In this age of Snowdens and NSA spying, you might be spending more time thinking about your privacy online. Unfortunately, public wifi—which many of us rely on every day—can be a huge opportunity for hackers and spies to grab your data and use it for nefarious purposes.

That’s where Cloak comes in. Cloak is a “VPN”—a “virtual private network”—that helps you keep your connection secure and hackers out.

Cloak is a VPN service that helps you secure your Internet connection.
Cloak is a VPN service that helps you secure your Internet connection.

Cloak starts at $1.99 per month—less than a cup of coffee at that café you loiter at. The base plan starts with 5 GB of bandwidth per month, and you probably won’t even come close to using it. VPNs have existed for ages, but at this price point subscribing is a no-brainer, especially when you factor in the beautiful and easy to use applications that Cloak has built. (The service is currently Mac and iOS-only.)

In this episode, my good friend Peter Upfold is my guest on the show. Peter introduced me to Cloak through a post on his blog, and I was excited to have him come share the service with the Wrapp Up audience.

Secure your Internet connection with Cloak – WU18 — Audio player


Secure your Internet connection with Cloak – WU18 — Transcription

Just a reminder, these transcriptions are prepared by I scan through them before publishing, but I don’t clean them up (too much). If things are hard to understand, listen to the show to see what we actually said!

Chris: Hello everybody, good morning, afternoon or evening, good morning, good morning, afternoon, evening etc. I am Chris Van Patten and after that long intro this is The Wrapp Up, which is a podcast about apps and web services and digital tools that help entrepreneurs and marketers and digital folks, developers, users everywhere.

This week we have a special guest, I’m super excited to welcome Peter Upfold, who is a long time friend and collaborator, a brilliant developer and system administrator and all sorts of things and he is based in the UK, welcome Peter.

Peter: It’s great to be here, thanks for inviting me.

Chris: We’ve known each other for a long time probably —

Peter: Probably too long.

Chris: Never too long, but it’s certainly been about ten years or very close to that. It’s funny how the time flies, but anyway, that aside, Peter has brought an app to share with us a web service and why don’t you tell us what that service is.

Peter: Sure, what I’m going to bring to the table today is the service called Cloak. Cloak is the VPN service so for those of you who don’t know what that is; basically the idea is you’re on a untrusted connected maybe, you go to accomplish something and you’re sharing the air with everybody else around you and you don’t really want people to be watching what you’re doing, maybe you’re logging into a site which doesn’t let you transmit your password securely and you don’t want everybody around you to get that password or just to have access to anything they shouldn’t.

The idea with a VPN is you connect securely to it, you send all your traffic to it and then it appears out on the Internet from that remote point, so everything on your network on the local network is completely encrypted and nobody can see into it.

Chris: That’s cool.

Peter: It’s a particularly — yeah, and it’s really nice though, it is Apple devices only so that they’re for a Mac client and they’ve got an IOS client as well so that there’s that so for some people it already isn’t interesting. It’s a really nice implementation I think.

You’ve got the iOS side now; with the iOS side there are limitations in what you can do with iOS in terms of what apps you’re allowed to do so it has to work with iOS with built-in VPN functionality so it uses the Cisco IP sect protocol which isn’t quite as good as it does, as the way it does it on the Mac but it’s very good.

You install the app, it will then extend you across to install a profile and then in the settings app on your iPad or iPhone or iPod Touch you will get the VPN setting will show up and you just flip that over to switch it on and from that moment on you get little VPN icon coming up in the status bar and all the traffic then is being secured. You can go to some around a person’s house, or you can get on in the coffee shop and you can work and you know that everything that you’re communicating is not visible to everybody on that local network. It goes securely across the Cloak and then appears out on the Internet from that point.

Chris: Excellent.

Peter: It’s nice that one.

Chris: When I think VPN or Internet security and all this kind of stuff it seems… Your first instinct might be to think about it as very technical and difficult to use and requiring coding and knowing about ports and protocols and all this stuff, but what I love about Cloak, as an outsider, is that they seem to be doing a lot of work toward making the process very easy and demystifying a lot of that and really making it beautiful which I think maybe is part of the reason why they only support Apple products at the moment.

