When comparing Cloak vs TotalTerminal, the Slant community recommends TotalTerminal for most people. In the question“What are the best power user tools for macOS?” TotalTerminal is ranked 20th while Cloak is ranked 27th. The most important reason people chose TotalTerminal is:
TotalTerminal is a plugin for Terminal.app. It provides persistent Visor Window which slides down when you press a hot-key.
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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 Allows quick access to the terminal system-wide
TotalTerminal is a plugin for Terminal.app. It provides persistent Visor Window which slides down when you press a hot-key.
Pro Quake style window show/hide
You maybe know or don't know Quake from Id Software. But this game had the best idea to hide/show a terminal window. Simply using full width but 26 rows. On show the widow slid down from top of screen. On hide it mode up to top edge of the screen until it disappeared. 2nd next best was the semi translucent background. You could still see through the terminal window while it was shown.
The same style is now available in TotalTerminal and iTerm2 (OSX Terminal replacement - no Terminal plugin).
Cons
Con Hasn't published server/data center locations
Con OSX & iOS Only, without even manual configuration instructions for Linux/Windows
Con No longer under active development
Con Doesn't work on El Capitan with SIP on
Apple introduced a new security feature in OSX El Capitan, called System Integrity Protection, that, among other things, does not allow augmenting Terminal. While it's possible to turn SIP off (instructions on how to turn off SIP and get TotalTerminal working on El Capitan can be found here) it is not recommended.