When you use public Wi-Fi, such as the service provided in a hotel or in a coffee shop, it is possible for someone else on the same network to use hacker tools to intercept data going to and from your computer, iPhone or iPad. This makes it possible for a bad guy to get your password as you are logging on to a site, or possibly even to read your confidential attorney-client communications. Is this actually happening to you? Unfortunately, there is no way to know, so all you can do is guard against it. A good solution is to use VPN — a virtual private network — to encrypt the communications from your device to some other location. For example, your law firm may have a way for you to create a VPN to your office, so even if you are on public Wi-Fi the traffic between you and your office is secure, and then you are essentially just as safe using the Internet as you would be in your office. But for this to work, your office must have VPN, and you need to remember to establish the VPN connection.
Cloak is a service that seeks to make it easy and automatic to use a VPN whenever you are using an untrusted public Wi-Fi network. Once you install the app on your iPhone or iPad, whenever you start using a Wi-Fi network, Cloak kicks in automatically and creates a VPN connection to encrypt all of your traffic. You can tell Cloak that a specific Wi-Fi network is trustworthy — such as the one at your home or at your office — and Cloak will remember not to turn on VPN at those locations. But as soon as you connect to Wi-Fi somewhere else, Cloak turns on the VPN to protect you again.
Cloak costs $2.99/month for only 5 GB of data or $9.99/month (or $99.99/year) for unlimited data. There is a free 30 trial if you want to see how the service works, and I've been trying it out for the last few weeks on my iPhone and iPad. (Cloak also works on a Mac, but I haven't tested that.) I'm really impressed with the service. It works behind the scenes so you don't have to worry about it, it doesn't slow down Internet traffic in any way that I could measure, and it provides protection.
When you first start the app, it will switch you over to a part of the Settings app that contains profiles, which is a part of Settings that you may never have used before. Simply click the install button to install the Cloak profile. You will need to enter your device password to confirm the installation.
Now, any time that you connect to a Wi-Fi network that you have not previously told Cloak that you trust, Cloak kicks in and establishes a VPN connection. You probably won't even notice that it happens because it happens quickly, invisibly and in the background. But if you pay attention to the top of your iPhone or iPad screen, you will notice the letters VPN in a box to tell you that you are using a secure VPN connection.
For example, I recently traveled to Orlando on business, and while waiting in the airport for my flight, I connected my iPad to the free public Wi-Fi. Without me doing a thing, Cloak realized that I had connected to an untrusted network and so Cloak established a VPN connection, as you can see from the VPN indication at the top left:
There is a Cloak app on the iPhone and iPad that you can launch to tell Cloak that you trust a network. When you change settings such as adding a new trusted network, Cloak walks you through a simple process to sync your settings so that the same settings are applied to all of your other devices. So if you are using your iPhone and tell your iPhone that you trust your home and your office networks, the next time that you sync settings on your iPad your iPad will also know to trust those networks.
When you use Cloak, you no longer need to worry about trusting everyone else who is on the same public network — which of course is usually impossible to do. Instead, you only need to trust the guys who run Cloak not to intercept your communications. Can you trust them? I'm reminded of a story I recently saw on PCMag.com about an Android app called Virus Shield that was the top paid app on the Google Play store for a while and promised to protect an Android phone against viruses for only $3.99, but it turns out that all the app did was display a fake checkmark, only pretending that it had done something to protect the device. You rarely see something like that on Apple's App Store, but it just goes to show you that you always need to be careful. So I asked the founder of Cloak, Dave Peck, to tell iPhone J.D. readers why we can trust his company. Here is his answer:
Q: Why should users trust your company?
A: That's always a good question to ask for any third-party VPN service. We've taken our best crack at this on our blog, here: Why Trust Matters When Choosing a VPN
Q: Couldn't one of your employees access my traffic since I am on your network?
A: Your traffic does flow through our network, so Peter, Nick, or I could indeed access it. (We're currently a three-person company based in Seattle, WA.) However, we have strict policies that fully enumerate the information we collect and what we do with it. You can find our policies here: https://www.getcloak.com/policies/
If you click on the links you get very complete answers on why Cloak is trustworthy. The company consists of three guys who used to work at Microsoft — you can see their pictures here — and the whole point of their company is to protect your communications. Obviously, it would destroy their business model if they broke this trust, and they have been doing this since 2012 and have received really good reviews over the years. After reading all of the policies and researching the company, I feel comfortable trusting Cloak to do what it promises to do and protect my privacy — and I certainly trust them much more than I trust all of the random people sitting in the Starbucks with me. Especially that one guy in the corner over there.
Cloak offers one more feature that I haven't found a need to try out, but it might be useful to some of you. When you use a VPN, it can appear to the outside world that you are accessing the Internet from another location. Your iPhone might be in Miami, but a secure tunnel carries your traffic to Seattle so a website might think you are in Seattle. Cloak includes a feature called Transporter that can let your iPhone or iPad appear to be in Australia, Canada, France, Germany, Japan, Netherlands, the United Kingdom or the United States. So if you want to stream video from the BBC that isn't available outside of the U.K., apparently you can make the BBC think that you are in the U.K. Again, not something that interests me, but it is there if it interests you.
I'm impressed enough with this service that when my free 30 day trial ends, I plan to sign up for the basic $2.99/month service to get a sense of whether I use more than 5 GB a month on public Wi-Fi networks. The company also sells through the iPhone app a one week unlimited pass for $3.99, which could be cheaper if the only time that you use public Wi-Fi is when you travel and you don't travel more than twice a month. Just don't forget to buy a pass before you start using the Wi-Fi at the airport, your hotel, etc.
Click here to get Cloak (free): 
