Cloak vs Hammerspoon
When comparing Cloak vs Hammerspoon, 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 Hammerspoon is ranked 38th. 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 1512 issues are closed in the download page in GitHub
https://github.com/Hammerspoon/hammerspoon/issues
They do fix issues that come from the community.
Pro Deeply customizable
Hammerspoon's Lua scripting and broad API allows you to perform any action you can imagine on your mac. It hooks into many OS APIs directly and has some high-level APIs to manipulate things like Spotify or iTunes. See the full list here.
Pro Automate actions based on the operating system
Hammerspoon lets you hook into OS level events and trigger any action you can imagine. From setting up a simple keyboard shortcut to launching a complex workflow using multiple apps and scripts.
Cons
Con Hasn't published server/data center locations
Con OSX & iOS Only, without even manual configuration instructions for Linux/Windows
Con Has 324 issues on their download page in GitHub
https://github.com/Hammerspoon/hammerspoon/issues
I can not list all the issues.
Con Some knowledge of programming required
Hammerspoon is scripted in the Lua programming language, and some familiarity with programming in general will be needed to use it. Some plugins exist that can be used by adding some files to a specific folder, but this will not give the flexibility that is so key to Hammerspoon