When comparing Cloak vs Notational Velocity, the Slant community recommends Notational Velocity for most people. In the question“What are the best power user tools for macOS?” Notational Velocity is ranked 16th while Cloak is ranked 29th.
Ranked in these QuestionsQuestion Ranking
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.
Pro Syncs with SimpleNotes or Dropbox
Pro Simple and minimalistic
The interface is clean and unobtrusive.
Con Hasn't published server/data center locations
Con OSX & iOS Only, without even manual configuration instructions for Linux/Windows
Con Feels a bit outdated
The last release was from 2011. Although due to its brilliant simplicity in doing what it's designed for, some might think there hasn't been any need for an update, as long as it still works with the newer OSs.