When comparing Cloak vs Bartender, the Slant community recommends Bartender for most people. In the question“What are the best power user tools for macOS?” Bartender is ranked 13th while Cloak is ranked 27th.
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Pros
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 Cleans up the menubar so it's less cluttered
Pro Great customisation options for the menu bar
Pro Lean and efficient
Does what it is supposed to do efficiently.
Cons
Con Hasn't published server/data center locations
Con OSX & iOS Only, without even manual configuration instructions for Linux/Windows
Con Expensive
$15 for download or $7.50 for upgrade if you have Bartender 1.