According to Microsoft's Windows Update Twitter account, it has already initiated the training process for its machine learning engine that will determine when and how to push the Windows 10 May 2019 Update to systems that are running the Windows 10 April 2018 Update (or older).
Microsoft says that it is taking this step "to ensure we can continue to service these devices and provide the latest updates, security updates and improvements." Machines running the Windows 10 April 2018 will stop receiving security in mid-November, so this is just a preemptive move by Microsoft to ensure that its customers are running on the most up-to-date and secured versions of Windows 10 currently available.
📣 [Windows Release Health Update – New Message] We are beginning to train the machine learning based rollout process to update devices running the April 2018 Update, and earlier versions of Windows 10. Read more here: https://t.co/NHEQuEjsVX.— Windows Update (@WindowsUpdate) June 18, 2019
"For Windows 10 devices that are at, or within several months of reaching, end of service, Windows Update will automatically initiate a feature update," said Microsoft's John Cable last month. "Keeping those devices supported and receiving the monthly updates that are critical to device security and ecosystem health."
With the machine learning algorithms that Microsoft has in place, the software giant will only be pushing out the Windows 10 May 2019 Update to systems that will have the least amount of show-stopping incompatibilities. Microsoft was burned badly by the horribly botched release of the Windows 10 October 2018 Update and has made great strides to improve internal (and external) testing along with increasing overall reliability of its updates.