Being a heavy Windows and (old Android... all my devices run 4.4) Android user and having just transition to Samsung Galaxy S5 Android 6.0.1 I've got to say there is only ONE company that, PARADOXICALLY, gets how to treat consumers with a LIGHT hand and it's Apple and Apple's current approach to iOS is also illustrative as to why Cortana failed!
Before you write me off as an iPhone ****** follow my train of thought. I must confess I am at risk of becoming a fan of the iPhone because of Microsoft's and Google's approaches with Windows and Android, respectively
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Microsoft and Google are now all about click-bait advertising and click-bait notifications in their OS or apps AND YOU CAN'T DO ANYTHING ABOUT IT. The only solution is to not use the software at all and that's not a viable option. Their hand in 2018 is VERY HEAVY.
It's becoming increasingly difficult to customize Microsoft's and Google's software software while Apple has gone 180 degrees in the other direction.
I recently set up a 16 GB iPhone 6 for my partner and was shocked by how little bloatware and click-bait there was on iOS to begin with. The little click-bait that there was could be turned OFF COMPLETELY with a simple setting. And, you could REMOVE (i.e. truly delete, not just disable) all but SEVEN apps.
Yes, you read that right. Only SEVEN apps were left on the ENTIRE device (Phone, Message, Safari, Wallet, Settings, and two others (Photos and Camera?)). All of the other apps actually were DELETED.
iOS will now even apparently off-load rarely used apps to the cloud if your iPhone is running out of space and download them on an as-need basis.
Try that with a non-rooted Android phone and that would NEVER be possible. You'd be left with a gaggle of Google apps. If it weren't for the fact that I WANT the Samsung hardware I would've gotten myself an iPhone 6 (at nearly double the price of a used Galaxy S5). Now that I've seen how horrible modern Android is (v. 6... imagine 7 is even worse) Android has become compared to 4.4 I really appreciate what Apple is doing with iOS.
Google has the advantage of being an "incumbent" and is in control of Android so they get to pull their heavy handed click-bait news and omni-present search in "stock" Android. They can get away with it because consumers don't have much of a choice.
On Windows I use the Windows key to search my computer for apps and documents ONLY--I DO NOT WANT TO SEARCH THE WEB, EVER FROM WINDOWS KEY. That's why I have a browser with a search bar.
The only way to avoid web searches was to completely avoid Cortana and not do certain things which is what I used to do. And, now that I've succeeded at hiding Cortana from Windows 10 by executing all sorts of regedit kung fu I am a MUCH happier Windows 10 user.
To a substantial extent that's why Cortana never took off. She was FORCED on you in Windows if you wanted even some fairly basic functionality. This left a lot of people soured on her. She also isn't exactly easy to use on a desktop and she had hardly any presence on mobile where devices have good microphone--a prerequisite for using a VOICE activated assistant.
Cortana's failure is emblematic of Microsoft's inability to get consumers. And, Apple's latest iOS is emblematic of what Apple is doing right in the face of Google's and Microsoft's increasingly heavy hands.
Samsung Android 6 is so full of UNREMOVABLE bloatware--including Google's--it's frustrating. Even stock Google is full of an extremely heavy hand. If you want, for example, to use the "stock" Android launcher Google Now Launcher you are FORCED to accept click-bait news and you cannot ever remove the Google search widget. The basics of the Google Now Launcher I find the best (icons, animations, light-weight, even the feed cards), but, I like my home clean to be simple and clean and the Google search bar is anything but simple and clean and the click-bait news is ALWAYS present in the feed and CANNOT be turned off (c'mon Google, learn from Apple).
Anyway, long story short, Cortana is dead because Microsoft abandoned mobile and because Microsoft doesn't understand that desktop users used to freedom are not inclined to accept heavy hands. (we'll see if Windows 10 S fails as miserably as everyone seems to expect it to).