On the road to Windows 10: Rollout plans and rumors

Windows 10 will roll out in three distinct phases, but there are still many unanswered questions about timing. Here’s what to watch for as July 29 draws near

On the road to Windows 10: Rollout plans and rumors
Credit: Pixabay

We all know Windows 10 will start rolling out on July 29, but where will it roll? And how fast? It turns out we have very few details. So for those of you who support users who may be upgrading themselves to Windows 10 -- it's time for a little caution.

Consider the numbers: There are roughly 1.6 billion Windows machines worldwide; 850 million of those check into the Windows Update mechanism every month. An unknown number of Win7/Win8 users -- let's guess 500 million -- aren't under a volume license, and thus qualify for a free upgrade. There are 5 million registered Windows Insiders, although it isn't clear how many have actually installed the Windows 10 Technical Preview, much less kept it updated. And we have an unknown number of Win7 SP1 and Win 8.1 Update users who have signed on for the upgrade, thanks to Microsoft's advertising in the system tray and the GWX program.

That's one humongous bunch of custom installations. They won't all get Windows 10 at the same time.

In Satya Nadella's Earnings Conference Call on July 21 -- the latest information I can find -- Nadella said this about the Windows 10 rollout:

There are three distinct phases. The first phase is what I'll describe as the upgrade phase, that's what starts in a week's time.  And that is more retail execution and upgrades.  Then come the fall you will see the devices from all the OEMs going into the holiday quarter.  And then the enterprise upgrades. In fact, we have a release of enterprise features which I mentioned in my script, which will ship in that timeframe and I expect piloting to start and deployments to start in the second half of the fiscal year.

Note that the second half of Microsoft's fiscal year starts on January 1, 2016. Clearly, Microsoft isn't pushing enterprises to upgrade anytime soon. Consumer cannon fodder goes first, of course.

Here's how I see the rollout going, in concrete terms.

First, Windows Insiders -- probably just those in the Fast ring -- will get the RTM version (yes, I know that isn't the official term) on July 29. I'd be willing to bet the RTM is just a relatively small update to build 10240. After all, Insiders have been receiving patches and fixes disguised as Security Updates almost daily for the past two weeks.

The RTM version will only be pushed as an in-place upgrade. I have no idea when the ISOs will arrive, but Microsoft insists that once you've upgraded you can run a Reset (Start > Settings > Update & Security > Recovery > Reset this PC) and get a clean install. Pirate ISOs will, of course, flood the pirate distribution channel.

Next, I'd be willing to bet that those Insiders in the Slow ring will get their updates.

At some point Microsoft needs to cast the net a little wider and allow upgrades to Win7 SP1 and Win 8.1 Update PCs. My guess (again, it's only a guess) is that Insiders will be allowed to perform those upgrades first, before unleashing the Pamplona ninja cats on the GWX crowd.

Once the wailing has died down and the telemetry comes through relatively bloodless, expect to see the upgrade roll out to those who have signed up through GWX. They'll probably be upgraded in batches. That's when we'll see if the real pioneers survive.

I doubt that Microsoft will release any upgrade numbers, but it'd sure be interesting to see how many people get upgraded by the time the GWX crowd goes through. 

Once the GWX group has been processed -- we're probably talking a month, or even two -- I expect Microsoft will redouble its efforts to push out advertisements to computers that didn't get ads in the first round. Those appear to include PCs with old hardware, possibly with programs that are known not to work on Windows 10.

Somewhere along the line, in the next few weeks to few months, every Win7 SP1 or Win8.1 Update computer that qualifies for the Current Branch for (forced) updates should be able to upgrade through Windows Update. Whether the owners will want to upgrade is a completely different story, but Microsoft's marketing machine is already churning.

Those on the Insider Fast and Slow rings will stay in their rings unless they opt out. I haven't seen any announcements about signing up for the Insider program if you aren't already in, although I expect they'll show up soon.

USB drives with Windows 10 are currently for sale on the usual software supply sites. A few pictures of the USBs have found their way onto the Internet, although none of them appear to be shipping through legitimate channels as yet. I've seen no mention of DVDs with the Windows 10 bits.

What about corporate users? I don't see any push at all to deploy Windows 10 in the enterprise for several months. Just for starters, none of the update support infrastructure is in place. At this point, the vaunted Windows Update for Business hasn't made an appearance outside of Microsoft, even though it was announced in May. Nobody seems to have any details on how it's going to work.

Windows Server Update Services (WSUS) has a few new checkboxes for Windows 10 (see Rod Trent's article in WindowsITPro), but there's been no hands-on experience with it. I'm particularly interested to see how WSUS/WUB interacts with the Defer Updates checkbox in Windows 10 Update's Advanced Settings box.

It may not even be possible to upgrade enterprise PCs until those pieces are in place.

But that's only part of the story.

The long-rumored Win10 Service Pack 1… ooops, I should say "Threshold 2"… should be out in October. It isn't clear why Microsoft will be holding on to updates in the interim, given the Windows-as-a-Service meme, but all signs point to significant improvements to Windows 10 in October. Perhaps we'll see a worthwhile OneDrive app, or Skype off the desktop, or a Universal Photos app that does something, or… well, you get the idea. The 'Softies are also on the hook for Enterprise Data Protection, which won't appear in August, and for the promised ability to side-load corporate apps from the Windows Store.

Who knows? We might even get an alpha of Windows Update for Business in October.

At this point, none of the admins I spoke to have a clue how to control Windows 10 updates using WSUS. There's supposed to be an ability to delay feature updates (and possibly security updates) for up to a few months, possibly longer, but it's MIA. The general concept, like Windows 8.1 Update 1, is that an admin can sit on updates until the next Service Pac… uh, bunch of updates appears, at which point security patches get cut off. Again, lots of hands being waved, but no actual products.

One more rumor pointing to October… widespread leaks (and no actual facts) point to a much-improved Surface Pro 4 landing in October. Perhaps the new snap-on slate awaits Threshold 2?

Time will tell.

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