Guide to Unattended Windows Server 2025 Preview Edition Installation: Simplify Your Setup

Edition: Saturday, March 23rd, 2024

Today I want to share a quick tip on getting started with Windows Server 2025 Standard Edition (preview).  It seems Server 2022 just came out a few short weeks ago but in reality, it was released on August 18, 2021. 

As technologists, we sometimes delay the inevitable, upgrades.  Mostly this is due to not having the bandwidth and environment to certify the new version supports our business applications.  This usually involves tediously tracking down dependencies and working with outside vendors. 

Internally, we struggle to get buy-in from application stakeholders to test.  We even begin to wonder if looking at the latest and greatest OS version is worth it; until before you know it, extended support has ended and you're no longer receiving critical security patches. 

Now you're scrambling.  Scrambling to plan the upgrade and stay in compliance (SOC2, PCI,  and many others).

I've been through this issue a few times.  First with Windows Server 2003, then again with Server 2008.  Here's how it usually goes:

• You - Notify the business stakeholders that a particular application is running on Windows Server 2022.  Mainstream support ends on October 13, 2026.  What are the plans for moving the application?
• Application owner - No plans yet, October 13, 2026, is over 2 years away.  We need you to focus on releasing new updates and capabilities for the application.
• You - Wondering if now is the best time to begin looking into the next version of Windows Server.  You decide not to and continue supporting the business.
• 2.5 short years passed and no one has looked into the new OS or knows if the application can support it.  You start scrambling and need to set up a test environment and answer the following questions:
  • What new features are available?
  • What was deprecated in the now almost 2-year-old "new" OS?
  • Will the application be supported?
  • Will it perform?

Thankfully, we can address a few of these problems by setting up Windows Server 2025 (preview) today.  This allows you to begin your review ahead of schedule in a self-paced manner.  I've set up a Windows Server 2025 virtual machine to begin testing the following (some of which have been answered):

• Can I automate the installation using an autounattend.xml file?  Yes, you can too.  Instructions and a quick video are below.
• Are there any changes with WinRM remoting that I need to be concerned about? 
• Do my existing Ansible playbooks work?
• Should I begin using OpenSSH instead of WinRM?  FYI, OpenSSH server is installed by default in the latest preview.
• Does it work well with ISCSI storage? Yes, so far.
• SQL Server 2022 - Single instances, FCIs, AGs, Replication
• What new features can I take advantage of?
• Do any of the Hashicorp Packer or Vagrant files I built for the Automated Sandbox Fundamentals course need to be updated to support this OS?  Yes, minor changes are required but this build will be included in the next version of this course.

I'm sure there are still many changes coming once 2025 releases.  Here are a few of the new features:  

• Active Directory Domain Services
• Azure Arc
• Bluetooth
• Desktop Shell
• Delegated Managed Service Account
• Email & accounts
• File Compression
• Service Message Block (SMB)
• Windows Local Administrator Password Solution (LAPS)

You can find the details of all changes here.  Also, check out last year's Ignite session for additional information.

No one wants to sit through the installation and click next, next, next etc (boring).  

Let me show you how you can perform an unattended install quickly on VMware Workstation Pro.  If you need to see the process of building an autounattend.xml file, check out How to create Windows Answer Files for Unattended Installations (automatesql.com) for instructions.  This post shows how to build one using Windows Server 2022 but it's the same process for 2025 with one caveat (2025 preview requires a license key).  If you already know how to build one, I provide the link below to the one I use.

Windows Insider Program

The first step is to download the ISO.  To do that, you'll need to sign up for the Windows Insider Program for Windows Server.  Sign up here. 

I used the ISO, the first option in the drop-down, vs downloading the VHDX file. But you have multiple choices. 

Building the Autounattend file

Fortunately, I reused the file I had built for the Windows Server 2022 Evaluation edition.  It did require a license key to be added (find those here).  This specific file will perform the following as is:

1. Installs Windows Server 2025 Standard Desktop Experience
2. Sets the computer name to packer-win2025.
3. Sets the Administrator password to packer.
4. Enables autologin.
5. All locales and languages are set to en-us.
6. The timezone is set to Central Standard Time.
7. Disables Server Manager from opening at logon.
8. Multiple PowerShell statements enable Winrm (remoting).  A self-signed certificate is created to support Winrm over https.
9. Firewall rules are added to enable connectivity over ports 5985 and 5986.  I added these to support the use of Hashicorp Packer, Vagrant, and Ansible.  

The example can be downloaded from here.  Be sure to save the file as autounattend.xml before placing it on a floppy (or virtual floppy).  

Here's a quick video to see it in action with VMware Workstation Pro (10 minutes 27 seconds).

https://youtu.be/rV8z6gxKxJ0

Conclusion

I'm not saying you need to jump to Windows Server 2025 as soon as it's released.  But, you should be aware and familiar with the changes it introduces long before mainstream support for Windows Server 2022 ends.

Don't let 2025 sneak up on you.  As DBAs and IT technologists, it's paramount that we help lead the businesses we support into the future.  With AI becoming ever more prevalent, I believe we'll see an explosion of exploits being discovered.  Staying current, with a supported OS, will be extremely important to ensure you're receiving the latest security updates as those exploits are uncovered.  

That's it for today.  Have a great week!

p.s.  Boot time for the current preview is insanely fast.  13 seconds in my environment.  I don't believe I've ever seen a Windows OS boot that fast.