Why is my Windows Server 2016 taking so long to reboot after a recent update?

I've recently updated a couple of my VMs with the same update. One rebooted in about 5 seconds, while another took nearly 30 minutes but everything was still functioning during that time. It seems to vary between machines.

First off, make sure you have backups of your VMs before doing updates. It’s also helpful to check the startup logs for any processes that might be failing repeatedly, which could cause the delays.

It sounds like a common issue with Server 2016. I've experienced multiple updates that not only take a long time to apply but also can extend the reboot time significantly. You're definitely not alone in this.

If you're looking for options, upgrading to newer versions like 2019 or 2022 could help. Just make sure you have a rollback plan in case anything goes wrong during the upgrade. Most likely, you won't run into issues, but it’s always good to be prepared.

This slow reboot issue has happened to me a few times. Honestly, if it's a recurring problem, it might be worth considering an upgrade to Server 2019 or even 2022. Just remember that 2022 removes SMB 1.0 by default, so check if you need that for any older devices you have.