Best Practices for Managing Windows Server Updates in a Production Environment

Windows Server General
#1

Hi everyone,

I’m looking for advice on the best practices for managing Windows Server updates in a production environment. I currently oversee several Windows Server instances, including both on-premises and cloud-based deployments, and I want to ensure updates are applied efficiently while minimizing downtime and avoiding potential issues.

Here are a few specific concerns I have:

  1. Scheduling Updates: What’s the best approach for scheduling updates? Do you follow a specific patching cycle (e.g., monthly, quarterly), and how do you minimize disruption during updates?
  2. Testing Before Deployment: How do you test updates before rolling them out to production? Do you use a dedicated staging environment, and if so, what’s your process for verifying that updates won’t break critical applications?
  3. Automating the Process: What tools or scripts do you use to automate Windows Server updates? I’ve looked into WSUS and SCCM, but I’d love to hear what works best for you in different scenarios.
  4. Rollback Strategy: In case an update causes unexpected issues, what rollback strategies do you have in place? Are there specific best practices for ensuring a quick recovery if an update goes wrong?
  5. Handling Feature vs. Security Updates: Do you treat security updates differently from feature updates? If so, how do you prioritize which updates to install immediately and which ones can wait?

I’d appreciate any insights, recommendations, or resources that have worked well for you. Looking forward to hearing about your experiences!

I have also checked this: https://community.serveracademy.com/t/question-about-using-server-manager-in-an-azure-environment/golang

Thanks in advance for your help and support.

#2

Hi @romied

Let me answer your questions here, but you can also check some answers in a post here:
Need Help with Server Maintenance Best Practices

These two links can provide answers to your questions or a different point of view.
Windows Patch Management: Best Practices For 2024

Prepare a servicing strategy for Windows client updates

Scheduling Updates: With your servicing tool and usually after 2am local time. Maintenance typically can be from 2 to 5 am. Patching is done monthly and critical first, the the rest in a separate update session.
Testing Before Deployment: Test in a group of clients/servers that are non-critical and redundant.
Automating the Process: Usually your servicing tool might be able to automate.
Rollback Strategy: For a “quick” recovery, maybe reverting a snapshot or from backup.
Handling Feature vs. Security Updates: these do have a difference. Critical and security and then the rest of the updates.

-Ricardo