In place upgrade of Windows 2012 server to Windows 2022.

Windows 2012 or 2012 R2?

I am pretty sure you'd have to go from 2012 R2 to 2019 first. Then from 2019 to 2022? Could be wrong.

In any case, here's a KB from Microsoft with requirements and best practice:

https://learn.microsoft.com/en-us/windows-server/get-started/perform-in-place-upgrade

Curious - what's driving the decision to upgrade in place vs a clean install and then migrating roles or data?

And are these VMs or physical?

I am pretty sure you'd have to go from 2012 R2 to 2019 first. Then from 2019 to 2022?

correct...you can't jump from 2012 R2 directly to 2022; need to go to 2019 first

In place upgrade of Windows 2012 server to Windows 2022. 

any reason not to do a clean install?  better than risking doing two OS upgrades to get to where you want to be

if you must, make sure you have good backups

What does the server that you think an in place upgrade will maintain?

If it goes throught. you are golden, what happens if even onet hing fails. what is your plan? What is the impact.approach for a remedy? How much time you have to try to recover?
Do you have a known good backup of the 2012 system.

Direct upgrade isn't officially supported. It might work. It may not.

Those servers are ancient. I don't know if 2022 will run on them properly.

Considered age of hardware and OS, this seems like a good time to upgrade the hardware platform to something a little more modern. For the effort and the lifespan, I would look at at least a 14th gen Dell server. The Dell 13th gen servers at at max ESXi 7, which goes EOL in early 2025, so not even worth migrating to at this point. That's why I suggest at least 14th generation server.

I also recommend deploying as VMs going forward. Makes upgrading OS, migrating to new hardware, and overall recoverability much easier.

there is an official Dell guide on this matter - upgrading to Windows 2022 on Dell PowerEdge Servers. see below.

https://www.dell.com/support/manuals/microsoft-windows-server-2022/win2022_ig_pub/install-windows-server-2022-by-using-operating-system-media

Thanks to all responded to my query.   It appears that in-place upgrade is more of a gamble that anything else and cannot afford downtime per se.   To @arnold's question, yes I do have a full backups retained for 4 months and is recoverable in 6-8 hours time.   One of the servers is mainly used as a file server but the 2nd one has an accounting software integrated with our customer solution hosted in an Azure environment.  Third one is a UAT server, where users test our custom solution integrate with the accounting package.   This server is not critical in the pipeline.   In general, I am getting the feeling that in-place upgrade is not a good idea :-(.

www.experts-exchange.com/dashboard/#/questions/29262838?anchorAnswerId=43551036 

@bbao, I did not see any reference to in-place upgrade on Dell servers in the above link.   Did I miss something?

The newer systems are more granularity handling roles and features.
Someone recently posted on EE who had a 2012 RRAS/VPN /nps that they tried to in-place upgrade, which did not go as planned.

Virtualization is likely a path to pursue.

Depends on do you buy new HW, or previously owned.

You could consolidate the three, during an upgrade two two equally powered to include redundancies.

The accounting software relies on MS sql as the backend ..

Virtualization will enable more testing resources ..

...but the 2nd one has an accounting software integrated with our customer solution hosted in an Azure environment

you should check with the vendor if the accounting software is supported with server 2022

@Arnold - we did consider virtualization and is still in play.   Our leadership is concerned about leaving accounting information in the Cloud per se.   Working through it.

@Seth Simmons - Yes, the vendor has an 2022 approved version of the accounting software.

Virtualization can be on-site, it does not mean it is in the cloud.
i.e. hyper-v role with a Fileserver, Accounting hosting server virtualized.

This might be a great opportunity to test.
If you have hardware available for testing to deploy hyper-v host.
or
Add a hyper-v role to a workstation. setup to VMs fileserver and accounting server as though you are starting from scratch, unlikely to accomodate the current live environment.
note you can not test the resposiveness of the vservers while you are running the app on the host, deals with how the host will schedule/allocated its resources between host apps and hyper-v allocated.

another Workstation that has the newer accounting client/pointing to this virutal server setup might be a different thing.

