Since there will be "no more versions of Windows" and "only updates to Windows 10", I'm curious how Microsoft will handle getting customers to "pay for Windows upgrades".

I assume either that assumption is false, and this is just another bait and switch from Microsoft, and they will make customers pay for "big updates" for Windows 10 in the future - or they will try to at least transition businesses to a subscription for Windows.

They're already seeding the idea that Windows 10 updates will not be free forever to unsuspecting tech writers by getting them to push headlines such as "Next Major Update Of Windows 10 Will Arrive In Month X, For Free"

First off, everyone already assumes that Windows 10 updates would be free, since Windows "updates" have always been free - so why even bother to put such a "useless" fact in a word-constraint headline? The only explanation is that they're trying to prepare the public for when Windows 10 updates will not be free, and make them think "Oh, so the version after that may not be free anymore?!" and set that expectation.

«Since there will be "no more versions of Windows" and "only updates to Windows 10", I'm curious how Microsoft will handle getting customers to "pay for Windows upgrades".»

Microsoft has stated pretty openly the obvious truth from OS surveys and telemetrics that statistically "no one" ever has paid for Windows upgrades. By far, statistically, consumers bought a PC and used whichever version of Windows came with that PC for the lifetime of that PC.

In Enterprise where the cost model already including support and servicing and Windows upgrades, there was plenty of feet dragging and Enterprises have statistically paid extra to not upgrade Windows and/or paid for upgrades that they've never installed.

Microsoft seems trying to "right size" the Windows pricing model by taking into account the reality that consumers were already expecting to pay for Windows only once in the lifetime of a device and that Enterprises "like" to pay more to not upgrade.

They do this with how the upgrades to Windows 10 worked in the first place:

Sell a license for Windows that is device specific.

When you buy a new/replacement device you 'need' to buy Windows over again. Upgrading that CPU/mobo? Time for a new copy of Windows too.

There will still be upgrades to Office, so they just need to tie that in. At some point your O365 subscription will include Windows updates, with newer Office programs refusing to install on "insecure unpatched versions", and that will be it.

Either you pay a yearly subscription for Windows Enterprise, or you get ads

Why not both? At least they're pushing them to the Pro version [1], as Microsoft seems to be trying to turn it into a more expensive "Home Premium", leaving professionals with only the most expensive Enterprise version as an option [2].

[1] http://www.infoworld.com/article/3101947/microsoft-windows/m...

[2] http://www.ghacks.net/2016/07/28/microsoft-removes-policies-...

They will eventually force you to a user based model.

now that apple dropped "OS X" and moved on to another naming scheme, MS is now free to follow suit.