc. However, since getting the functionality of a VPN can be a bit difficult for even though well endowed with the knowledge of technology, I decided to give Cloak a try.

The first thing you'll notice about Cloak is that the software was developed with mobility in mind. You can get Cloak for your Mac laptop, desktop or any iOS device so you're protected no matter which device you choose to use. We'll look at how Cloak works on each of the devices it supports.


The first thing you'll notice after launching Cloak for Mac is that it's very unobtrusive. Access to the software's options are packed into a taskbar icon. Clicking on the icon will give you a screen that displays the current status of your Wi-Fi connection. Here's a typical status screen:

Giving a tap on the Secure my connection button will start the connection process to one of many of Cloak's tunneling servers, which is where the real value starts to be realized.

Using your laptop in different locations around the country can put a strain on most single-site VPN connections. Most VPNs offer one single point of entry for traffic in the country, usually out of a need for security (the less points of entry into a particular network, the more secure it is). Cloak offers several remote access sites to be used based on your location. Say you're traveling to San Francisco on business, but you live on the east coast. You might normally connect to Cloak's East Coast servers, however, that might slow you down when traveling on the other side of the country. Fortunately, the software has an option for auto-sensing which is the fastest available and will automatically connect you to those servers. Traveling out of the country, there are also global options for servers in France, Germany, the Netherlands, and even Japan and Australia, among others.

One of the best features I've found with Cloak is the ability to have your VPN connection available whenever you need it and start automatically on an insecure network. The technical term for this is called VPN on-demand. It works by the use of a whitelist in the Cloak software which establishes a basic rule of "if a network name isn't in this list, automatically connect to the Cloak VPN server of my choosing." It's a feature I enjoy when I just want to get to a coffeeshop and get down to work, eliminating one more barrier I have to complete when trying to get connected.

Of course, the list of pre-approved wireless networks is a snap to set up. On the Mac, it's as easy as clicking the + button and typing in the name of the SSID you want the software to recognize as secure (like a home network).

After you've connected to a network, you'll get one of the following screens:

The window in green indicates you're on a wireless network you've pre-chosen as secure and the Cloak software is smart enough to realize it doesn't need any additional security. However, for ease of use, the Secure my connection button is available just in case.


The process by which Cloak works on an iOS device is the same underneath, although for obvious reason, the screens do look a bit different.

One of the awesome things about Cloak is that if you add a network in your whitelist on the Mac, that information will save to your account and transfer to your iOS device. Cloak operates by using the Certificates storage built into iOS. Each time you update the whitelist, it will download a new group of settings to this store, ensuring you're using the same settings cross-device.

Service Plans

When you first sign up for the service, you'll get a complementary trial of the service, good for a 30-day period. If you wish to continue with a paid plan, multiple options are available:

  • 30 day pass of 5GB data shared between devices for $2.99
  • 7 day pass of unlimited data for $3.99
  • 30 day pass of unlimited data for $9.99
  • 1 year pass of unlimited data for $99.99

The 5GB plan/$2.99 plan seems to be a sort of "Internet special" as it's only available via their website.

A 20% discount is available by sharing a tweet each month that mentions @GetCloak. After they see your tweet, they'll apply the discount.

Final Thoughts

I absolutely love that this kind of security is available for the Mac, designed in a way that blends in with the interface of the device you're using. Where Cloak excels is in the way it makes security both functional and easy to use. It takes the hassle out of making a connection safe from prying eyes. Perhaps the developers of Cloak can do something for the burgeoning market of two-factor authentication, making it just as effortless to use.

That would be absolutely amazing.

  • Pros: easy of use, on-demand connection option for networks not in the whitelist, affordable paid plans, solidy functionality in OS X Yosemite.
  • Cons: downloading a new profile when changes to the whitelist occur on iOS can be a bit annoying.