When comparing Cloak vs Divvy, the Slant community recommends Divvy for most people. In the question“What are the best power user tools for macOS?” Divvy is ranked 17th while Cloak is ranked 27th. The most important reason people chose Divvy is:
Although it's not in the same level as something like bug.n, Divvy does support the use of keyboard shortcuts to move windows about. You can even create custom shortcuts.
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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 Has keyboard shortcuts
Although it's not in the same level as something like bug.n, Divvy does support the use of keyboard shortcuts to move windows about. You can even create custom shortcuts.
Pro Requires virtually no configuration & is very easy to use
Divvy uses a drop and drag style UI that's simple to use and doesn't require any setup or configuration to get started.
Pro Reasonably configurable
You can change the grid dimensions and a very other visual settings to suit your needs.
Pro Super-fast access by defining your own hot key (mine Win+S)
Cons
Con Hasn't published server/data center locations
Con OSX & iOS Only, without even manual configuration instructions for Linux/Windows
Con Quite inconvenient to assign windows
You always have to use the mouse instead of having proper keyboard shortcuts.
Con No longer updated
While this may work for current machines, the last beta version (to be found on the site) is from January 2016.
Developer's twitter account has stopped being active as well, on November '16.
Con Windows 10 buggy
Not all keyboard shortcuts work. Support is non existent.
Con Installer requires admin rights, installs itself to AppData of the used account
Something to consider if would be used in a restricted environment.
Con Not free
Costs $14.