Peter: Maybe, yes.

Chris: It seems like a very easy to use way to get this started. A little bit of a sidetrack, so the idea that VPN is that you’re passing your traffic through this saying to the VPN essentially, “Fetch me this website” and then it fetches it and then it comes to you in a sort of a very simplistic way.

In this age of Snowden and NSA and all this sort of stuff that’s been floating around, why should we trust Cloak or what makes using Cloak a better option than not?

Peter: This kind of story, very complicated, very quickly; at the moment; I don’t know how much to say given this is going out but there’s nothing that a casual user that doesn’t really understand technology is going to be able to do to protect yourself from the possibility of somebody with that level of resource from being able to see what you’re doing and I don’t think Cloak pretends to be designed to do that.

I’ve talked a little bit about the recent news stories about this in a blog and one of the things that attracted me to it originally is they actually wrote a blog post; this is before all this stuff happened, explaining exactly what, exactly how it worked but also what it could do and what it couldn’t do. They were really honest about this is the capabilities of this product and this is what we can’t do.

None of these VPN services are something that you should use if you’re trying to do something that’s, that you want to keep completely secret, but he odds aren’t about how, if you want to keep something completely secret it’s quite difficult to do anything electronic, ultimately.

The point I’m making I suppose is what I’d like to say, were really honest about that about this does this but it doesn’t do this, it doesn’t protect you from this; and I like that.

Chris: Yes, the transparency is really refreshing I would say in this sort of age of, you know we don’t really know how Facebook uses our data, we don’t really know how Twitter uses our data but they’re being very open and pro-active about saying that which I think is a good thing.

Just to briefly touch on the pricing, I’ll sort of just walk through their pricing chart here so it’s a $1.99 per month for 5 gigabytes of data; $7.99 a month for 25 gigabytes of data or unlimited at $14.99 per month, so really affordable.

I think my family has a cell phone plan that is limited to 6 gigabytes and we never even use it so I mean if you’re thinking oh, I probably use a lot, certainly for mobile you probably don’t use as much as you think and two bucks a month isn’t unreasonable at all.

Peter: Yes. There’s another real cool thing that I want to mention. I’ve talked a little bit about how the IOS product works it uses that built-in, you just go to the settings app and you just flip on the VPN. On the Mac they’ve got a dedicated app but presently you’ve got a lot more freedom on the Mac with the app to do what it wants.

It uses the open VPN protocol and the really cool thing about it is you can transfigure it to automatically switch on when it goes into a network it doesn’t know. You can teach it, these are my home networks, these are the networks that I trust and any time you connect to any other network it will actually shut off all of your outgoing connections, establish a secure connection to Cloak before then switching all the outgoing connections on again.

You can go somewhere and you know that nothing is leaking out between the time you connect to the potentially untrustworthy network and the time that Cloak is connected and securing your traffic and that’s a really cool feature, or particularly on the Mac side that makes it potentially useful for that scenario.
Chris: Very easy to save your gigabytes that way.

Peter: Yeah, and you don’t have to worry about when to switch it on and switch it off because it’s going to do that detection of oh, you’re on a trusted network or not and automatically manage that and it will come up with a little notification up in the top right saying, “I’m protecting you now” and then when it switches off you’ll know about that as well.

Chris: Excellent. The service is Cloak, you can find it at, it’s on Mac IOS, IOS6 or later and Mac 10.7 or later and there you have it. Thanks so much for coming on the show, Peter, and sharing Cloak with us.

Peter: It’s been great, thank you.

Chris: Where can people find you on the Internet?

Peter: You can find me at and I’m also on Twitter @PeterUpfold.

Chris: Excellent, we’ll put those links in the show notes as well as the link to Cloak. All right, thanks so much for joining us. This has been the Wrapp Up, we’ll talk to you next week.

Published by Chris Van Patten

I'm an entrepreneur and product lead, and owner of Tomodomo, through which I help companies build their digital publishing platform.

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