@arnold, I will have to spent some time on this as I am not too familiar but will try.   Thank you.

A related question - can anyone provide guidelines as to how to setup a virtual server in Azure environment and be able to map a drive to it from our local network.  I truly do not have any experience in doing it but willing to give it a try.   The goal is to replace the mapped drive behind the scenes so users won't notice any change.

Do you have a VPN connection setup between your environment and your Azure Server?
That should be the step you take.
once they are connected via VPN, they are within the same AD/AAD linkage?

DFS?

I think you were looking to link users to their oneDrive Business ....

the o365 includes a "sharepoint" like environment.
documents shared within the organization, groups of people....

@arnold, I haven't started any setup yet.   Trying to find the steps involved.

To have file sharing, you would need a VPN connection.
https://techcommunity.microsoft.com/t5/itops-talk-blog/step-by-step-creating-an-azure-point-to-site-vpn/ba-p/326264

You should treat a cloud deployment as though you were using another branch, Data center location etc. same rules apply.

how to secure communication from Location A to Location B.

Are you currently using Sync to get your AD info sync up to the AAD?

Mapped drive to a server in Azure would require site to site VPN, and may cause performance issues due to WAN latency. Given what appears to be organization's comfort and ability to implement technological change, I do not recommend putting file server in Azure while keeping users local on prem.

@arnold, our local AD is not linked with AAD.   I have done site2site VPN for our custom solution, so aware of that procedure.  Thanks.

@kevinhsieh, I can do site2site VPN, no issue but latency is a concern.   Thanks for the note.

How intensive a reliance onshared files is?

If the two are not in sync. How are the user credentials will be recognized, handled for file access?

What are the commonly used apps? Office, custom solution?

@arnold, for one division, they just use office apps (Outlook, Word, Excel etc.) but the other division has an accounting package integrated with a customer solution hosted in an Azure instance but managed by a third party.

Tye accounting tie in is it a web based access which should not be impacted bythe move.
If it is a windows client type that does SQL style queries or needs fileshare access akin to quickbooks, that woulhave to take kevin's suggestions
I.e. RDS or vdi style hosted in the cloud.

@arnold, thank you for the notes.   We use Sage - PeachTree - users inhouse uses windows client but the customer software is integrated via APIs.

Well, you have to test latency over the VPN and how many transactions it needs to render the view ...

It might be better to use RDS to publish the accounting applications to the users who need it.
All activity related to the accounting group will be within the cloud. The overhead might require a change in the package...

Testing is likely your best approach. i.e. setup the a test copy of the data, and a workstation that targets the remote, then have someone from accounting run through the normal things, lookup, etc. to gauge how responsive it is noting that it is one user at a time.

So you RDP to the virtual server, install the app and have users test it.   I got that part but would server allow 'vanilla' users login to it?  I don't any experience with VMs, that's why I am asking.

looking at your response, my response seems to have combined several different other question into this one.
First thing first,
The approach from your vantage point is the same as if the server was physical sitting in a room.
a VM, simply, instead of going into a server room, you connect to the Host that functionally is the virtual Server room where all your (VM) servers are.

You would follow the same procedures you have when you are testing an upgrade of servers.
1) Install the OS, name the server, setup on the network, join to the domain, install applications
2) have a workstation from which you configure the applications to target the new server as the data respoitory.
3) run the applicaiton and see how it goes.

The host specification is what you would need:
how many VMs do you need?
To simplify to fit the Virtual Environment into what you already know is If you are going through an upgrade cycle, how many servers do you need? This will answer how many VMs do you need. (Standard OS comes with 2VM entitlement, Datacenter OS version has unlimited VMs, as many as the Host's resources can handle)
How much space does each server need to handle over the subsequent 5 years, before the next upgrade cycle.
This deals with the amount of storage your Host server will need to account for.

I think there are times, trying it out by adding the hyper-v role to a workstation, setup a minimal windows2022 server as a VM will do more quickly to answer many of the questions  that you might have after reading this comment than this exchange.
 

