When comparing Spectacle vs Cloak, 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 Spectacle is ranked 35th. 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 Free and open source
Spectacle is licensed under MIT with source code available on GitHub.
Pro Simple hotkeys
Spectacle offers easy-to-remember preset hotkeys.
Pro Mouseless
All windows in Spectacle can be controlled with keyboard shortcuts, so no mouse is needed. This makes for a fast way to control windows.
Pro Great UX
Spectacle is easy to use and configure. It's plug and play.
Pro Low footprint
Spectacle only uses up 18-19 MB of RAM, which means there is not much overhead by using this app.
Pro Multi-monitor support
Pro 7+ years of use
Using it for 7 years
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.
Cons
Con Not maintained
The software is free, but no longer seems to be maintained.
Con Impossible to add new functions
While keyboard shortcuts can be changed for the available actions, there is no way to add custom actions which in turn limits the functionality of the app.
Con Limited window sizing capabilities
You can use 1/2 of the screen vertically and horizontally (divide into 4 parts). You can also use the screen in thirds too, but only the left and right third: you can't use the 1/3 in the center. There is no way to do a more granular distribution.
Con Breaks on macOS High Sierra / Chrome or Firefox
Doesn't support side by side windows.
Con Doesn't work with any Adobe products
There are some apps like Adobe Reader that do not work with Spectacle. Basically, any app with a heavily customized UI that breaks OS X accessibility will not work correctly under Spectacle.