Moving from Server 2003 to Server 2025

[Tracey Willis]

My company is a nonprofit and have had a Windows environment for at least 15 years or so. We currently have a Windows Server 2003 (yikes) and day 1 of me taking over the current main IT role, I immediately mentioned to my boss that we need to get something new in place. With that being said, our Server 2003 is a VM that is the main DC and I have 3 other VM's: Print Server, File Server, and Quickbooks that are all hosted on a physical server running ESXi. We ordered a new physical server and Windows Server 2025 Standard. My questions are, since this will be the first time doing this:

1. The VM's are currently in old version of VMware. How can I move these 3 VM's to Hyper-V when I get my new server setup?
2. How do I go about moving Active Directory and roles from the old DC to the new DC?
3. At what point do I demote the old server?
4. Is there a checklist, guide, etc for this because I'm nervous??!!

I appreciate any feedback, just looking to do this the right way with the least amount of issues.

[kasper]

You need to step back and seperate your tasks and questions for the proper support websites.    None of your questions really apply on this one.

[CarltonR]

Not sure that you are necessary have summited this request to the appropriate section of the forum, this is for area is for Workstation questions rather then ESXi.

But, If I get this right you wish to migrate an AD Win 2003 Servers to some shinny new AD Win 2025 Servers, and then move it from ESXi to Hyper-V.

1. The VM's are currently in old version of VMware. How can I move these 3 VM's to Hyper-V ?

If you search for 'Migrate ESXi to Hype-V' you will find many articles on how to perform this [refer Note below]

2. How do I go about moving Active Directory and roles from the old DC to the new DC?

I Would suggest viewing this YouTube video, the process of which I have used successfully in the distant past [refer Note below]

Active Directory Migration from Windows Server 2003 to Windows Server 2016,

Vikas Singh, 29th March 2017,

https://www.youtube.com/watch?v=B7GSRwRQcNc

3. At what point do I demote the old server?

When you are completely happy with the migration [refer Note below]

4. Is there a checklist, guide, etc for this because I'm nervous??!!

Assuming that you have the necessary skill set, then as long as you, backup, test, test and test then you should be able to gain the confidence and create a list of actions required.

Note:

Make sure that you have backups of all your system before doing anything, best practice in any event.

Before attempting this for the live system, clone the three AD Domain Win 2003 Servers VMs and place them in a completely isolated test area.  Create a Win Server 2025 VM instance within this isolated test area (doesn't bother licensing it, just use the grace period, cos the likelihood you will go through this a number of times),   You'll also need a 'users' workstation VM linked to AD.  Then perform a migration, and thoroughly test (suggest creating a list of tests to be performed), repeat until confidant that all is well.

You have a couple of options for the live migration/transfer . . . but would suggest this one; go though a migration in the isolated test area as though you were in the 'live' environment, power down the existing 'live' Win Server 2003 AD servers and make the test area Win 2025 servers live by presenting them to the network.  In doing so, if thing don't quite go to plan then your 'old' Win 2003 Servers are still in tacked and can be brought up again with minimal disruption, and reduces the risk.

Once you are happy with the AD migration, then would suggested going though the Hyper-V migration process, testing it within isolated test area.  One thing that I not sure about, without researching it, is the the ESXi version level that Hyper-V requires.

Clearly the order in which the objectives can be achieved is open to discussion, such as do you do the ESXi AD first then move to Hyper-V; Hyper-V first and then the AD migration; do the both at the same time . . . however, the risks need to be clearly understood and assessed, with the final decision down to the priorities and the risk appetite of the origination.  I prefer managed stability and controlled caution, however as I don't have any knowledge of your infrastructure and origination my choice may differ, I personally would go for the order of migration as suggest above.

[Daniel Casota]

For a non hightech profit org better use a SaaS approach aligned to your business goals. Choose wisely. Pay the bill for data migration, cybersecurity and subscription. Be happy.

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[Technogeezer]

If you've never done this before:

I second @CarltonR in strongly recommending that you create an isolated sandbox environment (including isolated virtual networking) that you can use to perform any of the steps in the migration. You should expect to make mistakes and have to start over. The separate environment is critical to keeping things working while you do the conversion.

You should also expect that this is going to take a while as you learn what works and what doesn't.

If it were me and this setup is critical to the operation of the business, I'd be looking for someone that's done this before to minimize both risk and time.

Also, is there any component of this environment that is running on VMware Workstation? From what you've posted, it appears that everything is running on vSphere/ESXi. If so, I'll ask that this thread gets moved to the vSphere or ESXi communities where you'll have access to more subject experts for that platform.

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- Paul (technogeezer)
vExpert 2025
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[Daniel Casota]

Most importantly, determine who requires access to the inventory and for how long - just internal users, or also customers and suppliers?

My perspective differs from that of other members of the community. Focus on the future needs of your nonprofit rather than starting a migration project right away. If you want to keep using your content, consider a migration and holodeck hosting package for Windows 2003 from a provider experienced with VCF.

Do you think someone unfamiliar with the environment can truly understand the issues of using an old VMware version or explain why a 2003 domain was kept? There may have been valid reasons for a "make" approach, but this poses significant risk for the new IT lead. For non-technical NPOs, such technical projects can strain budgets, and if the system is highly critical, it's unlikely to be managed in depth by NPO internal IT staff.

[kasper]

SaaS at this point is not high on the list given the hardware and software (2025) have already been purchased.   The clients appear to be Windows or possibly something that runs a web browser.   The benefit of keeping AD is the user account and security structure, managing clients through GPO and possibly some other 3rd party software, and possibly printing.   Again, break it all down and go to the approriate communities.   This is not one of them.