The Windows 10 upgrade process changed significantly in 2019. Previously, Windows 10 feature updates would be pushed via Windows Update to compatible systems shortly after release and official options to block these were limited to Pro and Enterprise editions of the operating system.
The release of Windows 10 May 2019 Update changes the process in several ways. Microsoft won't push feature updates to Windows 10 devices anymore automatically. The company will display notifications on compatible systems that inform the user or admin that a new feature update is available, but it won't be installed anymore automatically.
Administrators need to select the feature update explicitly so that it gets installed. The change goes hand in hand with a modification of the Windows Updates interface that separates regular updates and feature updates from one another.
Feature updates won't be enforced anymore going forward when they are released, and that is true for the two recent feature updates Windows 10 version 1803 and 1809 released prior to the May 2019 Update.
The change does not mark the end of enforced feature updates though. Microsoft will push feature updates to Windows 10 devices when the currently installed version of Windows is about to exit the support period.
Windows 10 version 1803, the April 2018 Update, will be the first version with enforced feature upgrades. Microsoft revealed that it will start to push updates to devices running the April 2018 Update in June 2019.
Windows 10 version 1803 reaches end of support in November 2019 for non-Enterprise customers. Enterprise support ends in November 2020 as Enterprise and Education editions get 30 months of support instead of the 18 months of support that Home editions get.
Starting this June, we will begin updating devices running the April 2018 Update, and earlier versions of Windows 10, to ensure we can continue to service these devices and provide the latest updates, security updates and improvements. We are starting this machine learning (ML)-based rollout process several months in advance of the end of service date to provide adequate time for a smooth update process.
Microsoft did not reveal the upgrade target version but it is likely that devices will get updated to the most recent version of Windows 10 which in this case is Windows 10 version 1903.
It is unclear if certain Windows settings will block the automatic update download and installation, or if the enforcement overrides all of them. For instance, will the update be downloaded if you set up all available network connections as metered?
Unsupported systems don't receive security updates or any other updates anymore; the lack of security updates leaves them open for potential exploits and attacks targeting these vulnerabilities.
For Windows 10 devices that are at, or within several months of reaching, end of service, Windows Update will automatically initiate a feature update; keeping those devices supported and receiving the monthly updates that are critical to device security and ecosystem health.
Some admins may argue that it should be their decision whether to upgrade or not; Microsoft believes that it is the company's responsibility to provide updates to systems that will run out of support or are not supported anymore.
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