When comparing Cloak vs Karabiner, the Slant community recommends Cloak for most people. In the question“What are the best power user tools for macOS?” Cloak is ranked 27th while Karabiner is ranked 29th. 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 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 Low-level key bindings/mappings
For example: Fn+C now calls up contextual menus for me with:
<!-- Fn + C = same as right-click mouse -->
<item>
<name>kybd control click</name>
<identifier>private.keybd_to_control_click</identifier>
<autogen>
__KeyToKey__
KeyCode::C, ModifierFlag::FN,
KeyCode::VK_MOUSEKEY_BUTTON_RIGHT
</autogen>
</item>
Pro Make FN key into a new modifier key for custom shortcuts across apps
Cons
Con Hasn't published server/data center locations
Con OSX & iOS Only, without even manual configuration instructions for Linux/Windows
Con Difficult to configure custom actions
Configuring custom actions requires editing an XML file with very strange syntax, for which it's difficult to find good documentation.