To upgrade, or not to upgrade. While that may not have been the question that Hamlet asked, it’s one you might be asking. You already made the mistake of asking Reddit, “should I do an in-place upgrade,” and, as expected, people had Big Opinions. A Windows Server Feature Update offers benefits, like performance and analytics. On the other hand, if you have problems, then your attempts can lead to business downtime and service disruption. Meanwhile, time rolls on toward the October 2025 end-of-service (EoS) for Windows Server 2016.
If you’re still trying to decide if or when to do a Feature Update, then these best practices for troubleshooting a Windows Server upgrade might help you.
What is an in-place Windows Server upgrade?
An in-place Windows server upgrade, also called a Feature Update, is when an organization updates an older operating system version to a new one without making changes to:
- Settings
- Server roles
- Data
By not requiring the IT department to reinstall Windows, the in-place upgrade reduces downtime and business disruption while improving security and system performance.
The process for an in-place Windows server upgrade is:
- Collecting diagnostic information for troubleshooting issues
- Backing up the server operating system applications, and virtual machines
- Performing the Feature Update using the Windows Server Setup
- Checking the in-place upgrade to see if it worked
Which version of Windows Server should I upgrade to?
Depending on your current operating system, you may have different supported paths:
- Windows Server 2012: Windows Server 2012 R2, Windows Server 2016
- Windows Server 2012 R2: Windows Server 2016, Windows Server 2019, Windows Server 2025
- Windows Server 2016: Windows Server 2019, Windows Server 2022, Windows Server 2025
- Windows Server 2019: Windows Server 2022, Windows Server 2025
- Windows Server 2022: Windows Server 2025
- Windows Server 2025: Windows Server 2025
Microsoft no longer supports Windows Server 2008 or Windows Server 2008 R2.
Reasons for Upgrading Windows Servers
Upgrading Windows Server provides many of the same benefits that updating other device operating systems (OS) provides.
1. Enhanced Security
As with any operating system, the Windows Server upgrades typically incorporate new security features. For example, Windows Server 2022 brought with it:
- Secured-core server: hardware, firmware, and driver capabilities to mitigate security risks during boot, at the firmware level, and from OS executing unverified code
- Secure connectivity: implementing HTTPS and TLS 1.3 by default, encryption across DNS and Server Message Block (SMB),
Meanwhile, Windows Server 2025 includes security upgrades for:
- Name and Sid lookup forwarding between machine accounts
- Confidential attributes
- Default machine account passwords
- LDAP encryption by default
2. Improved Performance
The OS updates improve performance by changing how processes work. For example, Windows Server 2022 improved performance with changes like:
- Encrypting SMB data before data placement
- Reducing Windows Container image sizes
- Improving both UDP and TCP networking performance
- Enhancing Hyper-V virtual switches with Receive Segment Coalescing (RSC)
- Allowing users to adjust storage repair speed
- Making storage bus cache available for standalone servers
Meanwhile, Windows Server 2025 improves performance with changes like:
- Block cloning support
- Dev Drive storage volume focused on file system optimizations that improve control over storage volume settings
- Enhanced Log to reduce impact on Storage Replica log implementation
3. Enhanced Efficiency and Agility
As the world migrates to hybrid on-premises and cloud infrastructures, the upgrades to Windows Server follow along. For example, Windows Server 2022 came with new Azure hybrid capabilities with Azure Arc, a way to manage Windows and Linux physical servers and virtual machines hosted outside of Azure to maintain consistency. With Windows Server 2025, the Azure Arc setup Feature-on-Demand is installed by default so adding servers is easier.
Challenges with Windows Server Upgrades
While upgrading Windows Server comes with multiple benefits, you may be concerned about the potential problems and challenges, including:
- Compatibility issues: Applications running on the server may not work with the new OS version, leading to outages.
- Configuration restrictions: Server boot configurations may complicate the upgrade process, requiring reconfiguration or virtualization changes.
- Disk space: Upgrades typically require extra space for installation files and temporary processing or else they fail.
How to Troubleshoot a Windows Server Upgrade
While you want everything to work perfectly, you don’t live in a perfect world. If you have to troubleshoot your Windows Server upgrade, then you might want to consider some of these issues.
Review event logs
Using the Event Viewer, you can scan the System and Application logs for Windows Events generated around the same time you did the upgrade. Some Windows Server error codes include:
- 0x80244007: Windows cannot renew the cookies for the Windows Update
- 0x80072EE2: WIndows Update Agent unable to connect to the update servers or your update source, like Windows Server Update Services (WSUS)
- 0x8024401B: Proxy error leads to Windows Update Agent being unable to connect to update servers or your update source, like WSUS.
- 0x800f0922: Updates for Windows Server 2016 failed to install.
- 0x800706be: Windows Server 2016 cumulative update failed to install and was
- 0x80090322: HTTP service principal name (SPN) registered to another service account so PowerShell unable to connect to a remote server using Windows Remote Management (WinRM)
Check for Pending Reboot
An upgrade typically requires four reboots. After the first reboot, you can expect another within 30 minutes. If you see no progress, the upgrade may have failed.
Review Servicing Stack Updates
The servicing stack updates (SSUs) fix problems with the component that installs the Windows Server updates to make sure they’re reliable. Without the latest SSU installed, you may not be able to install the feature or security updates.
Check CPU and I/O
Since the Windows Server upgrade uses a lot of compute power and disk space, you want to make sure that you check these metrics to make sure the process is progressing.
Check Firewall Service
You may need to have the Windows firewall service running for the updates to work. To check whether the service is running, go to Service Manager>Services>Windows Firewall.
Graylog Enterprise: Faster Troubleshooting
Graylog Enterprise enables you to aggregate, correlate, and analyze all your log data in a single location. With Graylog Extended Log Format (GELF) inputs and BEATS inputs, you have a standardized format across Windows log types
Graylog supports Winlogbeat to ingest Windows event logs directly into our BEATS input, or you can use the NXLog community edition that reads Windows event logs and forwards them in GELF.
Using Graylog Sidecar, you can implement multiple configurations per collector and centrally manage their configurations through the Graylog interface. Graylog Cloud accepts inputs from the Graylog Forwarder so that you can collect the same kind of logs from different parts of your infrastructure or maintain a more redundant setup.
