Why isn't Microsoft pushing Windows 10 Mobile harder to WP8.1 users now?

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Back in March this year, Microsoft released the official Windows 10 Mobile upgrade to all eligible devices - so that's a whole load of Snapdragon 2xx, 4xx and 8xx-based smartphones* all right up to date with the latest and greatest OS, and all now on the Anniversary Update, right? Actually no, the vast majority of Windows Phone 8.1 users, many with fully W10M compatible phones, are still on 8.1 because Microsoft hasn't told them about the upgrade.

* the list, famously, didn't include the Snapdragon S4 generation (Lumia 920, 1020 etc.), but we've covered that old chestnut before, so let's not get bogged down here!

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As I said at the time:

Good to see this making it's way out into the real world of every day users and not just Insiders anyway. Though it'll take some email marketing for the former to know about installing the Upgrade Advisor, so that'll take a few days....

Eventually this update, once Microsoft is happy with how it's going (i.e. monitoring problems, etc.), will be provisioned and pushed without the need for the Upgrade Advisor installation and acceptance.

The sequence here is surprisingly sensible. The nightmare scenario was Windows 10 Mobile being made available to 50 million people at once and the various support mechanisms deluged in mass complaints - the opt-in system via Upgrade Advisor will both keep the less keen away for a bit and will drastically limit upgrader numbers for this first phase.

Very sensible analysis from yours truly at the time, I'm sure you will agree. Except that 'a few days', 'eventually' and 'for a bit' have all morphed into 'not yet, six months later'!

Now, there are some mitigating factors from Microsoft's end. I'm sure they've been monitoring feedback from non-Insider user progress after the big Windows Phone 8.1-to-W10M upgrade - and I'm presuming that they were concerned enough about the changes the user sees and/or performance issues that they've been holding off emailing the wider Windows Phone 8.1 user base and, you know, actually telling them that there's this big upgrade and providing a link to the Upgrade Advisor utility.

Which is fair enough on balance - anyone reading AAWP regularly will know of all the instabilities and issues which still exist in Windows 10 Mobile, even after the Anniversary Update. Even today, in October 2016, is it really a good idea to encourage Mr or Mrs Average to 'upgrade' what is presumably a stable and familiar friend of a phone and interface to an experience which is undeniably more future proof but which is also demonstrably slower and buggier? Probably not, which is exactly why Microsoft hasn't done a series of mass emailings.

By the way, in case you're wondering why Microsoft went with the whole Upgrade Advisor thing and simply didn't make Windows 10 Mobile available as an over-the-air system update to all eligible handsets, the answer is mainly down to space on user handsets. As AAWP readers and geeks we're used to keeping plenty of free space on our internal storage, in order to keep the smartphone running sweetly and to be ready for OS updates. Average users don't think that way - just check on some of your family and friends' phones - the chances are that they're full to the brim, with little space left. To upgrade in-place to W10M needs at least 3GB free, and preferably a lot more, which is why a triaging utility like Upgrade Advisor is needed - to walk general users through the space check and to help them backup and archive stuff as necessary.

Will there ever be a time to start pushing Windows 10 Mobile harder then? Maybe a push to all registered Lumia 930 or 830 owners? That sort of thing, and then see how it goes? Normally I'd have said 'No, leave users be on Windows Phone 8.1 unless they come looking for the update'. However, there's now the Skype factor to consider. 

Since March we've had Microsoft announce its plans transitioning Skype to a whole new architecture, followed only yesterday by news that the old Skype 8.1 client isn't even in the Store anymore, so any 8.1 users needing to rebuild their phones (even via Windows Device Recovery Tool) won't get Skype back. And even if they did, the Skype client for WP8.1 is going to stop working in a few months anyway - official support has already stopped.

At which point I'd argue that the demise of a fairly high profile component of Windows Phone 8.1 is probably important enough to at least communicate something to existing users. Now, I do realise that:

  • 8.1 users aren't that big a part of Microsoft's ecosystem anymore
  • not every 8.1 user was an active user of Skype too

But - equally - abandoning several tens of millions of users and saying 'Sorry, but you can't do that anymore' isn't going to play well in terms of PR, when the time comes to pull the plug on the old Skype sub-system.

Lumia 930

What should Microsoft do? At the very least, I think the time has come for an email to go out to registered Windows Phone users, certainly those registering W10M-eligible devices between 2013 and 2015. Something along the lines of:

"Dear valued Microsoft customer and Skype user,

In order to improve our Skype service going forwards we're changing to a new way of doing things and unfortunately the old Windows Phone 8.1 Skype client has had to be withdrawn. In order to keep yourself connected to friends and family going forwards you'll need our new Skype 'universal' client, which runs on Windows 10.

We're pretty sure you'll have heard of 'Windows 10' and may even now be using it on your desktop or laptop - well, there's a version of Windows 10 Anniversary Update for your phone and it will not only give you full Skype functions back but also upgrade many of your applications and improve the general interface. 

Make sure your phone is fully charged and that you won't need it for a couple of hours, then run our Upgrade Advisor utility from the link below. This will do some checks and lead you through into upgrading your phone from Windows Phone 8.1 to Windows 10 Mobile. It'll take a while but it's worth waiting for and all your stuff should stay intact, don't worry."

It's entirely possible that many people with eligible phones will miss the email, and many more will decide that they don't need to do anything about it because they 'don't really use Skype anyway', but at least the effort will have been made and Microsoft will have communicated with the (realistically) millions of Skype users on 8.1, offering a way forward. [So if anyone complains, "Read our previous email" applies, etc.]

(Of course, there should probably be another email, this time sent to all registered users with non-W10M-eligible phones, pointing out that Skype will stop working soon and that there's nothing anyone can do about it, but that'll be a much harder one to phrase tactfully, so I'm not even going to attempt that!)

Comments welcome on my strong suggestion to Microsoft and to my suggested timescale - do it this month.

(Hat tip to MSPU, which asked this very question of its readers last week - consider the feature above my answer!)