Easy to setup, easy to "set and forget". But, that's only when the Cloak servers are responding and running as normal. I have found that often (10% of the time approx) when trying to use wifi the Cloak servers are not responsive/down and that leaves you in the exactly the situation you don't want to be in... either using iOS and OSX on unsecured connections or not using them online at all. Pretty poor outcome for something that you actually pay for.
I travel a lot, US and EU, and use airline club, airport and hotel connections - all of which make me nervous, especially because I check my IRAs 2-3 times a day. Cloak is the third VPN I've tried - I don't remember the names of others because I quickly abandoned them when I found them kludgy and hard to set up. Cloak is SO easy, and shows up as a simple iOS setting choice. I see no speed impact, although I suspect there may be one, and so when I'm connecting to a slow service, I may use it only when transmitting or receiving sensitive data. Like seatbelts and life jackets, the easier they are to use, the more likely they are to be used. Cloak is easy.
The only VPN service that offers: - auto-connect on untrusted networks - kill-switch on untrusted networks This way I never forget to enable VPN on unknown wifi's and when I'm at home or work the VPN is not enabled so I have full speed.