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Cloak VPN for OS X and iOS review

Sections: iDevice Apps, Internet / Websites, iPad, iPad mini, iPhone, iPhone/iPod touch/iPad, iPod touch, Mac Software, Reviews, System Utilities

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Provides: VPN protection for iOS and Mac OS X
Developer: Cloak
Minimum Requirements: OS X 10.7 or above, iOS 4.3 or above
Price: One month free trial; Monthly plans start at $2 for the Mini with 5GB, $8 for the Basic with 25GB, and $15 for the Pro with 60 GB
Availability: Now

Updated 3/26/13 to reflect Cloak’s new pricing announced 3/25/13. Check out full news of the updates here.

A Virtual Private Network (VPN) protects the data you send to and from web pages by rendering it illegible to other users. If your home WiFi network is protected by a password, your data is safely encrypted (scrambled), but when you pull out your MacBook/iPad/iPhone in a coffee shop and join their WiFi, much of the information you send or access is completely visible to other users on that network. Your average user won’t know how to read the information, but a dedicated thief just needs a free program like Wireshark or Firesheep and some patience. If you’re worried about securing your private information, Cloak can help you guarantee your privacy on public WiFi networks.

What Is It?

Most people are familiar with a VPN through work, as corporations can afford the time and expense of setting up a VPN for their employees. Setting up your own VPN can be time consuming and technically challenging, and may be incredibly expensive (I tried to set up my own, only to find out I’d need to upgrade my home Internet service to a business plan as my ISP specifically forbade VPN services on home plans). Cloak has done all the hard work of building a personal VPN; the company’s goal is to create beautiful and easy-to-use software, and both the iOS and Mac OS X versions of Cloak exceed that goal. The company launched v1.0 of Cloak at Macworld this year, and after an extended beta period, the team has delivered apps that are exceptionally simple to use with protection that’s rock solid.

Why Should you Cloak?

Cloak’s service has the advantage of relying on multiple cloud hosting providers like Rackspace and Amazon Web Services, meaning you get resiliency, redundancy, and a speedier connection for a much lower price than you’d pay to provision a VPN yourself. When your Cloak VPN connects it can use your exact location to pinpoint the nearest Cloak server (or an approximation, if you disable Location Services). From there, the service negotiates a secure connection between your device and the Cloak server. Once that’s established, everything you send/receive on that public WiFi network is encrypted and completely invisible to your fellow coffee shop patrons.

To test Cloak, I created an unsecured WiFi network and ran some simple tests to see what my network traffic looked like before and after “cloaking.” Using my trusty copy of Wireshark, I watched the network traffic; with no cloak, it was possible to see that I was accessing facebook.com as well as my bank’s website, though those websites did use encryption so I couldn’t see anything other than the URLs. When I disabled the option to securely send emails, it was even possible to see the text of messages I’d typed. After cloaking, everything I did showed up as a jumble of nonsense characters, as the Cloak VPN encrypted everything.

In a real world scenario, Cloak would effectively hide your data from other network users in a coffee shop, hotel, or any other location with no- or low-security WiFi set up. Even if you think you’re protected, be sure to check out all the sites you visit regularly; many of them use secure logon pages (you’ll notice the URL starts with https://), but then they revert back to unencrypted HTTP to deliver your content, so people could still see what you’re shopping for, reading, etc.

The Mobile Experience

Due to the nature of iOS itself, the Cloak app doesn’t really control the show; it acts as a front for your account, and contains a link that lets you install a VPN Configuration Profile, which is basically a bundle of settings that configure your iDevice to connect to the Cloak VPN. The install process is a snap—a couple screen switches from the Cloak app to a website that downloads the Config Profile, then a couple quick taps in Settings to install the VPN and you’re done. The only real configuration options available are whether Cloak activates On Demand (whenever you or an app attempt a network connection), or whether you manually enable the VPN from Settings. When you’re cloaked, the app shows that you’re “Securely Cloaked,” and a VPN logo is displayed next to the WiFi logo in your iDevice’s title bar.

The Desktop Experience

On the desktop, Cloak offers more options, though it stays true to the company’s goal of easy-to-use software. You just need to do a quick download from Cloak’s website, then the app does all the rest, including securing your connection automatically when you’re on an untrusted network. A small Cloak icon appears in your Mac’s menu bar, where it indicates your cloaking status via color changes and gives you access to Preferences. Cloak is a headless app (meaning it doesn’t appear in the Dock), so the menu bar is your only point of interaction.

For the more adventurous or technically savvy, Cloak offers some great advanced features, as well. You can toggle whether the app trusts (i.e. doesn’t secure) wired connections or password-protected WiFi networks, and also build a list of trusted networks such as your home or office so you don’t have to wait for Cloak to establish a connection before browsing. Disabling the trust of password-protected networks is a good idea, as WEP-secured networks still count as password-protected, but aren’t really secure. There is an option to you use Location Services to optimize your connection to the closest Cloak VPN server, as well as the ability to utilize a Cloak HTTP proxy server to speed up browsing.

One of Cloak’s coolest features on OS X is OverCloak, which blocks all outgoing connections on untrusted networks until you’re securely cloaked. You get a friendly pop up warning via the Notification Center that you can’t connect to anything until your Cloak is safely in place, and a handy Safari warning reinforces this. OverCloak is not only a great feature, but it’s also a fantastic example of great user interface design—rather than scratch your head at your inability to check Facebook, Cloak gives you a friendly, well-explained reason why your webpage isn’t loading right away.

If yo find yourself on the go using unsecured WiFi networks, Cloak provides a great way to shield your data from prying eyes, whether you hit a coffee shop a few times a month or spend a majority of your time on the go. The Mini plan is great for casual browsing, while the Pro plan mets the needs of more demanding business users. The Cloak team has done an extraordinary job building software that achieves not only security, but also simplicity; the time, effort, and headache of setting up your own VPN make it impractical for almost everybody. Cloak’s solution is simple enough for anybody to use, yet provides you with an extra layer of security when using public or untrusted WiFi networks.

You can sign up for a free 30-day trial of Cloak at their website; thereafter, monthly plans are either $2, $8, or $15 a month, depending on how much data you need. If network security or general technical geekery is your thing, be sure to check out the company’s support page, especially the “For Savvy VPN Users” and “Technology Deep Dive” sections (TLS, OpenVPN, and netstat, oh my!).

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