I've been struggling with getting my Windows Server 2025 systems to properly install updates through WSUS. Here's what's happening: we have WSUS set to automatically download and install updates for our test servers every Wednesday at 5 PM via a Group Policy. When the time comes, the cumulative update installs without issue, marking a 'pending restart' status. However, other updates like the Windows MSRT and Visual C++ updates just sit there with an 'Install' status and never actually get installed. What's more, the servers don't reboot even though they're supposed to at 5 PM to complete the updates. As it stands, I have to manually RDP into each server to install these remaining updates one by one, followed by a manual restart to finish everything off. Has anyone else run into this, or know why the other updates won't install alongside the cumulative update? I get the trend but haven't found a solid fix yet.
4 Answers
I've seen similar issues with older versions of Windows Server too. In my case, I bypassed WSUS for timing by using Task Scheduler and the PSWindowsUpdate module to control when updates happen and force reboots. Setting tasks to download updates and rebooting without relying solely on WSUS brought more reliability to the process.
Just a heads up, make sure PSWindowsUpdate works well, as it sometimes requires additional setup on newer systems.
It sounds like a tricky situation! Have you thought about running some local tasks to mimic your manual installation process? Using PowerShell scripts or even Task Scheduler could automate it a bit more. Since the usual update queue isn't working as it should, taking control of the process might help.
For reboot management, I’d recommend checking for event 1076 in the logs to see if a reboot was initiated but not completed. If those events are missing, your servers might not be trying to reboot at all. It could be useful to tweak some timeout settings in the registry to help with shutdown and reboot processes, provided you dig into what's holding things up.
It might help to check if this behavior occurs on a fresh Server 2025 instance that doesn’t have your usual GPOs applied. WSUS is mainly for delivering the updates and doesn’t manage the installation process itself. On my end, I have a few Server 2025 VMs using WSUS with no issues, so it might be specific to your configuration.
That's a great idea! I’ll look into using Task Scheduler for this.