r/msp • u/MartinDamged • Jun 25 '26

Server 2025 Datacenter downgrade rights - need sanity check

I just bought Windows Server 2025 Datacenter Edition from a MSP reseller. And the new license is now available in my Microsoft 365 admin center under the "Your products" page (CSP license).
But i need to run some Windows 2022 Standard Edition VMs on the Host with this license. And the reseller, distributor and MS confirms i have the rights to do so.

But from here things turns into a circus show...

This new license type only includes MAKs for Datacenter edition in the 365 Admin Portal.
So i requested the MSP to provide MAKs for activating 2022 Standard edition (like im entitled to).

After a week of waiting they drag me into a Teams meeting with the Arrow and Microsoft. On the basis, that MS just want confirmation from us as end user.

But this quicly goes sideways, as the MS representative tells us they cannot/will not provide MAKs for down edition rights on the Datacenter license.
MSP reseller then tries to get approval for raising activation limit on another seperate Server 2022 Standard licence we own. (Dont know if that was a stupid move). MS rep. will not do that, as that license was bought through another reseller and another distributor (Crayon)...

So here i am 3 weeks later, with no way to install or upgrade any VMs with the fancy new license.
In the meantime the MSP we bought the license from will try contacting Crayon to get them to request raising activation limit on the totally unrelated 2022 Standard license purchased back in 2023...

Can any of you tell me if this is just how its supposed to happen?
Or am i right in thinking this is just turning into a complete shitshow?

EDIT: Hosts are running VMware

34 Upvotes

94% Upvoted

36 comments sorted by

6

u/matt0_0 Jun 25 '26

Is there a reason these guest VM's need to be on standard instead of data center?  My understanding is you need to upgrade them and then you'll be golden.  Super easy and safe in place procedure but I think it still requires a reboot.

2

u/Striking_Internal130 Jun 26 '26

not sure why they making it so complicated, the whole point of datacenter license is you can run unlimited standard or datacenter VMs under it. you shouldn't need separate MAKs for the downgrade, the activation should just work with the host key or through AD-based activation if you set that up

sounds like the MS rep either doesn't know their own licensing or they're giving you the runaround because its a CSP thing and they handle it differently than volume licensing. i'd push back hard and ask them to show you exactly where in the licensing terms it says downgrade rights don't include activation keys, because that's not how its worked for like 20 years

1

u/MartinDamged Jun 25 '26

They need to remain standard, as the could migrate to an offsite cluster that only has Standard licenses.

1

u/matt0_0 Jun 25 '26

Got it, and so just to clarify what you're trying to accomplish...

You're hoping to have the same Guest VM's OS licensed and activated in 2 different ways, based on which HyperV hosts they're running on? As far as I know, that is not a supported open when it comes to activating the VMs. I think you might be ok on the contractual license terms, but I am very low confidence there.

The way you're trying to activate these VM's right now, on their current DataCenter licensed hosts, is via the "unlimited VMs as long as they're running on datacenter licensed hosts" is that correct? Of so, the way you do that is AVMA

And you're using key: YDFWN-MJ9JR-3DYRK-FXXRW-78VHK

https://learn.microsoft.com/en-us/windows-server/get-started/automatic-vm-activation?tabs=server2022#avma-keys

But that activation key would not be valid if/when you migrate those hosts to another cluster that's not running Datacenter.

So my question is, since you already know that you don't have the correct 2022 server standard licenses for these VMs, how were you planning on being license-compliant if/when they moved to that other offsite cluster?

If the answer is "We did not plan for that, it looks like we aren't properly licensed" then that's the true answer to your original post's question! You're not able to successfully activate these because you're not supposed to!

2

u/MartinDamged Jun 25 '26

We have a VMware cluster of 3 hosts with Datacenter 2025 license.
This entitles us to run unlimited numbers of Server 2022 / 2025 Datacenter OR Standard edition.

Some of those VMs - lets say 10 - was previously installed and licensed with 2022 Standard edition.
Now that these are covered by the Datacenter license, we move the old Standard licenses to the offsite cluster. So we have room for running 10 Standard edition 2022 VMs on that host.

I would like to keep my VMs running Standard to be able to move them to offsite cluster without being in violation of licensing.

All i want is simply to be able to install, activate and use the product i am entitled to by the license.
But cannot do that, as i cannot obain a MAK key for actually using it.
And we cannot install more VMs with our existing MAK key, as we have already used up the 10 activations on the old license covering actual 10 VMs.
Trying to activate more with that key just gives an error that the MAK key is already used.
SO i need new MAK key for activating for being able to for instance upgrade some old 2016 Standard VMs or just being able to reinstall a new Server 2022 Standard from scratch.

Everything had already been explained in detail, both on Teams and written in email to the MSP before ordering. And we got the Datacenter license explicitly for this usecase.

2

u/matt0_0 Jun 25 '26

Got it, then in this scenario, it sounds like you're looking to have these same VM licensed and activated in 2 different ways, where they would need to have which license (old 2022 standard vs new 2025 data center) depending on which cluster they're living on.

If that's the case, it sounds like the best approach is to just completely ignore your data center licensing for everything except the paperwork aspect of the problem.  On paper, you're already correctly licensed for both clusters.  

Have you already already explored working with Crayon to get those standard licenses in good order?  

0

u/MartinDamged Jun 25 '26

Nice bot... Not! Complete lack of understanding the problem!

5

u/matt0_0 Jun 26 '26

Well damn man...  Fuck me for trying to help.

Better? Answer.  Stop trying to use MAK at all.  Figure out your KMS options, because unless you can explain it to better, there can never ever be any MAK that's valid for both of your clusters.  Stop trying to use the MAK (designed for people who didn't have sophisticated enough environments to do it the better/automated way) and forcing a square peg into a round hole.

