How can I ensure all users in my org get notified about a pending feature update?

Hi Shane,

What your user described is actually expected behavior in many cases. With the newer Windows Update deadline policies, Windows is designed to handle most notifications automatically and may show only subtle restart indicators (such as the orange restart icon in the system tray) rather than persistent pop-up notifications. Microsoft specifically recommends relying on the built-in deadline experience and avoiding additional notification policies in most environments.

If you're already using a 2-day deadline and 1-day grace period, the update should eventually become mandatory and Windows will increase the visibility of restart prompts as the deadline approaches. However, there is no supported GPO that guarantees users will always see a toast notification regardless of notification settings, Focus Assist, user activity, or whether the notification was previously dismissed.

I would verify that you are using the modern "Specify deadline for automatic updates and restarts for feature updates" policy rather than older restart-notification policies, as Microsoft has shifted update compliance behavior toward deadline-based management.

If your goal is minimal user interaction, your current configuration is close to Microsoft's recommended approach. The most reliable indicator users will see is the pending restart status in Windows Update and the taskbar restart icon, while the deadline policy ensures the device will ultimately restart even if notifications are ignored.

Hope it's helpful to you! Please give it a vote if my answer clarifies your concern, thank you!

Harry.