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I run my own consulting software shop, and I'm currently running SBS 2008 Premium. I'm not utilizing the second server at the moment, but when I finally get to SBS 2011 Premium I'd like to. The server is already maxed at 4GB of ram, and I have six drives, one for the C: and the rest are part of a RAID 5 which is where all user data is stored (Sql dbs, Exchange data, file shares).

I'd like to get some new hardware that will eventually run SBS 2011.

My plan is to get the new hardware which will include disks for a RAID 5 and hardware virtualization support. I'll then install the second Windows 2008 Server license that comes with SBS 2008. I'd like to then move the current SBS server from physical hardware to a virtual on the new secondary server. This is one area I'm not sure of. Is it possible, and also what about the data on the RAID disks? Will that pose a problem?

Later when I have enough to buy the SBS2011, I'd upgrade the secondary 2008 server (running on the new physical hardware), then setup SBS2011 in a new virtual and migrate from 2008 to 2011.

Would this be a possible route to go? If not, what would be the best recommendation, given that there will be a delay between buying the new server hardware and buying the SBS2011 license.

EDIT: I'm planning on using the second server (not in use at all right now) to install 2008 HyperV on the new hardware, then pull the physical SBS into a virtual on the new hardware. I've never done a P2V before, so I'm not sure what to do about the data drive which is currently a RAID5 and where SBS2008 stores its Exchange data and user folder redirections.

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There is a migration guide for SBS 2011 which lists the supported migration path from 2008 to 2011. Basically, the only supported upgrade option is a fresh install of the SBS 2011 on new hardware in what is called "Upgrade Mode" (it will allow the SBS 2011 server to join the presently available SBS 2008 domain and pull all Active Directory data) and the wizard-assisted or manual migration of all data and server software from the old to the new server.

There is no in-place upgrade option for the SBS from any previously installed OS, you always have to deal with a fresh install.

If you virtualize, this will be not too much of a concern - you simply fire up a new virtual machine for your SBS 2011 installation. Make sure to get enough RAM for your physical machine - SBS 2011 is quite memory-hungry, expect a single instance to easily eat 16 GB of RAM.

I'd like to then move the current SBS server from physical hardware to a virtual on the new secondary server. This is one area I'm not sure of. Is it possible, and also what about the data on the RAID disks?

The name for this procedure is "physical-to-virtual" (P2V) conversion. You would have a different set of tools depending on the virtualization platform you are going to chose to accomplish this task. For VMWare virtualizaion products (vSphere ESXi), the VMWare converter is free and really easy to use, you will find a lot of walkthroughs and howtos on the net.

The converter tool will make it easy for you to copy the data off the old machine into the virtualized environment, the RAID volume content can be copied as any other volume's content. Typically, you are getting the choice to resize your partitions and filesystems as part of the conversion process.

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+1 - this is what I did when I did a 2008-2011 migration. P2V of the old 2008 machine, and then installed 2011 in a new VM on the same hardware. –  Mark Henderson Jan 28 '12 at 20:33
Thanks for the answer. It sounds like I should be ok with my plan then, as I'd use the second server from SBS for HyperV and install the 2011 primary server as a new virtual. The one thing I'm still unclear on is the existing data, which is a D: spread over a Raid5. Does that come though as a virtual disk on the new server? If not, how would the existing SBS continue to use it to store its Exchange and Sql server databases, as well as user folder redirections. –  Andy Jan 28 '12 at 20:48
@andy You do not need to use the second Server license for Hyper-V, the Hypervisor standalone is free, although rather comparable to a Server Core installation (you can't do much at the console, mostly you have to use remote management tools). You can't keep your current RAID5 as it is for the virtualized environment - you would create a copy of the filesystem to a virtual disk instead (which in turn can be on a RAID5-placed volume as well as on any other kind of volume). After copying, it would retain the drive letter assignment. –  the-wabbit Jan 28 '12 at 21:50
@syneticon-dj Thanks for the info. I wasn't necessarly looking to keep the RAID5 as it is, but I just wanted to make sure the data could come along fairly easily. Thanks for the link as well; I was going off SBS documentation which says I can use the second license as both the parent HyperV role only as well as a child where I could use it as intended. –  Andy Jan 29 '12 at 2:45

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