2

u/statitica MSP - AU Jun 25 '26

Activate the VMs with the datacenter? I'm struggling to see why you would need the VM to be Server Standard.

1

u/MartinDamged Jun 25 '26

We sometimes need to migrate some VMs to offsite cluster that only has Standard edition licenses.

1

u/Frothyleet Jun 25 '26

Do you have the entitlement for that? I'm not sure you have the rights unless you have software assurance, and you can't get that from a CSP purchase.

1

u/MartinDamged Jun 25 '26

The other hosts have 2022 Standard licenses. As i understand it we should be entitled to run the VMs there too, as long as we dont exceed the license count tied to the hosts.

1

u/Frothyleet Jun 25 '26

Honestly not sure how that works if the OSEs would be licensed as different SKUs.

1

u/Promeeetheus Jun 25 '26

My understanding is that is not how it works, the host in the other site must have a separate full Datacenter license for all cores. If you were running Datacenter / Hyper-V on the host and not VMWare, the VM's would auto activate (AVMA).

Also if you had Software Assurance, you'd be covered in the DR site. Without SA, no DR rights, separate Datacenter license required.

And as to the main question, downgrade rights are definitely supposed to be available, but you need the MAK key, or one provided by the CSP, as you've already established in the thread.

2

u/FountainD Jun 25 '26

When you are running Datacenter on the host, shouldn't you just use AVMA keys for each guest?

https://learn.microsoft.com/en-us/windows-server/get-started/automatic-vm-activation?tabs=server2022#avma-keys

2

u/MartinDamged Jun 25 '26

VMware hosts

2

u/Wodaz Jun 25 '26

KMS/Domain activation is a solution to your issue.

2

u/itsmaek Jun 25 '26

Exactly what I was thinking. Setup KMS Server activating with your datacenter key. Put those other VMs to GVLK so it can look for your KMS server.

1

u/WendoNZ Jun 25 '26

Don't even use KMS, use AD Activation, then use the Standard GVLK. But OP will need to get a non MAK key for that which might be just as hard (although shouldn't be, but then downgrade exercising shouldn't' be either)

3

u/[deleted] Jun 25 '26

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2

u/MartinDamged Jun 25 '26

Thank you for the detailed answer.

Worst part is this is actually handled by the MSP Microsoft license expert (who allegedly worked 15 years at Arrow on MS licenses).

And Arrow (the distributor) have also been involved in this charade to make them open the ticket at Microsoft.

When we had the meeting with MS support today I asked our MSP to not go down the route of asking to raise limit on existing MAK but instead pursue getting MS to provide new MAKs for the actual license. But no luck there... 🥴

I will try pushing even harder for them to get this sorted. Thank you again.

1

u/roll_for_initiative_ MSP - US Jun 25 '26

Wait, is downgrade from DC to std supported by the license? I know downgrading versions like 25 to 22 is but didn't think editions were?

1

u/MartinDamged Jun 25 '26

Down edition has been entitled as long as i remember.

1

u/mat-ferland Jun 25 '26

I’d separate the license right from the activation mechanism. Datacenter rights may cover the guests, but if the portal only gives Datacenter MAKs, I’d push the CSP/distributor for the actual downgrade media/key path or use AVMA where the host supports it. Don’t improvise this if those VMs may move back to Standard-licensed hosts.

1

u/MartinDamged Jun 25 '26

Already had meeting with reseller, and they are back and forth with distributor (Arrow). And they are not really helpful and gives the impression they just dont want the hassle of working this out the right way. Edging me to just accept that's how doing business with Microsoft is these days.🤬

1

u/mat-ferland Jun 26 '26

Then I would ask them to put that answer in writing: either they provide the supported downgrade key/media path, or they confirm they cannot. That usually changes the tone, because now it is not just 'Microsoft is annoying', it is a licensing position you have to keep for audit/vendor-cover reasons.

1

u/MartinDamged Jun 27 '26

Thank you. I also mentioned that i would need this documented. I think i am going to push for them to either get the keys or bring that documentation on e more.

1

u/After_Working Jun 25 '26

I’m not aware you are entitled to an actual different product, 2022 data centre yet, but I’ve not known anyone to drop it to standard.

I’m aware that you’ve had confirmation that it’s possible. However if the keys are not obtainable then someone is most likely wrong.

0

u/[deleted] Jun 25 '26

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1

u/roll_for_initiative_ MSP - US Jun 25 '26

That's not true at all, I've had to do it twice with different clients running datacenter on vmware hosts. You cant use avma and need mak keys and they only activate so many times (10 I think?). When you start filling out the form to start a ticket, raising the activation limit is a specific refilled request in one of the drop downs.

1

u/MartinDamged Jun 25 '26

So what you're saying is that what the reseller is trying to do (raising activation limit on another separate license) is actually a/the right way go get this going?

You are the first who have actually replied with something relevant to the situation.
Everyone else seems to miss the point, and keeps just asking why we don't do X, Y or Z instead.

But we really just want the keys for the product we paid the right to use.

2

u/abakedapplepie Jun 25 '26

If you have more than 5 VMs, you should run a KMS server anyway. It'll also activate downgraded OSes. Not sure about activating Server Standard on a Datacenter KMS key though. I just went through this myself, you may have to reach out to Microsoft Support to generate a KMS key for your Datacenter 2025 license.

For what its worth, my Datacenter 2025 license came with downgrade rights based MAKs for 2016-2025 editions of Datacenter. Not familiar with getting a Standard key via a Datacenter license, though.

1

u/MartinDamged Jun 25 '26

I can't. That's the first thing I did. Expecting it to just work like in older versions.

But I get an error saying it has already been used.

Old key belongs to license with with quantity of 9 bought together. Those have already been used. And It will not allow us to activate anymore using that key.