If you can get the organization to switch to Debian, you could do it all with free software and manage the whole thing with Ansible.
I mention this because if the org is running Windows software that old, then current generation FOSS software is going to be a breathe of fresh air, by comparison.
It might not work if someone with a C title has a specific magical Windows package they want.
But even then, I would manage one or two Windows PCs (for a couple of C suite execs) by hand, than a full organization full. And you would save the organization a boatload of money.
There are multitude of OS & software in running. Some people still use DOS, but most of those were already upgraded - to windows XP. These machines are currently being replaced with Win10 ones. But due to some specific old SW there still need to be some DOS machines running, at least for couple upcoming years. Linux is sadly not an option for typical office workers, again due to some software in use. There's at least open source in places where possible with more (Firefox, Thunderbird, tightVNC, ...) or less (LibreOffice) success.
I haven't tried, but given how quirky it is (in house development decades ago with patches and hotfixes stuck to it over years) I highly doubt it would work. The main problem is that there's no will to use Linux in office environment...
We're at least running it on POS machines - about 150 openSUSE installs - where there's nothing fancy needed.
DOSBox runs on both Linux and Windows (and probably Mac too?); I was suggesting it since you might be able to replace the dying DOS computers with a modern system and just launch the legacy system as an application under it. (You might be able to do the same with a VM as well, but DOSBox came to mind first and may be easier to setup and distribute.)
Just a thought. If it's not useful, feel free to disregard.
I haven't tried to run DOS on Win10, but I haven't been able to get my old DOS programs to run on anything Windows XP or newer, myself. XP at least had some compatibility options to try. I don't think I've seen those options in Win7 or newer.
It will vary by program, but I've needed DosBox on Windows, as well as on Linux, for anything DOS based that I have run anytime recently.
How to learn Windows? Years of pain and torture of course.
What to learn? Powershell, learn powershell.
Then as you follow along any guides or howtos for administrative tasks, try to search how to accomplish the same things in powershell. Take notes on your own powershell learnings. I keep all my windows administrative powershell one liners, scripts, and notes in the same digital notebook for quick reference and updating.
If you're already experienced with bash, like I was, learning powershell might be tough. As it was for me, I had trouble understanding why PS cmdlets seemed to hide data when piped... Format-table(ft) and Format-List(fl) help tremendously
Powershell remoting is still a pain in my ass in most places, I rarely use it.
YouTube! Don't necessarily look for YouTube powershell windows videos. Just the necessary tasks through the GUI will give you the correct direction to begin converting a process to PS. Learn how other Admins process tasks by watching them. Especially if it's an often repeated task try converting some or all of what they do in the video into PS equivalent.
With all of that said knowing powershell doesn't really help recovering from disasters. Knowing how to install windows and recover data from borked systems is a task best learned through battles. So, absolutely set up VMs and installed all manner of versions you'll be working with...that way you'll have familiarity with when things go wrong in them. I've yet to install windows 11 in a VM but I did try to install a copy onto a surface tablet only to learn the hard way that do ing so leaves the tablet without the drivers necessary for using the keyboard and touchscreen...weird need a custom built image or recovery image, great fun.
I may only use VMware workstation pro for desktop virtualization for lab use, and I do realize the ramifications for enterprise operations are exponentially greater. But even I am getting a worse service. I used to be able to google an issue, find a link to the VMware forum and just open that. Now *.vmware.com redirects to broadcom.com and searching for the post there seldom finds it again. Absolutely brilliant timing for google to kill cached pages.
Hyperv has shit automation support and doesn't provide native apis to work with. You need vmm or some third layer to talk to. That's where the shit starts
From an admin perspective one of the best things to lab out is setting up a standard SMB server stack, which is 2x domain controllers, 2x DHCP servers, a file server, and a couple of desktop VMs, then practice setting it up to be nicely locked down like in a standard corporate environment. For example:
redirect user directories to the file server and set permissions so only the user, admins and departmental managers can access files
setup departmental directories on the share with departmental and managerial permissions
setup group policies to lock down the desktops so that users just get a standard experience
But also make sure to set this up both in Windows Server with the full "Desktop Experience" as well as on Windows Server Core, and try to do so while following best practices with redundancy, network segmentation, etc. you could even get fancy and setup a remote site with redundant servers and replication to the remote site as well to experiment with how that works.
Then of course, once you have your virtual SMB network setup, try to break it. Fill up some of the VMs so it's out of disk space, corrupt one of the VMs and try to recover it, power off the servers when you shouldn't, cut some important virtual Ethernet connections and leave them severed for a while, or degrade the virtual ethernet connection and see what happens, delete the only domain controller and see what the best path to business continuity is, etc.
This covers a lot of the tickets and critical failures you'll see on a standard SMB network and will give you a good amount of exposure to a lot of what you'll work with in the "real world"
You can basically get rack mount level performance from:
Supermicro SuperWorkstation Tower Servers
Lenovo Thinkstation P Series Server Towers
HPE ML series Tower Servers
Dell Precision Tower Workstations
In your situation, I'd be looking at ebay, serversupply, or other used hardware resalers that offer 2 generations back hardware. Used DDR4 based systems are abundant and cheap enough, go that route.
Your use case sounds like something a nuc or sff from minisforum could handle, but if you want "cheap" and "small enterprise," both ambiguous terms, the supermicro superservers should fit the bill.
You're going to need to be more specific about your use case, because if you say "enterprise grade" I'm going to say "poweredge", and those are not at all small.
I know. I felt while writing the post that this feels wrong writing those words in same sentence.
The scenario is that we would deploy the hardware on customer premises so it has to be supported and very reliable(hence enterprise grade).
But i personally think that all enterprise grade hardware is way overkill for running ansible playbooks. So was trying to see if there is an intersection point between these opposite requirements.
Check out NetBox. It is a free open source datacenter inventory management and IP address management tool. It will let you catalog all of your physical assets along with the network assignments.
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