When comparing Cloak vs ShiftIt, 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 ShiftIt is ranked 46th. 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 Easy to configure
ShiftIt is configured through a simple UI where you simply press the hotkeys you wish to map to a certain action.
Pro Free
Pro Intuitive
ShiftIt is very straight-forward to use for most frequent usages.
Pro Open source
Pro Configuration can be committed to your personal dotfiles repository
Configuration winds up living in .hammerspoon/init.lua and .hammerspoon/Spoons/ShiftIt.lua. Very easy to track configuration changes.
Cons
Con Hasn't published server/data center locations
Con OSX & iOS Only, without even manual configuration instructions for Linux/Windows
Con A little slow
Similar to Spectacle, but it has a few more features, such as being able to pick the size adjustment increments. Spectacle was a little faster, though. Repeated size changes or moves in succession can cause it to wait for it to complete.
Con Imprecise when readjusting sizes
Con Doesn't support moving windows between workspaces
There's no way to move a window to a different workspace with hotkeys in ShiftIt.