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I have a small setup of around ~30 computers [some of which are located at a remote office] that I need to get migrated over from a workgroup to a domain to maintain my sanity. The previous admin didn't mind managing things this way, but keeping track of specific passwords, etc for various machines is driving me insane.

Anyway, we have a fileserver running Windows Server 2008 R2 Standard. With the current setup each person has their username/password for their workstation, and a matching username/password on the server for permissions to different shares, etc. We don't run much of anything special, people just need to be able to access their shares.

My main question is this: If I deploy Active Directory on the server [making it the domain controller] will it be possible for the computers that are still using workgroup settings with their local workstation + local server accounts to continue to function in the same manner until I get that workstation migrated to the domain? Especially considering the remote office [in another state and no on-staff IT guy] I don't want to try to get AD going and run into a situation where nobody can get anything done.

Sootah
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Yes. You can access files if you know the username / password of the server. So the workstations can temporarily stay outside the domain until you migrate them.

TomTom
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I've actually done this with ~5000 computers, but I had power tools (Altiris Deployment Solution). You should have no problem accessing shares.

The thing that your users might complain about, however, is their profiles. You might need to use some kind of profile migration tool (Windows has one built in) to move their local account profiles to their domain account profiles. They'll need their documents, their application settings, their outlook nickname file (our users were very attached to their outlook nickname file), and, depending on your environment, perhaps even their wallpaper.

Katherine Villyard
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    Halleluja, you have no idea how happy that makes me. I may end up using ForensIT for the profile migration since in this environment any changes are resisted. If I can make their shiny new domain profile look and act like their local one then the only argument I'll get is over the new username schema I'll be implementing. :) – Sootah Jan 02 '14 at 23:04
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    That damn nickname file caused me so many support calls...be sure they keep it or you will feel the users wrath! – Grant Jan 08 '14 at 00:47
  • Outlookprofilename.NK. Yes. – Katherine Villyard Jan 08 '14 at 03:03