Is direct in-place upgrade possible from windows 2016 standard to windows 2022 standard.

Hello Rozer S Pacheco, thank you for posting in the Microsoft Q&A community. I understand you are planning to perform an in-place upgrade of your domain-joined Hyper-V VMs from Windows Server 2016 to Windows Server 2022, and you need guidance on prerequisites, backup methods, hardware sizing, and upgrade timelines.

To answer your specific hardware and performance questions, having 50 GB of free space on the C: drive is more than enough. The upgrade process generally requires a minimum of 32 GB of total disk space, but practically needs around 20 GB of free space to accommodate the setup files and the Windows.old rollback folder. As for the 4 GB of RAM, this does meet the Microsoft minimum requirement (2 GB for Server with Desktop Experience). However, 4 GB may cause the upgrade process to run a bit sluggish. If possible, temporarily allocating 8 GB of RAM to the VM before the upgrade will significantly speed up the process, and you can dial it back to 4 GB once the upgrade completes. The upgrade timeframe depends heavily on your Hyper-V host's underlying storage performance (SSD/NVMe vs. HDD), but it typically takes between 45 minutes to 2 hours. Since the upgrade engine primarily processes the C: drive (OS layer), the 100 GB D: drive will not heavily impact the timeframe.

Regarding credentials, initiating the upgrade using the built-in local Administrator account is highly recommended. During the upgrade process, the VM will restart multiple times. If the server temporarily loses network connectivity or domain trust during these reboots, domain credentials might fail to authenticate. Using the local Administrator ensures you securely retain access to the server at all times.

For your backup strategy, relying on a Hyper-V checkpoint is an excellent rollback method, but there is a crucial caveat. Since the VM is domain-joined, you must ensure you take a Production Checkpoint rather than a Standard Checkpoint. Production Checkpoints utilize the Volume Shadow Copy Service (VSS) inside the guest OS to create a data-consistent backup. Standard Checkpoints merely capture memory states, which can cause Active Directory USN rollback issues or a broken domain trust if reverted. For the safest approach, always couple the Production Checkpoint with a full traditional backup using your standard backup software, just in case the virtual hard disk itself becomes corrupted.

Here is the standard and safest process to initiate your upgrade:

1. Ensure the Windows Server 2016 VM is fully patched with the latest Cumulative Updates.
2. Uninstall any third-party Antivirus or EDR software.
3. Take a Production Checkpoint of the VM in Hyper-V Manager.
4. Mount the Windows Server 2022 ISO to the VM.
5. Log in as the local Administrator, open the ISO drive, and execute setup.exe.
6. Select Download updates, drivers and optional features (recommended).
7. Choose the correct Windows Server 2022 edition (Desktop Experience or Server Core) that matches your 2016 deployment.
8. Crucially, select Keep personal files and apps. If this is greyed out, verify you do not have an OS language or edition mismatch.

If you run into any upgrade blocks or rollback errors during your maintenance window, please reply with the specific error code displayed on the screen so we can isolate the issue. Additionally, you can gather the setup logs by running the following command in Command Prompt (Run as Administrator) to retrieve the critical error entries:

findstr /c:"Error" C:\$Windows.~BT\Sources\Panther\setuperr.log

Please share the output of that command or provide the full setuperr.log so we can investigate exactly what blocked the migration.

I will follow up on this thread to ensure your VMs are upgraded successfully. If the guidance provided helped you navigate to this solution, please consider clicking 'Accept answer'. This officially marks the thread as answered and greatly helps other community members who are searching for a solution to this exact same problem.

Official Microsoft Documentation for your reference: Perform an in-place upgrade of Windows Server Hardware requirements for Windows Server

Hi, Rozer,

Yes — you can upgrade directly from Windows Server 2016 Standard → Windows Server 2022 Standard. There’s no requirement to upgrade to 2019 first, and Microsoft includes 2016 → 2022 as a supported in‑place upgrade path.

That said, for environments with many workloads — especially something like your 50 VMs — the recommended approach is different.

Recommended Approach for Stability

A clean install of Windows Server 2022 on a new machine or VM, followed by migrating roles and data, is the safest and most stable method. This avoids carrying over legacy drivers, old components, or configuration issues from 2016.

Why Clean Install Is Better

• Gives you a fresh, fully supported OS baseline

Reduces the risk of upgrade failures

Avoids downtime caused by rollback or corruption

Ensures long‑term stability for production workloads

For a large environment, a phased migration using the clean‑install method is the best way to minimize downtime and risk.

If You Still Choose In‑Place Upgrade

It’s supported — just make sure:

Edition matches (Standard → Standard)

Server is fully patched

Drivers and firmware are updated

You take a full backup and a VMware snapshot before starting

Microsoft Documentation

You can find the official upgrade path reference under: Windows Server upgrade and migration (See the In‑place upgrade section.)

If you want, I can help you plan the migration or outline the safest upgrade sequence for your environment.

Hope this helps, Martin

I look forward to your update and am happy to continue working with you until the issue is resolved. If you find the answer helpful, please click "Accept Answer" and consider upvoting it. Otherwise, please keep me posted by clicking "Add comments" below instead of selecting Yes or No.

This response is drafted with the help of AI systems