When comparing Cortana vs Enso Portable, the Slant community recommends Enso Portable for most people. In the question“What are the best power user tools for Windows?” Enso Portable is ranked 50th while Cortana is ranked 74th. The most important reason people chose Enso Portable is:
GChristensen recently upgraded Enso to Python 3.7, a great improvement over the original v2.5. You can write custom Enso commands in Python through its new web interface (or your favorite editor once you know where to put the files.) There's even an install command to pip install any Python package you need from PyPI. The sky's the limit.
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Pros
Pro Can recognize music
You can ask Cortana what music is playing and she will attempt to identify it.
Pro Will let you know when artists you're interested in play in your area
Cortana monitors your Bing search history, social network actions, music played, etc to find out what are your favorite artists and will let you know if they plan to play in your area.
Pro Extensible in Python
GChristensen recently upgraded Enso to Python 3.7, a great improvement over the original v2.5. You can write custom Enso commands in Python through its new web interface (or your favorite editor once you know where to put the files.) There's even an install command to pip install any Python package you need from PyPI. The sky's the limit.
Pro Optional quasimode
Letting go of CapsLock just feels faster than hitting enter (sometimes too fast: be sure to disable the reboot command before turning this on!) Even with quasimode enabled, you can make it modal for that command by tapping Alt.
Pro Easily teach the app to open specific apps and sites
There is a learning function to the app that allows the user to teach the app to open specific items by typing "learn as open" and then clicking on the item one wants it to learn to open.
Pro Can go to existing open windows
By using the "go" command users can switch to their already open windows making this a bit of a window navigator as well as a launcher.
Cons
Con Functionality is limited on non-Windows devices
While Cortana is available on Android and iOS, certain features on those operating systems are either limited or non-existant. For example, there's no hands-free voice activation on iOS, and on Android it's only available on the homescreen and nowhere else, etc.
Con Comes with a reboot command
And a shutdown command too. Installing these is optional, and I recommend that you don't, especially if you use the quasimode. Unless you like losing your work.
Con No message log
According to Raskin's philosophy which inspired Enso, a pop up "dialog" is a bad design. The OK button is a useless input that interrupts your flow. Enso's pop up messages, therefore, are transparent and quickly fade away on their own (like Android Toast messages). Unfortunately, this also means you can easily miss them if you're not paying attention. Raskin's solution was to keep a message log you can refer back to, but Humanized never got around to implementing that for Enso.
Con Usage tends to be slowed by the caps lock
Function of the app relies on the caps lock key being pressed to enter commands, which can slow some people down by having to hold that key down when they are typing commands.