There's been a lot of discussion around who will be eligible to take advantage of the Windows 10 free upgrade plan when Microsoft's new OS releases later this summer. If you're already unfamiliar with what I'm talking about, take some time to read our coverage on Microsoft's announced Windows 10 upgrade plan in, Windows 10 Free for a Year for Windows 7, Windows 8.x, and Windows Phone 8.1 Upgrades. I won't go into that here, but instead have cobbled together some notes from a recent discussion with Microsoft that should prove interesting to some, but valuable to most.
Keep in mind that this is the "unofficial" plan right now, and things most certainly could change before the final release. However, this is the framework that Microsoft is currently working from, so no matter what it will eventually look like, it will resemble it in at least some small part.
So, the "unofficial" plan at this point is to offer the upgrade to any Pro or Core machines that connect to Windows Update. This, right here, confirms that the Windows 10 upgrade will deliver through Windows Update to Windows 7 and Windows 8 PCs.
Enterprise computers, though, will not be upgradeable through Windows Update. And this makes perfect of sense, considering most organizations require control over updates and upgrades. Instead of pushing the upgrade from Windows Update, Enterprise SKU computers can be upgraded using normal methods such MDT, Configuration Manager, task sequences, standalone media, or other customer deployment processes.
Software Assurance is where things get a bit sticky. Enterprise customers can upgrade Windows 7 and Windows 8 computers "for free" if still covered under SA. This means companies need to ensure that licensing hasn't expired by the time Windows 10 releases. For example, say SA expires on May 1st and Windows 10 hits general availability on July 1st. In this case, Windows 10 Enterprise will not be a free upgrade.
Bottom line: take the effort now to ensure your SA contract is current or will be current when Windows 10 releases. Most are saying Windows 10 will officially release at the "end of summer," meaning sometime in September. But, Microsoft is intending to start releasing new Builds quicker, and if things go well, GA could happen a lot sooner.
Of course, there is a real life hack here if the SA contract did expire and you wanted to upgrade anyway – just downgrade the machine to Pro, connect to Windows Update and let the upgrade commence.
There are those companies that allow employees to get updates from Windows Update, but may still want to keep Windows 10 from performing the upgrade. Microsoft is looking into ways of providing blocking mechanisms (probably a registry value) so even those utilizing Windows Update for security patches in businesses can still control Windows 10 upgrades.