currently I am migrating a Server 2008 32-bit standard server to Windows Server 2012-R2 64 bit. The server is their only server that runs everything. Its for a client who runs a dental office so they have all sorts of shares and fun dental software. The trickiest part is getting software to work etc. but I was wondering if there are any tools or checklists that can help me in this process? For example I was going to do everything manually, by writing down what user roles they have, what software is installed, what network shares are active. I then realized there HAS to be a simpler way, but I'm a newb network admin. Are there any tools to gather information about all the things I'll need to migrate or perhaps a checklist of sorts and I can reference to make sure I have gathered the information? I'm focused on figuring out how i'm going to get their old software including SQL 2005 running so I don't want to miss something simple like a network share or user group. Thankyou very much!
The smoothest way to do something like this is piecemeal which requires having a second set of hardware to migrate things to one by one. Start with the obvious apps/services and continue until there doesn't appear to be anything left. Then plan a window where you shut down the old server and see if anyone screams. Fix/move the things they screamed about. Rinse and repeat.
Depending on the app/service, you may be able to temporarily run a copy of it on both servers and just migrate a few test users before you migrate everyone. Given the size of something like a dental office, that might be more trouble than it's worth though.
Do your future self a favor and document everything as you migrate. What data needs to be backed up? Where is it located? Is it backed up off site or in the cloud? What client settings need to be configured?
There are PowerShell cmdlets like
Get-WindowsFeature
andGet-SmbShare
that can enumerate things like shares and built-in roles. But there's nothing that's going to reliably pick up any and all 3rd party software. The contents of thePrograms and Features
UI will give a decent list, but won't show anything that didn't actually "install" in a normal sense. There are tools like Process Explorer that can give you a more detailed view of what's running, where it's running from, and what files/handles it has open. AutoRuns can tell you what is configured to run on startup/login.