As I mentioned earlier all VM World is new to me so trying to digest.   I need one app server where the accounting software would run.   The other one is a plain/vanilla server to use simply as a file system.   The third one will be my test/UAT server, I can wait on this.

Based on your comments, I think the following may be the steps I should take.

1. Create a VM server in Azure

2. Add the server to our domain

3. Install the accounting software

4. Map necessary drives to the VM

5. Have users test

Does this sounds right?

I am trying to reduce reliance of the local resources.   Hence thought of going VM on the Cloud.   Isn't that a reasonable thinking?

If you have local resources that depend on a cloud resource, or vice versa, that just complicates things and makes it more fragile than having all VMs in a single host or single site.

@kevinhsieh, may be I should start thinking of just using VM instances for everything and local network just for printing/scanning etc.   All users needs to RDP to the virtual server to do their work whether using the instance as a file server or as an app server.   Do you all suggest installing Office apps on the VM server?   I know in the past (for on-prem instances) that was a big no.   Has this thought process changed?

If the Users are on O365 they have office entitlements.
You would not need to install office on all VMs.

If you are placing Servers in the Cloud, VMs.
An RDS server in the cloud would make more sense the RDS will reduce the complexity of accessign Cloud stored files.
You could use the AAD's two factor auth

 it will reduce the quality of Workstations needed as the load will be born by the Cloud infrastructure and the local workstations will provide, function as dummy terminals to the RDS server.
https://learn.microsoft.com/en-us/windows-server/remote/remote-desktop-services/rds-plan-mfa
https://learn.microsoft.com/en-us/azure/active-directory/fundamentals/auth-remote-desktop-gateway

https://learn.microsoft.com/en-us/azure/active-directory-domain-services/secure-remote-vm-access

Can you use the old server with Eval win2k19/22 as a hyper-v host? to experiment with VM setups?

@arnold, not really :-)   They are all in active use status.

If you have a Cloud test tier, you could try testing setting up, VMs installing apps, and testing interactions there.

@arnold, you read my mind - signing up for a free tier w/Azure.   Have to dedicate sometime this afternoon to go through.   Thanks.

Why would you need Office on a file server? File servers normally would only have AV software installed. In fact, better practice is to have file servers be running Windows Core no limited ability to run GUI software.

Office would be installed on RDS Session Host (terminal server), which would also have accounting software installed. Users would RDP to this server, and then do their work.

@arnold, so in addition to having a VM server to host all the user files, you are suggesting to add a Terminal Server with apps so that users can login to the TS and then access the files on the VM server.   I have to try all these out - ours is a 1 IT man show.

VM doesn't mean something has to be in the cloud. VM just means that how you provision operating systems on hardware is different. IMHO you should run everything as a VM. Microsoft allows 2 Windows Server Standard VMs to run under a single license on a piece of hardware. You can run 3-4 VMs on a server for the price of two Windows licenses, a savings of 33% over the price of the three licenses you need now, and you get to run 33% more Windows VMs than you could bare metal. More installs at less cost. Plus a ton of other benefits, like snapshots, ease of migration to new hardware, speed of deployment of new VMs vs purchasing new hardware, save on hardware, etc.

My recommendation is a single server to run all VMs needed, such as domain controllers, file servers, application servers, RDS Session Hosts (terminal servers), database servers, test environments, etc.

Kevin Kindly covered the aspects you raised.

I may have been participating in two similar questions (dealing with OS transitions, one had a server with storage issues) which merged some suggestions into this question.

Currently, do you ave any application redundancy file server (dfs replication) two DCs/DHCP/DNS?

You currently have three hW servers.
as Kevin pointed out, provided the storage resources are there, each server's current utilization is likely between 25-35% the rest of the time it is sitting idle during business hours?
running two VMS on the same hardware, will get the same server to 35-50% utilization during the same time frame. i.e. if you have a VM that is the Sql server and the AD/dc/DHCP/DNS fileserver the SQL server as an example. The AD/DC/DHCP/DNS/Fileserver is not a large CPU/Memory consumer... as compared to the SQL server.