How to migrate Workgroup with SBS 2003 to full AD domain with Exchange?

Question

My company's desktops, Linux and Windows servers, are all stand-alone, with nothing more than a workgroup to bind them. We also have an SBS 2003 server that is used for shared contacts/calendar and as a fileserver. This SBS server has a simple domain with a bunch of users and groups that are only used for the fileserver permissions, and for the Exchange login (only shared contacts/calendar). DNS is a BIND server and not integrated with the SBS2003.

I'm about to migrate and join all this to a Active Directory domain, based on Windows Server 2008 R2 which I've installed on a new virtual machine. I can install a separate 2008 R2 machine for Exchange 2010. I'd prefer to dump the old domain name, due to crappy naming and no decent design. Recreating the fileserver permissions will be easy, but I'd prefer to keep the user accounts and Exchange data.

I'm unsure how to proceed though, since I'm primarily a Linux admin.

Create a new forest and domain with the proper name, and migrate the users and groups via ADMT? Join all servers to the domain? Then migrate the Exchange data?

Or join the new server to the old domain, promote it and decommision the old one? Then somehow migrate the Exchange data? I'm not sure how well this would work without AD-aware DNS server.

Other ways I could do this? Any tips are welcome. Thanks.

Answer 1

There are probably at leat 6 different ways to do this. My opinion is that any attempt to "migrate" anything is going to be cumbersome and messy. I might suggest setting up a new forest\domain on the W2K8R2 server, installing Exchange, setting up identical user accounts\mailboxes, exporting the mailboxes from the old SBS2K3 server using exmerge and importing the resultant pst files into the new mailboxes.