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I seem to have bitten off more than I can chew, and I need help.

I'm inexperienced with windows server. My boss even more so. I've successfully planned and deployed a domain server from scratch before and I'm doing my best to learn as I go, but you should assume I'm a moron.

The company I work for has an aging 2012 R2 server that is rapidly dying. My boss wants me to move it to the shiny new hardware we bought. The old server is not virtualized, and whoever set it up is long gone from the company.

Immobile requirements from my boss:

1) The new server must be on Windows server 2016

2) SQL must be upgraded from 2012 to 2017

3) New server must be 'plug and play'. Our VPN users shouldn't have to reconfigure anything. IIS must still be live as if nothing went down etc.

4) Hiring a third party is not an option. (We're non-profit and poor)

I absolutely don't have the experience to reconfigure everything from scratch. So my plan was to image the old machine onto the new one, then upgrade the pieces the boss needs me to.

Problem is, I can't run Sysprep without possibly taking the old server down for good. Thus the image I captured still has the old hardware information on it, so some of my drivers on the new machine are borked. Running sysprep after imaging new machine fails. Reinstalling the broken drivers fails. (removing the old drivers and reinstalling the new ones using the provided drivers from the vendor)

I've tried to research methods to migrate servers but all of them seem to have some major reconfiguration requirements, and any configuring from me is liable to break something. I really need a way to "copy all of server A to server B" without anything breaking. I'm about 3 weeks into this and I'm exhausted.

I'm sure I sound like I expect y'all to do everything for me, I swear I've tried to do my homework on this, I've been reading the reference books I bought and googling the hell out of everything, but I'm still underwater, any help would be greatly appreciated.

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The solution is to convert the physical server to a virtual server, not to image it.

Use the "shiny new hardware" as a virtualization host, not as a standalone physical server.

Both Microsoft and VMware have tools to convert a physical server to a virtual server that will deal with the hardware-specific driver issues for you. Imaging the server is going to leave you with those hardware drivers unless the imaging tool is specifically engineered to convert a physical server to a virtual server.

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