When comparing Roll your own VPN vs Cloak, the Slant community recommends Cloak for most people. In the question“What is the best VPN provider? ” Cloak is ranked 25th while Roll your own VPN is ranked 75th. The most important reason people chose Cloak is:
SSL pinning protects against some forms of man-in-the-middle attacks that even SSL encrypted traffic is vulnerable to. Not long ago, iOS did not allow for pinning but that may have changed more recently.
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Pros
Pro Single IP
Quite often with VPN services you get a shared IP, here you get one all to yourself. This means you are far less likely to be blocked.
Pro Cheap
Depending on your use case, a cheap unmetered VPS can cost very little.
Pro You control everything
"Is there logging?" "Do I get my own IP?" So many questions, easily answered by running your own service!
Pro Does SSL Pinning on OS X
SSL pinning protects against some forms of man-in-the-middle attacks that even SSL encrypted traffic is vulnerable to. Not long ago, iOS did not allow for pinning but that may have changed more recently.
Pro Responsive developer
The developer of Cloak is extremely responsive to feedback and quick to answer questions or support requests.
Pro Senses Trusted WiFi networks
Cloak can be set to not use the VPN on whitelisted WiFI SSIDs (like home/work).
Pro Unlimited devices (as long as they're OSX/iOS)
Unlimited devices and data per account, so you can connect up the whole family or office on one account if you so choose.
Cons
Con One location only
Unless you set up multiple boxes, you have to think about where you are getting your server. The advantage of many VPN services is that you can pick your location to get around geo-blocks.
Con Tougher to set up
OpenVPN in particular is not exactly trivial to set up.